- Silver-Catalyzed C(sp3)-H Sulfonylation for the Synthesis of Benzyl Sulfones Using Toluene Derivatives and α-Amino Acid Sulfonamides
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We describe a simple and practical protocol for the synthesis of benzyl sulfones using readily available toluene derivatives and α-amino acid sulfonamides. The reaction proceeds to afford a broad range of benzyl sulfones in moderate to high yields under silver catalysis. The mechanism possibly involves a Minisci-type formation of α-aminoalkyl radical, homolytic cleavage of a N-S bond to generate a sulfonyl radical, and coupling of sulfonyl radical with a benzyl radical formed via hydrogen abstraction by sulfate anion radical. The practicality of the present reaction is demonstrated by a gram-scale synthesis and one-step synthesis of anticancer-active compound. The mechanism studies are conducted using radical scavengers and deuterated toluene.
- Kanyiva, Kyalo Stephen,Shibata, Takanori,Uchida, Kanako
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p. 1377 - 1384
(2021/06/06)
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- Access to Optically Pure Benzosultams by Superelectrophilic Activation
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Through superacid activation, N-(arenesulfonyl)-aminoalcohols derived from readily available ephedrines or amino acids undergo an intramolecular Friedel-Crafts reaction to afford enantiopure benzosultams bearing two adjacent stereocenters in high yields with fully controlled diastereoselectivity. Low-temperature NMR spectroscopy demonstrated the crucial role played by the conformationally restricted chiral dicationic intermediates.
- Michelet, Bastien,Castelli, Ugo,Appert, Emeline,Boucher, Maude,Vitse, Kassandra,Marrot, Jér?me,Guillard, Jér?me,Martin-Mingot, Agnès,Thibaudeau, Sébastien
-
supporting information
p. 4944 - 4948
(2020/07/14)
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- Synthesis, molecular docking and pharmacological investigation of some 4-methylphenylsulphamoyl carboxylic acid analogs
-
Compounds bearing sulphonyl and amino acid moieties are considered the basis for sulfa drug development. The synthesis of 4-methylphenylsulphamoyl carboxylic acids and the evaluation of their pharmacological activities are reported. The synthesis of these
- Egbujor, Melford C.,Okoro, Uchechukwu C.,Okafor, Sunday N.,Amasiatu, Ifeanyi S.,Amadi, Ugochukwu B.,Egwuatu, Pius I.
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p. 5357 - 5366
(2020/10/12)
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- Synthesis and biological evaluation of alanine derived bioactive P-toluenesulphonamide analogs
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Sulphonamides and carboxamides have great pharmacological importance. The purpose of the study was to synthesize alanine-derived bioactive sulphonamides bearing carboxamides and evaluate their biological activi-ties. The reaction of p-toluenesulphonyl chloride with L-alanine afforded compound 1, which was acetylated to obtain compound 2. The chlorina-tion and ammonolysis of compound 2 gave the carboxamide backbone (3) which was coupled with aryl/heteroaryl halides to afford the hybrid compounds 4, 5 and 6. Structures were confirmed by FTIR,1 H-NMR,13 C-NMR spectra and elemental analytical data. The in vitro antimicrobial properties were determined by agar dilution, and the antioxidant properties were also investigated. Molecular docking interactions of the analogues were determined using PyRx. Compounds 4, 5 and 6 exhibited excellent in vitro antimi-crobial properties in the range of 0.5-1.0mg/ml while compounds 1and 2 had half-maximal inhibitory concentration (IC50) of 1.11±0.15μg/ml and 1.12±0.13μg/ml respectively. For the molecular docking studies, compounds 5 and 6 displayed the best antitrypanosomal activity with binding affinities of-13.95 and-13.51kcal/mol respectively while compound 4 showed the highest in silico antimalarial activity having binding affinity of-11.95kcal/mol. All the alanine derived sulphonamides were observed to be potential antimicrobial, antioxidant, antitrypanosomal and antimalarial agents following the biological activities studies.
- Amasiatu, Ifeanyi S.,Egbujor, Melford C.,Egu, Samuel A.,Egwuatu, Pius I.,Eze, Florence U.,Okoro, Uchechukwu C.
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p. 6449 - 6458
(2020/10/27)
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- Synthesis and Structure-Activity Relationships of Arylsulfonamides as AIMP2-DX2 Inhibitors for the Development of a Novel Anticancer Therapy
-
AIMP2-DX2, a splicing variant of AIMP2, is up-regulated in lung cancer, possesses oncogenic activity, and results in tumorigenesis. Specifically inhibiting the interaction between AIMP2-DX2 and HSP70 to suppress AIMP2-DX2-dependent cancers with small molecules is considered a promising avenue for cancer therapeutics. Optimization of hit BC-DXI-04 (IC50 = 40.1 μM) provided new potent sulfonamide based AIMP2-DX2 inhibitors. Among these, BC-DXI-843 showed improved inhibition against AIMP2-DX2 (IC50 = 0.92 μM) with more than 100-fold selectivity over AIMP2 in a luciferase assay. Several binding assays indicated that this compound effectively induces cancer cell apoptosis by specifically interrupting the interaction between DX2 and HSP70, which leads to the degradation of DX2 via Siah1-mediated ubiquitination. More importantly, BC-DXI-843 demonstrated in vivo efficacy in a tumor xenograft mouse model (H460 cells) at a dosage of 50 mg/kg, suggesting it as a promising lead for development of novel therapeutics targeting AIMP2-DX2 in lung cancer.
- Sivaraman, Aneesh,Kim, Dae Gyu,Bhattarai, Deepak,Kim, Minkyoung,Lee, Hwa Young,Lim, Semi,Kong, Jiwon,Goo, Ja-Il,Shim, Seunghwan,Lee, Seungbeom,Suh, Young-Ger,Choi, Yongseok,Kim, Sunghoon,Lee, Kyeong
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p. 5139 - 5158
(2020/05/05)
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- Synthesis and hetero-Diels-Alder reactions of enantiomerically pure dihydro-1: H -azepines
-
Thermolysis of enantiomerically pure 3-substituted 7,7-dihalo-2-azabicyclo[4.1.0]heptanes in the presence of K2CO3 gives in good yields 2-alkyl-6-halo-1-tosyl-2,3-dihydro-1H-azepines. These undergo highly stereoselective [4+2] cycloaddition reactions with heterodienophiles and arylation/alkenylation under Suzuki conditions.
- Craig, Donald,Spreadbury, Samuel R. J.,White, Andrew J. P.
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supporting information
p. 9803 - 9806
(2020/09/16)
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- New peptide derived antimalaria and antimicrobial agents bearing sulphonamide moiety
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Fourteen novel dipeptide carboxamide derivatives bearing benzensulphonamoyl propanamide were synthesized and characterized using 1H NMR, 13C NMR, FTIR and MS spectroscopic techniques. In vivo antimalarial and in vitro antimicrobial studies were carried out on these synthesized compounds. Molecular docking, haematological analysis, liver and kidney function tests were also evaluated to assess the effect of the compounds on the organs. At 200 mg/kg body weight, 7i inhibited the multiplication of the parasite by 81.38% on day 12 of post-treatment exposure. This was comparable to the 82.34% reduction with artemisinin. The minimum inhibitory concentration (MIC) in μM ranged from 0.03 to 2.34 with 7h having MIC of 0.03 μM against Plasmodium falciparium. The in vitro antibacterial activity of the compounds against some clinically isolated bacteria strains showed varied activities with some of the new compounds showing better activities against the bacteria and the fungi more than the reference drug ciprofloxacin and fluconazole.
- Ugwuja,Okoro,Soman,Soni,Okafor,Ugwu
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p. 1388 - 1399
(2019/08/22)
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- Iodine-Catalyzed Synthesis of Chiral 4-Imidazolidinones Using α-Amino Acid Derivatives via Dehydrogenative N-H/C(sp3)-H Coupling
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An efficient method for the asymmetric synthesis of 4-imidazolidinones via an iodine-catalyzed intramolecular N-H/C(sp3)-H activation of readily available and abundant feedstocks, amino acids, and amines is described. The reaction proceeded under visible light irradiation to afford a variety of 4-imidazolidinone derivatives under mild conditions in moderate to excellent yields. Secondary and tertiary C(sp3)-H bonds were aminated, and various functional groups were tolerated.
- Kanyiva, Kyalo Stephen,Tane, Marina,Shibata, Takanori
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p. 12773 - 12783
(2019/09/09)
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- Synthesis of Tripeptide Derivatives with Three Stereogenic Centers and Chiral Recognition Probed by Tetraaza Macrocyclic Chiral Solvating Agents Derived from d -Phenylalanine and (1 S,2 S)-(+)-1,2-Diaminocyclohexane via 1H NMR Spectroscopy
-
Enantiomers of a series of tripeptide derivatives with three stereogenic centers (±)-G1-G9 have been prepared from d- and l-α-amino acids as guests for chiral recognition by 1H NMR spectroscopy. In the meantime, a family of tetraaza macrocyclic chiral solvating agents (TAMCSAs) 1a-1d has been synthesized from d-phenylalanine and (1S,2S)-(+)-1,2-diaminocyclohexane. Discrimination of enantiomers of (±)-G1-G9 was carried out in the presence of TAMCSAs 1a-1d by 1H NMR spectroscopy. The results indicate that enantiomers of (±)-G1-G9 can be effectively discriminated in the presence of TAMCSAs 1a-1d by 1H NMR signals of multiple protons exhibiting nonequivalent chemical shifts (ΔΔδ) up to 0.616 ppm. Furthermore, enantiomers of (±)-G1-G9 were easily assigned by comparing 1H NMR signals of the split corresponding protons with those attributed to a single enantiomer. Different optical purities (ee up to 90%) of G1 were clearly observed and calculated in the presence of TAMCSAs 1a-1d, respectively. Intermolecular hydrogen bonding interactions were demonstrated through theoretical calculations of enantiomers of (±)-G1 with TAMCSA 1a by means of the hybrid functional theory with the standard basis sets of 3-21G of the Gaussian 03 program.
- Feng, Lei,Gao, Guangpeng,Zhao, Hongmei,Zheng, Li,Wang, Yu,Stavropoulos, Pericles,Ai, Lin,Zhang, Jiaxin
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p. 13874 - 13887
(2018/11/23)
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- Pd(ii)-Catalyzed aerobic 1,2-difunctionalization of conjugated dienes: Efficient synthesis of morpholines and 2-morpholones
-
A novel and efficient methodology concerning the Pd(ii)-catalyzed intermolecular difunctionalization of conjugated dienes is reported to synthesize a series of functionalized morpholines and 2-morpholones. Widely distributed and easily obtained β-amino alcohols and α-amino acids, as starting nitrogen and oxygen sources, are successfully applied in the difunctionalization of conjugated dienes respectively. The majority of the desired products were obtained in moderate to excellent yields. Oxygen was successfully employed as a terminal oxidant. Further transformation of the generated products allowed for the expansion of structural diversity.
- Wen, Ke,Wu, Zhengxing,Chen, Buyun,Chen, Jianzhong,Zhang, Wanbin
-
supporting information
p. 5618 - 5625
(2018/08/17)
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- Palladium-catalyzed site-selective hydrogen isotope exchange (HIE) reaction of arylsulfonamides using amino acid auxiliary
-
Hydrogen isotope exchange (HIE) is a versatile method for the introduction of deuterium to organic compounds. Herein, regioselective deuteration of sulfonamides is achieved by palladium-Catalyzed HIE reaction. By using amino acid as weakly coordination-di
- Liu, Wei,Xu, Xingyu,Zhao, Hongyan,Yan, Xiaoyu
-
p. 4111 - 4118
(2018/06/19)
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- α-Amino Acid Sulfonamides as Versatile Sulfonylation Reagents: Silver-Catalyzed Synthesis of Coumarins and Oxindoles by Radical Cyclization
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We developed a silver-catalyzed strategy for the generation of sulfonyl radicals from sulfonamides derived from α-amino acids. The reaction proceeded via a decarboxylation, N–S bond cleavage and radical cyclization sequence and allows the difunctionalization of alkynes and the synthesis of 3-sulfonylated coumarins. The reaction tolerated a broad scope of substrates and functional groups and could be extended to the synthesis of oxindoles and an isoquinolinedione by the capturing of the sulfonyl radical with an alkene moiety. Moreover, the proposed mechanism was supported experimentally and by DFT calculations.
- Kanyiva, Kyalo Stephen,Hamada, Daisuke,Makino, Sohei,Takano, Hideaki,Shibata, Takanori
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supporting information
p. 5905 - 5909
(2018/09/14)
-
- Synthesis of Enantiopure PZM21: A Biased Agonist of the Mu-Opioid Receptor
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PZM21 (1) was recently reported as a biased agonist of the mu-opioid receptor (MOR) with improved antinociceptive effects and reduced side effects compared with traditional opioid-based analgesics. The original synthesis of PZM21 with the desired (S,S) configuration required the separation of a diastereomeric mixture in the final step by using chiral HPLC. A concise synthesis of 1 has now been developed in the enantiomeric pure form starting with commercially available l-alanine and proceeding via a chiral aziridine as a key intermediate. The final product was obtained as the (S,S) diastereomer in seven steps in 22.5 % yield from l-alanine. This synthetic strategy could be readily applied to the development of PZM21 analogues at the thiophenyl position.
- Perrey, David,Zhang, Dehui,Nguyen, Thuy,Carroll, F. Ivy,Ko, Mei-Chuan,Zhang, Yanan
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p. 4006 - 4012
(2018/07/30)
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- Metal-Free N–H/C–H Coupling for Efficient Asymmetric Synthesis of Chiral Dihydroquinoxalinones from Readily Available α-Amino Acids
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We have developed a method for the synthesis of dihydroquinoxalinones via intramolecular N–H/C–H coupling using hypervalent iodine. The starting materials were prepared from inexpensive and readily available aniline and amino acid derivatives. Various functional groups were tolerated to give multisubstituted dihydroquinoxalinones in moderate to excellent yields. The chirality of the amino acid was transferred to the desired target compound without a loss of enantiomeric excess. Preliminary mechanistic studies indicated that the reaction proceeds via an ionic mechanism.
- Kanyiva, Kyalo Stephen,Horiuchi, Masashi,Shibata, Takanori
-
supporting information
p. 1067 - 1070
(2018/03/06)
-
- Direct Catalytic Chemoselective α-Amination of Acylpyrazoles: A Concise Route to Unnatural α-Amino Acid Derivatives
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A direct copper-catalyzed highly chemoselective α-amination is described. Acylpyrazole proved to be a highly efficient enolate precursor of a carboxylic acid oxidation state substrate, while preactivation by a stoichiometric amount of strong base has been used in catalytic α-aminations. The simultaneous activation of both coupling partners, enolization and metal nitrenoid formation, was crucial for obtaining the product, and wide functional group compatibility highlighted the mildness of the present catalysis. The bidentate coordination mode was amenable to highly chemoselective activation over ketone and much more acidic nitroalkyl functionality. Deuterium exchange experiments clearly demonstrated that exclusive enolization of acylpyrazole was achieved without the formation of a nitronate. The present catalysis was applied to late-stage α-amination, allowing for concise access to highly versatile α-amino acid derivatives. The product could be transformed into variety of useful building blocks.
- Tokumasu, Keisuke,Yazaki, Ryo,Ohshima, Takashi
-
supporting information
p. 2664 - 2669
(2016/03/12)
-
- Palladium-Catalyzed Mono-Selective ortho C H Arylation of Aryl Sulfonamides in Water: A Concise Access to Biaryl Sulfoamide Derivatives
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A green atom-economical method for the synthesis of biaryl sulfonamide derivatives via palladium(II)-catalyzed C H bond activation by employing an amino acid moiety as the bidentate directing group has been developed. The protocol proceeded efficiently in water; high yields and broad substrate scope were achieved. The reaction shows good functional group compatibility and proceeds in a highly selective manner at the ortho position of arenes connected to sulfonamide sulfur atoms. This auxiliary can be easily removed either by acidic hydrolysis, or converted into primary biaryl sulfomamides with a 30 mol % amount of CuO as catalyst. Mechanistic studies show that the present bidentate directing group is essential for promoting ortho C H bond activation of arenes connected to sulfonamide sulfur atoms. (Figure presented.) .
- Liu, Wei,Wang, Dongyin,Zhao, Yongli,Yi, Fei,Chen, Junmin
-
supporting information
p. 1968 - 1974
(2016/07/06)
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- Cu(II)-catalyzed decarboxylation/elimination of N-arylsulfonyl amino acids to primary aryl sulfonamides
-
A novel protocol for CuO-catalyzed decarboxylation/elimination of N-arylsulfonyl amino acids was developed. It is the first example of using an accessible amino acid as an ammonia synthetic equivalent for the synthesis of primary aryl sulfonamides via oxidative decarboxylation/elimination reactions. The present protocol shows excellent functional group tolerance and provides an efficient method for the synthesis of primary aryl sulfonamides in excellent yields.
- Zhou, Liandi,Li, Xiaokang,Liu, Wei,Zhao, Yongli,Chen, Junmin
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supporting information
p. 1299 - 1306
(2016/08/16)
-
- Synthesis of Six- and Seven-Membered Chloromethyl-Substituted Heterocycles via Palladium-Catalyzed Amino- and Oxychlorination
-
The synthesis of six- and seven-membered chloromethyl-substituted heterocycles, such as piperazinone, tetrahydroquinoxaline, benzodiazepinone, and benzoxazepinone, is reported using palladium-catalyzed vicinal diheterofunctionalization of nonactivated alkenes. The reaction conditions for this domino process are soft and mild, and the chloromethyl appendage allows various post-functionalizations via simple nucleophilic substitutions.
- Manick, Anne-Doriane,Berhal, Farouk,Prestat, Guillaume
-
supporting information
p. 3719 - 3729
(2016/11/08)
-
- Palladium-Catalyzed Modular Synthesis of Substituted Piperazines and Related Nitrogen Heterocycles
-
We report here a novel method for the modular synthesis of highly substituted piperazines and related bis-nitrogen heterocycles via a palladium-catalyzed cyclization reaction. The process couples two of the carbons of a propargyl unit with various diamine components to provide nitrogen heterocycles in generally good to excellent yields and high regio- and stereochemical control. (Chemical Equation Presented).
- Montgomery, Thomas D.,Rawal, Viresh H.
-
supporting information
p. 740 - 743
(2016/03/01)
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- Metal complexes of tosyl sulfonamides: Design, X-ray structure, biological activities and molecular docking studies
-
The present study reports the synthesis of Zn(ii) complexes of tosyl sulfonamide derivatives obtained by the reaction of tosyl chloride with l-amino acids. The ligands and their complexes were characterized by IR, 1H and 13C-NMR, GC-
- Khan, Najm Ul Hassan,Zaib, Sumera,Sultana, Kishwar,Khan, Imtiaz,Mougang-Soume, Berline,Nadeem, Humaira,Hassan, Mukhtiar,Iqbal, Jamshed
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p. 30125 - 30132
(2015/05/13)
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- Aqueous MW eco-friendly protocol for amino group protection
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In this paper a new catalyst-free and on-water method for protection of amines and amino acids with di-tert-butyl dicarbonate, 9-fluorenylmethoxycarbonyl chloride, acetyl chloride and tosyl chloride is presented. The protection can be realized in a few minutes under microwave-assistance. The reaction proved to be chemoselective in presence of ambident nucleophiles and water solution of di-tert-butyl carboxylic acid or chloride acid are the only wastes produced.
- Nardi,Cano, N. Herrera,Costanzo,Oliverio,Sindona,Procopio
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p. 18751 - 18760
(2015/06/15)
-
- Aryl λ3-Iodane-Mediated 6-exo-trig Cyclization to Synthesize Highly Substituted Chiral Morpholines
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A mild and efficient transition metal-free approach has been developed for the synthesis of highly substituted chiral morpholines from alkenols by amino acid-derived iodine(III) reagents via a 6-exo-trig cyclization. The key features of this work include
- Kishorevandavasi, Jaya,Hu, Wan-Ping,Chandrusenadi, Gopal,Chen, Hui-Ting,Chen, Hsing-Yin,Hsieh, Kuang-Chan,Wang, Jeh-Jeng
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supporting information
p. 2788 - 2794
(2015/09/28)
-
- Conversion of alanine and phenylalanine into weinreb amides by using different protecting groups
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Efficient conversions of amino acids into Weinreb amides were achieved by treatment of amino acids with N,O-dimethylhydroxylamine hydrochloride in basic media. The amino group (-NH2) of amino acids were protected with p-toluene sulphonyl chlori
- Ali, Zulfiqar,Gilani, Syeda Rubina,Hussain, Habib,Hussain, Imdad
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p. 6733 - 6736
(2015/02/19)
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- Synthetically amenable amide derivatives of tosylated-amino acids as organocatalysts for enantioselective allylation of aldehydes: Computational rationale for enantioselectivity
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A phenylalanine derived chiral amide is developed that serves as an effective organocatalyst for the reaction of allyltrichlorosilane with aryl, hetero-aryl and α,β-unsaturated aldehydes to afford the desired homoallylic alcohols in good yield (up to 90%)
- Ghosh, Debashis,Sahu, Debashis,Saravanan,Abdi, Sayed H. R.,Ganguly, Bishwajit,Khan, Noor-Ul H.,Kureshy, Rukhsana I.,Bajaj, Hari C.
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p. 3451 - 3460
(2013/06/05)
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- 1,5-rhodium shift in rearrangement of N -arenesulfonylazetidin-3-ols into benzosultams
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Benzosultams are synthesized in an enantiopure form starting from α-amino acids through a rhodium-catalyzed rearrangement reaction of N-arenesulfonylazetidin-3-ols. Mechanistically, this reaction involves C-C bond cleavage by β-carbon elimination and C-H bond cleavage by a 1,5-rhodium shift.
- Ishida, Naoki,Shimamoto, Yasuhiro,Yano, Takaaki,Murakami, Masahiro
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supporting information
p. 19103 - 19106
(2014/01/17)
-
- Stereoselective synthesis and applications of nitrogen substituted donor-acceptor cyclopropanes (N-DACs) in the divergent synthesis of azacycles
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A new, highly stereoselective intramolecular cyclopropanation of vinylogous carbamates with carbenes in the presence of Cu(acac)2 as the catalyst has been developed for the construction of cyclopropapyrrolidinones. The 'syn' isomer of N-DAC can be converted to the 'anti' isomer by simple silica gel treatment. Regioselective cleavage of each of the cyclopropane bonds of these two acceptor substituted N-DACs led to a diverse array of azacycles.
- Gharpure, Santosh J.,Vijayasree,Reddy, S. Raja Bhushan
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supporting information; scheme or table
p. 1735 - 1738
(2012/04/17)
-
- Synthesis, characterization, and biological activity of five new mixed-ligand palladium(II) complexes with ethylenediamine and 4-toluenesulfonyl-L-amino acid dianion
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Five new palladium(II) complexes with 4-toluenesulfonyl-L-amino acid dianion and en, [Pd(en)(TsserNO)] (1), [Pd(en)(TsglyNO)] (2), [Pd(en)(TsalaNO)]·1.5H2O (3), [Pd(en)(TsleuNO)]·H 2O (4), and [Pd(en)(TspheNO)]·2H2O (5), have been synthesized and characterized by elemental analysis, IR, UV, 1H NMR, and mass spectrometry. Crystal structure of 1 has been determined by X-ray diffraction analysis. The cytotoxicity was tested by MTT and SRB assays. The results indicate 1-5 exert cytotoxic effects against HL-60, Bel-7402, BGC-823, and KB cell lines and 5 displays the best cytotoxicity. The structure-activity relationships suggest that both amino acid and N-containing ligands have important effects on cytotoxicity. Copyright
- Zhang, Jinchao,Ma, Lili,Zhang, Fangfang,Zhang, Zhilei,Li, Luwei,Wang, Shuxiang
-
experimental part
p. 239 - 250
(2012/06/01)
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- C2-symmetric recyclable organocatalyst for enantioselective Strecker reaction for the synthesis of α-amino acid and chiral diamine-an intermediate for APN inhibitor
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Recyclable chiral amide-based organocatalyst 5 efficiently catalyzed asymmetric Strecker reaction of various aromatic and aliphatic N-benzhydrylimines with ethyl cyanoformate as cyanide source at -10 °C to give a high yield (95%) of α-aminonitriles with excellent chiral induction (ee, up to 99%) with the added advantage of recyclability. Based on experimental observations a probable mechanism was proposed for this reaction. This protocol with catalyst 5 was extended for the synthesis of (R)-phenylalanine and pharmaceutically important drug intermediate (R)-3-phenylpropane-1,2-diamine in high yield with high enantioselectivity.
- Saravanan,Sadhukhan, Arghya,Khan, Noor-Ul H.,Kureshy, Rukhsana I.,Abdi, Sayed H. R.,Bajaj, Hari C.
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experimental part
p. 4375 - 4384
(2012/06/30)
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- Stereoselective synthesis of morpholines via copper-promoted oxyamination of alkenes
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A new copper(II) 2-ethylhexanoate-promoted addition of an alcohol and an amine across an alkene (oxyamination) is reported. The alcohol addition is intramolecular, while coupling with the amine occurs intermolecularly. Several 2-aminomethyl morpholines we
- Sequeira, Fatima C.,Chemler, Sherry R.
-
supporting information
p. 4482 - 4485
(2012/10/29)
-
- Synthesis, characterization and cytotoxicity of platinum(II)/palladium(II) complexes with 1,3-diaminopropane and 4-toluensulfonyl-l-amino acid dianion
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Eight novel platinum(II)/palladium(II) complexes with 1,3-dap and 4-toluensulfonyl-l-amino acid dianion, [Pt(1,3-dap)(TsalaNO)]·0.5H 2O (1a), [Pt(1,3-dap)(TsvalNO)] (1b), [Pt(1,3-dap)(TspheNO)] (1c), [Pt(1,3-dap)(TsserNO)] (1d), [Pd(1,3-dap)(Ts
- Zhang, Jinchao,Ma, Lili,Lu, Huiru,Wang, Yuechai,Li, Shenghui,Wang, Shuxiang,Zhou, Guoqiang
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p. 281 - 286
(2013/02/23)
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- ZnO and ZnO-nanoparticles: Efficient and reusable heterogeneous catalysts for one-pot synthesis of N-acylsulfonamides and sulfonate esters
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Commercially available and preparative ZnO nanoparticles are reported as efficient and reusable catalysts for the chemoselective synthesis of N-acylsulfonamides and sulfonate esters. A one-pot sequential sulfonylation and acylation of amines took place to afford the N-acylsulfonamides in excellent yields under solvent-free conditions. The ZnO catalyst can be reused for without significant loss of catalytic activity.
- Tamaddon, Fatemeh,Sabeti, Mohammad Reza,Jafari, Abbas Ali,Tirgir, Farhang,Keshavarz, Elham
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experimental part
p. 41 - 45
(2012/01/12)
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- A modified synthetic approach to optically pure benzoxazepines from amino acid precursors using intramolecular buchwald-hartwig C-O bond-formation reaction
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Palladium-catalyzed intramolecular aryl etherification reaction using bulky binaphthylphosphane ligand is shown to be a convenient method for the synthesis of seven-membered heterocycles. Application of this methodology to a naturally occurring proteinoge
- Bhattacharya, Debleena,Behera, Ashok,Hota, Sandip K.,Chattopadhyay, Partha
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scheme or table
p. 585 - 592
(2011/04/12)
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- Diversity-oriented synthesis based on the dppp-catalyzed mixed double-michael reactions of electron-deficient acetylenes and β-amino alcohols
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In this study, we prepared oxizolidines through 1,3-bis(diphenylphosphino)- propane (DPPP)-catalyzed mixed double-Michael reactions of β-amino alcohols with electron-deficient acetylenes. These reactions are very suitable for the diversity-oriented parallel syntheses of oxizolidines because: (i) they are performed under mild metal-free conditions and (ii) the products are isolated without complicated work-up. To demonstrate the applicability of mixed double-Michael reactions for the preparation of five-membered-ring heterocycles, we prepared 60 distinct oxazolidines from five β-amino alcohols and 12 electron-deficient acetylenes. We synthesized 36 of these 60 oxazolidines in enantiomerically pure form from proteinogenic amino acid-derived β-amino alcohols.
- Fan, Yi Chiao,Kwon, Ohyun
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scheme or table
p. 3802 - 3825
(2011/06/24)
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- Synthesis, characterization and cytotoxicity of mixed-ligand complexes of palladium(II) with 2, 2′-biquinoline/1, 4-diaminobutane and 4-toluenesulfonyl-L-amino acid dianion
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Seven new palladium(II) complexes (1-7) with 4-toluenesulfonyl-L-amino acid dianion and 2, 2′-biquinoline (bqu)/1,4-diaminobutane (dab) have been synthesized and characterized by elemental analysis, IR, 1H NMR, and mass spectra techniques. Crys
- Zhang, Jinchao,Li, Luwei,Ma, Lili,Zhang, Fangfang,Zhang, Zhilei,Wang, Shuxiang
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experimental part
p. 5711 - 5716
(2011/12/14)
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- Synthesis of constrained peptidomimetics containing 2-oxo-1,3-oxazolidine- 4-carboxylic acids
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Sulfonyl peptides containing a serine or threonine residue undergo cyclization with bis(succinimidyl) carbonate (DSC) and diisopropylethylamine (DIPEA) to give peptides with a 2-oxo-1,3-oxazolidine-4-carboxylate (Oxd) group, either in solution or in the solid phase. The position of the serine or threonine residue in the sequence is relatively unimportant. Under the same conditions, the corresponding Fmoc- or Boc-peptides gave dehydration products, in agreement to previous studies. The protocol constitutes a valuable approach to the preparation of oxazolidinone-containing peptides, which are a recently emerging class of constrained peptidomimetics. As a representative example, an Oxd analogue of the endogenous opioid peptide endomorphin-1, characterized by an all-trans conformation, was readily prepared.
- Gentilucci, Luca,Tolomelli, Alessandra,De Marco, Rossella,Tomasini, Claudia,Feddersen, Soeren
-
body text
p. 4925 - 4930
(2011/10/31)
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- Reductive aldol and mannich-type reactions of azetidin-3-ones promoted by titanium tetraiodide
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A convenient method is described for the generation and reaction of the enolates of aminoacetone equivalents, which uses the reduction of azetidin-3-one with titanium tetraiodide and subsequent reactions with electrophiles. This methodology provides a str
- Hata, Shingo,Fukuda, Daisuke,Hachiya, Iwao,Shimizu, Makoto
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supporting information; experimental part
p. 473 - 477
(2010/08/23)
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- Synthesis, characterization and cytotoxicity of mixed-ligand complexes of palladium(II) with aromatic diimine and 4-toluenesulfonyl-l-amino acid dianion
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Eight new palladium(II) complexes (1a-2d) with 4-toluenesulfonyl-l-amino acid dianion and diimine (bipy and phen) have been synthesized and characterized by elemental analysis, IR, UV, 1H NMR, 13C NMR and mass spectra techniques. Cry
- Zhang, Jinchao,Li, Luwei,Wang, Liwei,Zhang, Fangfang,Li, Xiaoliu
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experimental part
p. 5337 - 5344
(2011/01/04)
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- Copper(II) triflate-catalyzed intramolecular hydroamination of homoallylic amino alcohols as an expedient route to trans-2,5-dihydro-1H-pyrroles and 1,2-dihydroquinolines
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A new efficient synthetic route to trans-2,5-dihydro-1H-pyrroles and 1,2-dihydroquinolines that relies on copper(II) triflate-catalyzed intramolecular hydroamination of homoallylic amino alcohols under mild and operationally straightforward conditions is
- Rao, Weidong,Kothandaraman, Prasath,Koh, Chii Boon,Chan, Philip Wai Hong
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supporting information; experimental part
p. 2521 - 2530
(2011/02/21)
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- Synthesis of some sulphonamide insect juvenile hormone - Part I
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Regular use of classical insecticides has drastically effected the environment and warm blooded animals. Therefore, there is an urgent need to look for a kind of chemicals which are very specific, targeted in their action and environment friendly. Since l
- Awasthi, Pamita,Mahajan
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p. 1291 - 1297
(2008/12/23)
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- Synthesis, anti-HIV, and antifungal activity of new benzensulfonamides bearing the 2,5-disubstituted-1,3,4-oxadiazole moiety
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A series of novel chiral and achiral N-[1-(1,3,4-oxadiazol-2ylthio)alkyl]- 4-methyl/chloro/methoxybenzenesulfonamides 5a-l were prepared by the reaction of 4-(4-methyl, chloro, methoxyphenylsulfonamido)alkyl carboxylic acid hydrazides 4a-l with CS2 and KO
- Zareef, Muhammad,Iqbal, Rashid,Al-Masoudi, Najim A.,Zaidi, Javid H.,Arfan, Muhammad,Shahzad, Sohail A.
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p. 281 - 298
(2007/10/03)
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- β-cyclodextrin-catalyzed monosulfonylation of amines and amino acids in water
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A mild and efficient procedure has been developed for the first time under biomimetic conditions for the monosulfonylation of various amines and amino acids catalyzed by β-cyclodextrin in water at room temperature to afford the corresponding sulfonamides in high yields.
- Sridhar,Srinivas,Kumar, V. Pavan,Narender,Rao, K. Rama
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p. 1873 - 1876
(2008/09/16)
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- Stereoselective γ-lactam synthesis via palladium-catalysed intramolecular allylation
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A novel route to the synthesis of 3-(tolylsulfonyl)-4,5-cis-disubstituted γ-lactams using a diastereoselective palladium-catalysed intramolecular allylation of amino acid-derived allylic carbonates has been developed. The Royal Society of Chemistry 2005.
- Craig, Donald,Hyland, Christopher J. T.,Ward, Simon E.
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p. 3439 - 3441
(2007/10/03)
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- Synthesis and Structural Characterization of Trivalent Amino Acid Derived Chiral Phosphorus Compounds
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Reaction of the N-toluenesulfonyl derivatives of (S)-alanine, phenylalanine, and valine (4-6) with PhPCl2 gave in high yield the 4-methyl, benzyl, and isopropyl derivatives (7-9) of 2-phenyl-1-p-toluenesulfonyl-1,3,2-oxazaphospholidin-5-one. Th
- Hersh, William H.,Xu, Ping,Simpson, Cheslan K.,Grob, Jonathan,Bickford, Brian,Hamdani, Mohammad Salman,Wood, Thomas,Rheingold, Arnold L.
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p. 2153 - 2163
(2007/10/03)
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- Synthesis and structure of lower rim C-linked N-tosyl peptidocalix[4]arenes
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Chiral p-tert-butylcalix[4]arenes functionalized at the lower rim with amino acid residues have been prepared. The 1H and 13C NMR spectra indicate that the macrocycles preferably adopt a cone conformation. Calix[4]arenes bearing amin
- Sdira, Sofiane Ben,Felix, Caroline P.,Giudicelli, Marie-Beatrice A.,Seigle-Ferrand, Pascal F.,Perrin, Monique,Lamartine, Roger J.
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p. 6632 - 6638
(2007/10/03)
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- A new access to 3,5-disubstituted piperazinones via Pd(0)-catalyzed amination
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An original synthetic route toward 3,5-disubstituted piperazinones has been developed. The method relies upon a 6-exo intramolecular process between a sulfonylated nitrogen atom of amino acid derivation and an η3-allyl-palladium moiety. This cyclization process generates the two possible (cis and trans) diastereoisomers whose ratio depends on the amino acid employed. The bulkier the amino acid residue, the higher the observed cis:trans ratio. Convincing evidence for reversible intramolecular addition of the nitrogen nucleophile to the η3-allyl-palladium complex is put forward.
- Ferber, Benoit,Lemaire, Sébastien,Mader, Mary M.,Prestat, Guillaume,Poli, Giovanni
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p. 4213 - 4216
(2007/10/03)
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- Composition and device for detecting leukocytes in urine
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Thiazole esters are suitable for detecting the presence of leukocytes in urine. Such thiazole esters are suitable for use in compositions, diagnostic devices, and methods for detecting the presence of leukocytes. In one embodiment, a thiazole ester is of
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- Amino acids in the syntheses of heterocyclic systems: Syntheses and radiostability of novel biologically active triazoles containing the sulfonamide moiety
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A number of novel triazoles 2a-f, 4, 9, 10, 12, 15; triazolothiadiazoles 6, 8, 11, 16; triazolothiadizine 5; and triazolotriazine 14 were synthesized and characterized by elemental analyses and spectral data. Six of the compounds showed antifungal activity compared with the fungicide Mycostatine. Radiosterilization of the biologically active compounds 4, 8, 9b, and 10 in the dry state may prove to be applicable at the sterile dose 25 kGy.
- El-Sharief,Ghorab,El-Gaby,Mohamed,Ammar
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p. 316 - 323
(2007/10/03)
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- Synthesis of a [2]benzazepine analogue of clavizepine
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The synthesis of N-tosylbenzopyran[2]benzazepinone 2 using a simple protocol for assembly of an azepine ring on the xanthene skeleton is described. Formation of the C-C bond between C9 of the xanthen-9-ol 7 and the β-C of N-tosyl aminoacetaldehyde dimethyl acetal leads to 10, which upon treatment with formaldehyde undergoes ring closure.
- García, Alberto,Paz, Sonia,Domínguez, Domingo
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p. 665 - 667
(2007/10/03)
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- A new convenient approach to chiral β-aryl(heteroaryl)alkylamines
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Chiral β-aryl(heteroaryl)alkylamines have been prepared from N-tosyl alkylaziridines via regiospecific nucleophilic ring opening and subsequent desulfonylation in good to excellent yields. The corresponding aziridines are easily obtained from commercially available (S)-α-amino acids, so this method is the first effective route to asymmetric β-aryl(heteroaryl)alkylamines.
- Nenajdenko, Valentine G,Karpov, Alexei S,Balenkova, Elizabeth S
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p. 2517 - 2527
(2007/10/03)
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- Enantioselective addition of diethylzinc to aldehydes catalyzed by titanium(IV) complexes of N-sulfonylated amino alcohols with two stereogenic centers
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Bidentate N-sulfonylated amino alcohols with one or two stereogenic centers were prepared and applied as chiral ligands in the titanium(IV)-catalyzed asymmetric addition of diethylzinc to aldehydes, affording excellent enantioselectivities of up to 98% e.e.
- You, Jing-Song,Shao, Ming-Yuan,Gau, Han-Mou
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p. 2971 - 2975
(2007/10/03)
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