- Synthesis of 1,2,4,5-tetrasubstituted imidazoles and 2,4,5,6-tetrasubstituted pyrimidines: three-component, the one-pot reaction of arylamidines, malononitrile, and arylglyoxals or aryl aldehydes
-
A highly efficient one-pot synthesis of the 1,2,4,5-tetrasubstituted imidazoles and 2,4,5,6-tetrasubstituted pyrimidines through an arylamidine, malononitrile, and carbonyl compound by using Et3N in CH3CN at reflux conditions was dev
- Alizadeh-Bami, Farzaneh,Hajipour, Mina,Mehrabi, Hossein,Rezazadeh-Jabalbarezi, Fatemeh
-
-
Read Online
- Phosphorescent Cyclometalated Platinum(II) aNHC Complexes
-
The synthesis and characterization of the first bidentate C^C* cyclometalated platinum(II) complexes based on abnormal N-heterocyclic carbenes (aNHC) is presented. The aNHC ligand precursors are prepared from benzonitriles and anilines to form 1,2,3-trisu
- Soellner, Johannes,Strassner, Thomas
-
-
Read Online
- Combination of air/moisture/ambient temperature compatible organolithium chemistry with sustainable solvents: Selective and efficient synthesis of guanidines and amidines
-
Highly-efficient and selective fast addition of in situ generated lithium amides [LiN(H)R] (obtained via an acid-base reaction between n-BuLi and the desired primary amine) into carbodiimides (R-NCN-R) or nitriles (R-CN) has been studied, for the first ti
- Anti?olo, Antonio,Carrillo-Hermosilla, Fernando,Elorriaga, David,García-álvarez, Joaquín,Parra-Cadenas, Blanca
-
supporting information
p. 800 - 812
(2022/02/02)
-
- Photoredox synthesis of functionalized quinazolinesviacopper-catalyzed aerobic oxidative Csp2-H annulation of amidines with terminal alkynes
-
We have developed a visible light-induced photo-redox copper-catalyzed oxidative Csp2-H annulation (Friedel-Crafts-type cyclization) of amidines with terminal alkynes at room temperature to synthesize functionalized quinazolines. We report copp
- Charpe, Vaibhav Pramod,Hwang, Kuo Chu,Ragupathi, Ayyakkannu,Sagadevan, Arunachalam
-
supporting information
p. 5024 - 5030
(2021/07/29)
-
- Synthesis of aminoisoquinolines via Rh-catalyzed [4 + 2] annulation of benzamidamides with vinylene carbonate
-
A new strategy is developed for the synthesis of 1-aminoisoquinoline derivatives. This Rh(III)-catalyzed [4 + 2] annulation reaction employs benzamidines as efficient directing groups and the vinylene carbonate as an acetylene surrogate. Additionally, the reaction features broad substrate scopes and good yields, only producing carbonate anion as byproduct.
- Huang, Xin,Xu, Yingying,Li, Jianglian,Lai, Ruizhi,Luo, Yi,Wang, Qiantao,Yang, Zhongzhen,Wu, Yong
-
supporting information
p. 3518 - 3521
(2021/06/12)
-
- Direct, Late-Stage Mono-N-arylation of Pentamidine: Method Development, Mechanistic Insight, and Expedient Access to Novel Antiparastitics against Diamidine-Resistant Parasites
-
A selective mono-N-arylation strategy of amidines under Chan-Lam conditions is described. During the reaction optimization phase, the isolation of a mononuclear Cu(II) complex provided unique mechanistic insight into the operation of Chan-Lam mono-N-arylation. The scope of the process is demonstrated, and then applied to access the first mono-N-arylated analogues of pentamidine. Sub-micromolar activity against kinetoplastid parasites was observed for several analogues with no cross-resistance in pentamidine and diminazene-resistant trypanosome strains and against Leishmania mexicana. A fluorescent mono-N-arylated pentamidine analogue revealed rapid cellular uptake, accumulating in parasite nuclei and the kinetoplasts. The DNA binding capability of the mono-N-arylated pentamidine series was confirmed by UV-melt measurements using AT-rich DNA. This work highlights the potential to use Chan-Lam mono-N-arylation to develop therapeutic leads against diamidine-resistant trypanosomiasis and leishmaniasis.
- Robertson, Jack,Ungogo, Marzuq A.,Aldfer, Mustafa M.,Lemgruber, Leandro,McWhinnie, Fergus S.,Bode, Bela E.,Jones, Katherine L.,Watson, Allan J. B.,de Koning, Harry P.,Burley, Glenn A.
-
supporting information
p. 3396 - 3401
(2021/09/06)
-
- Construction of a novel asymmetric imidazole-cored AIE probe for ratiometric imaging of endogenous leucine aminopeptidase
-
We report a rational strategy to deliberately construct the first asymmetric tetraarylimidazole-based AIE probe, integrating AIE behavior in synergy with ESIPT character to image endogenous LAP for the first time. It offered good sensitivity and selectivity, and concomitantly, was applied successfully for real-time tracking of LAP in the cisplatin-induced liver injury zebrafish model.
- Huang, Xueyan,Lei, Qian,Huang, Shuai,Zeng, Hongliang,Feng, Bin,Zeng, Qinghai,Hu, Yibo,Zeng, Wenbin
-
supporting information
p. 6608 - 6611
(2021/07/12)
-
- Intramolecular hydrogen bonding stabilizes trans-configuration in a mixed carbene/isocyanide PdII complexes
-
Aromatic amidines 1a-e undergo facile reaction with one isocyanide in PdCl2(CNBut)2 giving carbene complexes 2b-d (Scheme 2) in high isolated yields (79–95%). The structures of 2b–d were confirmed by the 1H and
- Mikhaylov, Vladimir N.,Sorokoumov, Viktor N.,Novikov, Alexander S.,Melnik, Maria V.,Tskhovrebov, Alexander G.,Balova, Irina A.
-
-
- Base-mediated cascade amidination/: N -alkylation of amines by alcohols
-
A base-mediated cascade amidination/N-alkylation reaction of amines by alcohols has been developed. For the first time, nitriles have been identified as an efficient and benign water acceptor reagent in N-alkylation. Notably, the procedure tolerates a series of functional groups, such as methoxyl, halo, vinyl and hetero groups, providing a convenient method to construct different substituted diamino compounds, 15N labeled amine and could be scaled up to 1 mol scale offering 138.7 g of the desired product in good yield in one-pot. Mechanistic studies provided strong evidence for the amidination of amines with nitriles facilitated by t-BuOK.
- Hu, Mao-Lin,Jia, Xiaofei,Liang, Zuyu,Lu, Fenghong,Zhang, Chunyan,Zhang, Guoying
-
supporting information
p. 10489 - 10492
(2020/10/02)
-
- Transition-Metal-Free Synthesis of 1,2-diphenyl-1H-benzo[d] Imidazole Derivatives from N-phenylbenzimidamides and Cyclohexanones
-
A transition-metal-free strategy for the formation of 1,2-diphenyl-1H-benzo[d] imidazoles from N-phenylbenzimidamides and cyclohexanones is introduced. This is the first report on the direct synthesis of 1,2-diphenyl-1H-benzo[d] imidazoles from cyclohexanones and N-phenylbenzimidamides via iodine- promoted oxidative cyclization. Non-aromatic cyclohexanones were smoothly dehydrogenated, and acted as an aryl source using oxygen as a green oxidant. The catalytic use of iodine makes this method quite simple, more economical and convenient. Under optimized conditions, various substituted 1,2-diphenyl-1H-benzo[d] imidazoles were smoothly reacted, and the desired substituted imidazoles were generated with moderate to excellent yields. (Figure presented.).
- Lu, Guoqiang,Luo, Nan,Hu, Fangpeng,Ban, Zihui,Zhan, Zhenzhen,Huang, Guo-Sheng
-
supporting information
p. 487 - 492
(2019/12/12)
-
- Metal-Free Synthesis of Polysubstituted Imidazolinone Through Cyclization of Amidines with 2-Substituted Acrylates
-
Polysubstituted imidazolinones were synthesized in a facile metal-free cascade nucleophilic cyclization of easily available amidines and 2-substituted acrylates. This protocol is distinguished by simple, mild, and catalyst-free reaction conditions with a broad substrate scope, affording the desired products in moderate to good yields and providing an efficient strategy for synthesis of polysubstituted imidazolinone.
- Liu, Zhen,Zhang, Yan-Shun,Wei, Yin,Shi, Min
-
supporting information
p. 1093 - 1099
(2020/02/27)
-
- Base-Mediated Amination of Alcohols Using Amidines
-
Novel and efficient base-mediated N-alkylation and amidation of amidines with alcohols have been developed, which can be carried out in one-pot reaction conditions, which allows for the synthesis of a wide range of N-alkyl amines and free amides in good to excellent yields with high atom economy. In contrast to borrowing hydrogen/hydrogen autotransfer or oxidative-type N-alkylation reactions, in which alcohols are activated by transition-metal-catalyzed or oxidative aerobic dehydrogenation, the use of amidines provides an effective surrogate of amines. This circumvents the inherent necessity in N-alkylation of an oxidant or a catalyst to be stabilized by ligands.
- Chen, Jianbin,Fang, Yanchen,Jia, Xiaofei,Jiang, Shaohua,Li, Zehua,Liang, Zuyu,Lu, Fenghong,Qi, Shuo,Ren, Chaoyu,Yu, Shuangming,Zhang, Chunyan,Zhang, Guoying,Zhang, Sheng
-
p. 7728 - 7738
(2020/07/15)
-
- Synthesis of 1,2-dihydro-1,3,5-triazine derivativesviaCu(ii)-catalyzed C(sp3)-H activation ofN,N-dimethylethanolamine with amidines
-
1,2-Dihydro-1,3,5-triazines and symmetrical 1,3,5-triazines were obtained in up to 81% yields from amidines andN,N-dimethylethanolamine catalyzed by CuCl2. The reaction involves three C-N bond formations during the oxidative annulation process
- Chen, Rener,Ma, Renchao,Ma, Yongmin,Wang, Lei,Wang, Zhiming,Yan, Min
-
supporting information
p. 10946 - 10949
(2020/10/02)
-
- Asymmetric synthesis and biological evaluation of imidazole- and oxazole-containing synthetic lipoxin A4 mimetics (sLXms)
-
Lipoxins (LXs) are endogenously generated eicosanoids with potent bio-actions consistent with attenuation of inflammation. The costly synthesis and metabolic instability of LXs may limit their therapeutic potential. Here we report the synthesis and charac
- de Gaetano, Monica,Butler, Eibhlín,Gahan, Kevin,Zanetti, Andrea,Marai, Mariam,Chen, Jianmin,Cacace, Antonino,Hams, Emily,Maingot, Catherine,McLoughlin, Alisha,Brennan, Eoin,Leroy, Xavier,Loscher, Christine E.,Fallon, Padraic,Perretti, Mauro,Godson, Catherine,Guiry, Patrick J.
-
-
- Method for preparing polysubstituted alkenyl amidine
-
The invention discloses a method for preparing polysubstituted alkenyl amidine. The structural formula of the polysubstituted alkenyl amidine is shown in a formula I. The preparation method comprisesthe following steps: carrying out C-H activation/C-C for
- -
-
Paragraph 0040-0044
(2019/06/27)
-
- Eco-friendly Synthesis of 3-(Aryl)-2,6-diphenylpyrimidin-4(3H)-ones, Ethyl-1-(aryl)-1,6-dihydro-2-(aryl)-6-oxopyrimidine-4-carboxylates and 6-(4-Arylphenyl)-2-isopropylpyrimidin-4(3H)-one
-
In present communication, we report the synthesis of pyrimidin-4(3H)-one derivatives by microwave irradiation in good yields and less reaction time. All titled compounds were characterized by IR, NMR and Mass spectral analyses.
- Anantoju, Kishore Kumar,Eppakayala, Laxminarayana,Maringanti, Thirumala Chary
-
p. 845 - 850
(2019/03/07)
-
- Acid-catalyzed synthesis of imidazole derivatives via N-phenylbenzimidamides and sulfoxonium ylides cyclization
-
A straightforward method to synthesize imidazole derivatives from amidines and sulfoxonium ylides catalyzed by acids is reported in this study. Specifically, catalyzed by trifluoroacetic acid in DCE solvents can improve synthesis efficiency under metal-fr
- Tian, Yuan,Qin, Mingda,Yang, Xueying,Zhang, Xueguo,Liu, Yafeng,Guo, Xin,Chen, Baohua
-
supporting information
p. 2817 - 2823
(2019/04/13)
-
- Metal-Free C-B Bond Cleavage: An Acid Catalyzed Three-Component Reaction Construction of Imidazole-Containing Triarylmethanes
-
An efficient acid-catalyzed strategy to prepare imidazole-containing triarylmethanes from amidines, ynals, and boronic acids has been developed. It represents an unprecedented and novel metal-free C-B bond cleavage strategy as a workable route to form new carbon-carbon bonds.
- Wang, Changcheng,Yu, Yue,Su, Zhengquan,Li, Xuechen,Cao, Hua
-
supporting information
p. 4420 - 4423
(2019/06/27)
-
- Transition-metal-free three-component reaction: Additive controlled synthesis of sulfonylated imidazoles
-
Two efficient transition-metal-free highly regioselective pathways for constructing sulfonylated imidazoles via three-component reactions of amidines, ynals, and sodium sulfonates have been developed. The generations of different sulfonylated imidazoles w
- Liu, Wei,Zhang, Yu,He, Jiaming,Yu, Yue,Yuan, Jiajun,Ye, Xiaoyi,Zhang, Ziwu,Xue, Liang,Cao, Hua
-
p. 11348 - 11358
(2019/09/09)
-
- Rhodium-catalyzed C-H activation/annulation of amidines with 4-diazoisochroman-3-imines toward isochromeno[3,4-: C] isoquinolines
-
A rhodium-catalyzed C-H activation/annulation of amidines with 4-diazoisochroman-3-imines has been established to afford a series of 8-amino-5H-isochromeno[3,4-c]isoquinolines in moderate to good yields with good functional group tolerance. This reaction
- Xu, Shengbo,Qiao, Shanshan,Sun, Song,Yu, Jin-Tao,Cheng, Jiang
-
p. 8417 - 8424
(2019/09/30)
-
- Arylamidine compounds and synthetic method thereof
-
The invention provides a synthetic method for arylamidine compounds. With the synthetic method provided by the invention, arylamidine is prepared by using aniline and benzonitrile as raw materials through a series of reactions; arylamidine compounds 4A to
- -
-
Paragraph 0176; 0178; 0341; 0343; 0349; 0351
(2019/11/20)
-
- -Cycloaddition of 2 H-Azirines with Nitrosoarenes: Visible-Light-Promoted Synthesis of 2,5-Dihydro-1,2,4-oxadiazoles
-
A formal [3 + 2]-cycloaddition reaction of 2H-azirines with nitrosoarenes has been achieved under irradiation by visible light with the assistance of organic dye photoredox catalyst. This method utilizes nitrosoarenes as efficient radical acceptors and pr
- Cai, Bao-Gui,Chen, Ze-Le,Xu, Guo-Yong,Xuan, Jun,Xiao, Wen-Jing
-
-
- Unaromatized Tetrahydrobenzimidazole Synthesis from p-Benzoquinone and N-Arylamidines and their Cytotoxic Potential
-
A diverse set of unaromatized and densely functionalized tetrahydrobenzimidazole adducts were obtained in good yields by simple mixing p-benzoquinone 1 with N-arylamidines 2 under mild conditions. The main features of these adducts include a hemi N,O-acet
- Tran, Minh Quan,Nguyen, Thanh Binh,Sawadogo, Wamtinga Richard,Ermolenko, Ludmila,Song, Sungmi,Retailleau, Pascal,Diederich, Marc,Al-Mourabit, Ali
-
supporting information
p. 5878 - 5884
(2018/10/09)
-
- HETEROCYCLIC LIPXON ANALOGS AND USES THEROF
-
The present invention relates to a compound of formula (I): wherein L is an optionally substituted heterocyclic group excluding unsubstituted monocyclic pyridine groups; wherein a is 0, 1 or 2; wherein R1 is H or with R2 is a bond; wherein R2 is an optionally substituted alkoxy or aryloxy group, or with R1 forms a bond; wherein R3 is an optionally substituted alkyl group; and wherein R4 is CH2, CMe2 or O. Such compounds may be used in the treatment or prophylaxis of a disease or condition in which inhibition of acute inflammation and/or promotion of its resolution and/or suppression of fibrosis.
- -
-
Page/Page column 83
(2018/03/09)
-
- N-Heterocyclic carbene-catalyzed annulation of ynals with amidines: Access to 1,2,6-trisubstituted pyrimidin-4-ones
-
An N-heterocyclic carbene-catalyzed annulation of ynals and amidines has been reported to construct pyrimidin-4-ones. The protocol features a broad substrate scope and mild conditions. Furthermore, an oxidative strategy to catalytically generate ynal-deri
- Xie, Yangxi,Wang, Jian
-
p. 4597 - 4600
(2018/05/14)
-
- 1,1-Diphosphines and divinylphosphines via base catalyzed hydrophosphination
-
A catalytic hydrophosphination route to 1,1-diphosphines is yet to be reported: these narrow bite angle pro-ligands have been used to great effect as ligands in homogeneous catalysis. We herein demonstrate that terminal alkynes readily undergo double hydrophosphination with HPPh2 and catalytic potassium hexamethyldisilazane (KHMDS) to generate 1,1-diphosphines. A change to H2PPh leads to the formation of P,P-divinyl phosphines.
- Coles,Mahon,Webster
-
supporting information
p. 10443 - 10446
(2018/09/21)
-
- Intramolecular alkene hydroamination and degradation of amidines: Divergent behavior of rare earth metal amidinate intermediates
-
Direct N-H addition of amidines to alkenes is a highly valuable but challenging transformation that remains elusive. Now, the intramolecular hydroamidination of N-alkenylamidines is achieved by using a rare earth catalyst, which provides an efficient and atom-economical approach for substituted imidazolines and tetrahydropyrimidines. Moreover, a mild and efficient method for the catalytic degradation of amidines to give amines and nitriles is also developed. Additionally, amidine reconstruction followed by an intramolecular alkene hydroamidination strategy for the synthesis of substituted imidazolines and tetrahydropyrimidines from secondary enamines and inactive amidines has also been established, which may circumvent the need for some unavailable starting materials. The mechanistic studies prove that these reactions proceed via a key lanthanide amidinate intermediate that can undergo substrate- and amine-controlled chemodivergent transformations: intramolecular alkene insertion, nitrile extrusion, amidinate reconstruction, or a combination of the reactions. The results presented here not only demonstrate the synthetic potential and versatility of alkene hydroamidination with substrates, but also provide a good insight into the factors that promote or deter the hydroamidination of alkenes.
- Zhang, Dexing,Liu, Ruiting,Zhou, Xigeng
-
p. 5573 - 5581
(2018/11/20)
-
- Vanadium-Catalyzed Oxidative C(CO)-C(CO) Bond Cleavage for C-N Bond Formation: One-Pot Domino Transformation of 1,2-Diketones and Amidines into Imides and Amides
-
A novel vanadium-catalyzed one-pot domino reaction of 1,2-diketones with amidines has been identified that enables their transformation into imides and amides. The reaction proceeds by dual acylation of amidines via oxidative C(CO)-C(CO) bond cleavage of 1,2-diketones to afford N,N′-diaroyl-N-arylbenzamidine intermediates. In the reaction, these intermediates are easily hydrolyzed into imides and amides through vanadium catalysis. This method provides a practical, simple, and mild synthetic approach to access a variety of imides as well as amides in high yields. Moreover, one-step construction of imide and amide bonds with a long-chain alkyl group is an attractive feature of this protocol.
- Digwal, Chander Singh,Yadav, Upasana,Ramya, P. V. Sri,Sana, Sravani,Swain, Baijayantimala,Kamal, Ahmed
-
p. 7332 - 7345
(2017/07/26)
-
- Silver-catalyzed [3 + 2] domino reaction: An efficient strategy to synthesize imidazole-5-carbaldehydes
-
An unprecedented regioselective silver-catalyzed [3 + 2] domino reaction of amidines and ynals for the formation of C-N bonds has been developed. The reaction provided a new route to prepare imidazole-5-carbaldehydes which are important intermediates for the construction of fine chemicals. The reaction proceeds smoothly with a broad range of substrates to give imidazoles in good yields.
- Wang, Changcheng,Jiang, Hangqi,Chen, Weifeng,Dong, Jun,Chen, Zhengwang,Cao, Hua
-
supporting information
p. 6463 - 6466
(2017/08/16)
-
- Substrate-Controlled Selectivity Switch in a Three-Component Reaction: A Ag-Catalyzed Strategy for the Synthesis of Functionalized Imidazoles
-
An efficient Ag-catalyzed three-component reaction of amidines, ynals, and alcohols, phenols, or water has been developed. This strategy provides a wide range of substrates and represents a simple process for the preparation of different imidazole derivatives in good yields with high regioselectivities.
- Wang, Changcheng,Wang, Enming,Chen, Weixin,Zhang, Lijuan,Zhan, Haiying,Wu, Yuanheng,Cao, Hua
-
p. 9144 - 9153
(2017/09/11)
-
- Copper-Catalyzed Intramolecular C-H Amination: A New Entry to Substituted Xanthine Derivatives
-
Catalytic synthesis of xanthines was achieved in the presence of a copper catalyst. The process involves copper-catalyzed intramolecular C-H amination of benzamidines that possess a uracil moiety and produces variously substituted xanthines generally in good to high yields. This work introduces a new, facile approach to polysubstituted xanthine compounds..
- Shimizu, Maki,Hayama, Noboru,Kimachi, Tetsutaro,Inamoto, Kiyofumi
-
p. 4183 - 4190
(2017/09/12)
-
- Iodine-Mediated Aryl C?H Amination for the Synthesis of Benzimidazoles and Pyrido[1,2-a]benzimidazoles
-
An intramolecular aryl C?H amination reaction has been achieved using molecular iodine as the sole oxidant for the synthesis of benzimidazole derivatives. The required substrates were readily prepared by addition or coupling of arylamines with the corresponding nitriles or aryl iodides. Iodine-mediated oxidative cyclization of these substrates in the presence of potassium carbonate (K2CO3) as base afforded the corresponding products in moderate to good yields. The transition metal-free protocol presented here is insensitive to air and operationally simple. This versatile and eco-friendly synthetic methodology is broadly applicable to a variety of N-aryl-substituted amidines and pyridin-2-amines, and provides direct access to both 1H-benzo[d]imidazole and pyrido[1,2-a]benzimidazole derivatives from the corresponding precursors. (Figure presented.).
- Lv, Zhigang,Liu, Jing,Wei, Wei,Wu, Jie,Yu, Wenquan,Chang, Junbiao
-
supporting information
p. 2759 - 2766
(2016/09/13)
-
- Sulfated tungstate catalyzed activation of nitriles: addition of amines to nitriles for synthesis of amidines
-
An efficient and mild method for the synthesis of amidines by direct nucleophilic addition of amines to nitriles using sulfated tungstate as heterogeneous catalyst is described. Highlight of the method is its applicability for the synthesis of amidines using a wide variety of amines including ammonia as ammonium acetate and nitriles. Catalyst is mildly acidic, stable, easy to prepare and separate from the reaction mass.
- Veer, Sachin D.,Katkar, Kamlesh V.,Akamanchi, Krishnacharya G.
-
supporting information
p. 4039 - 4043
(2016/08/18)
-
- Direct Access to 1,3,5-Trisubstituted 1 H -1,2,4-Triazoles from N -Phenylbenzamidines via Copper-Catalyzed Diamination of Aryl Nitriles
-
A copper-catalyzed formation of C-N/N-N bonds using N-phenylbenzamidines with aryl nitriles has been developed and affords a route to 1,3,5-trisubstituted 1H-1,2,4-triazoles in moderate to excellent yields. The method is operationally simple and environme
- Zhang, Lutao,Tang, Dong,Gao, Jing,Wang, Jing,Wu, Ping,Meng, Xu,Chen, Baohua
-
p. 3924 - 3930
(2016/11/11)
-
- A new more atom-efficient multi-component approach to tetrasubstituted imidazoles: One-pot condensation of nitriles, amines and benzoin
-
A new more atom-efficient multi-component approach for the synthesis of tetrasubstituted imidazoles via the one-pot condensation of nitriles, primary amines and benzoin has been described. Using this method, a wide range of structurally diverse nitriles and primary amines were successfully condensed with benzoin in glycerol in the presence of TFA under microwave irradiation at 120 °C and all the products were obtained in good to excellent yields with higher atom efficiencies in comparison with the commonly used four-component condensation of aldehydes, ammonium acetate, primary amines and benzil.
- Khalafi-Nezhad, Ali,Shekouhy, Mohsen,Sharghi, Hashem,Aboonajmi, Jasem,Zare, Abdolkarim
-
p. 67281 - 67289
(2016/07/30)
-
- Synthesis of Oxadiazol-5-imines via the Cyclizative Capture of in Situ Generated Cyanamide Ions and Nitrile Oxides
-
An unprecedented intermolecular cyclizative capture of the cyanamide anion and several nitrile oxides enables the synthesis of oxadiazol-5-imines.
- Bhat, Shreesha V.,Robinson, David,Moses, John E.,Sharma, Pallavi
-
p. 1100 - 1103
(2016/03/15)
-
- Synthesis of substituted imidazopyridines from perfluorinated pyridine derivatives
-
4-Phenylsulfonyl tetrafluoropyridine was reacted with various N-aryl amidines to give the corresponding imidazopyridine systems via an intramolecular nucleophilic aromatic substitution process whilst pentafluoropyridine gave N′-(perfluoropyridin-4-yl)-N-p
- Poorfreidoni, Alireza,Ranjbar-Karimi, Reza
-
p. 5781 - 5783
(2016/12/06)
-
- Investigating Scale-Up and Further Applications of DABAL-Me3 Promoted Amide Synthesis
-
Methods for the batch scale up of DABAL-Me3 promoted direct ester to amide synthesis have been demonstrated at 10-100 g scales using a tert-amide model compound. Procedures for 20 g scale couplings in standard laboratory glassware and up to 0.1 kg in industry-standard jacketed glass reactors in near quantitative yields are given. A derivative of the anticancer agent Imatinib (Gleevec) has been synthesized on a 26 g scale (98% yield, >98% purity) establishing DABAL-Me3 as a potential alternative for the synthesis of amides in API scale preparations. Continuous flow methodology provides a method for larger scales (productivities of >50 g h-1). In addition, nitriles were coupled to primary amines and hydrazines with DABAL-Me3, resulting in the clean formation of free amidines (16 examples) and amidrazones.
- Lee, Darren S.,Amara, Zacharias,Poliakoff, Martyn,Harman, Thomas,Reid, Gary,Rhodes, Barrie,Brough, Steve,McInally, Thomas,Woodward, Simon
-
p. 831 - 840
(2015/07/27)
-
- Synthesis of secondary amides from N-Substituted amidines by tandem oxidative rearrangement and isocyanate elimination
-
In this work an efficient tandem process transforming N-substituted amidines into secondary amides has been described. The process involves N-acylurea formation by reaction of the substrate with bis(acyloxy)(phenyl)-λ3-iodane followed by isocyanate elimination. The periodinane reagents are obtained from the commercially available phenyl-iodine(III) diacetate [PhI(OAc)2, (PIDA)] by ligand exchange with carboxylic acids. The N-substituted amidine substrates are easily synthesized from readily available nitriles. The method is applicable for secondary amide synthesis, based on both aliphatic and (hetero)aromatic amines, including challenging amides consisting of sterically hindered acids and amines. Moreover, the protocol allows one to combine steric bulk with electron deficiency in the target amides (aniline based). Such compounds are difficult to synthesize efficiently based on classical condensation reactions involving carboxylic acids and amines. Overall, the synthetic protocol transforms a nitrile into a secondary amide in both aliphatic and (hetero)aromatic systems.
- Debnath, Pradip,Baeten, Mattijs,Lefvre, Nicolas,Van Daele, Stijn,Maes, Bert U. W.
-
supporting information
p. 197 - 209
(2015/03/03)
-
- Acyclic aminocarbene-like palladium complex-catalyzed Suzuki-Miyaura reaction at low catalyst loadings
-
A series of air-stable aminocarbene-like palladium(II) complexes were easily prepared by the reaction of bis-aromaticisocyanide-dichloropalladium(II) with N-arylbenzamidines. 0.1 mol % of the optimal palladium complex 3a showed excellent catalytic activity for Suzuki-Miyaura cross-coupling reaction at room temperature and the desired products were isolated in up to 98% yields. Moreover, a large-scale reaction showed that 0.01 mol % 3a was enough to catalyze the coupling reaction efficiently at room temperature to give the desired product in 93% yield.
- Fang, Yi,Wang, Shun-Yi,Ji, Shun-Jun
-
supporting information
p. 9679 - 9683
(2015/12/04)
-
- Facile N-arylation of amidines and N,N-disubstituted amidines
-
A metal-free method for the N-arylation of amidines and N,N-disubstituted amidines using o-silylaryl triflate under very mild reaction conditions is developed. The reactions are compatible with a variety of functional groups. Imines can also be N-arylated by this method. Preparation of substituted phenanthridines via a Pd catalyzed intramolecular cyclization of the iodine containing N-arylation product is demonstrated.
- Yao, Tuanli
-
supporting information
p. 4623 - 4626
(2015/07/08)
-
- Synthesis of 2-arylquinazolin-4(3H)-ones by N-aryl benzamidines with aromatic carbonates
-
The reaction of N-aryl benzamidines 1a, 1b, 1c, 1d, 1e, 1f, 1g, 1h, 1i, 1j, 1k, 1l, 1m, 1n with diphenyl carbonate 2a or ethyl phenyl carbonate 2b synthesized 2-arylquinazolin-4(3H)-ones 3a, 3b, 3c, 3d, 3e, 3f, 3g, 3h, 3i, 3j, 3k, 3l, 3m, 3n in simple and
- Aikawa, Shunichi,Sekiguchi, Chiharu,Yamazaki, Yuko,Hattori, Mika,Isaka, Tatsuya,Yoshida, Yasuhiko,Ihara, Shogo
-
p. 343 - 348
(2014/04/17)
-
- Copper-catalyzed three-component synthesis of 3-Aminopyrazoles and 4-iminopyrimidines via β-alkynyl-N-sulfonyl ketenimine intermediates
-
3-Aminopyrazoles and 4-iminopyrimidines were efficiently prepared via copper-catalyzed three-component reactions of butadiynes, sulfonylazides, and hydrazides or imidamides. The reactions were regioselectively approached via the formation of a β-alkynyl-N-sulfonyl ketenimine intermediate which represented a new and effective 1,3-dielectrophilic equivalent in organic synthesis.
- Xing, Yanpeng,Cheng, Binyu,Wang, Jing,Lu, Ping,Wang, Yanguang
-
supporting information
p. 4814 - 4817
(2015/04/27)
-
- Copper-catalyzed domino reaction between 1-(2-halophenyl)methanamines and amidines or imidates for the synthesis of 2-substituted quinazolines
-
The CuI-catalyzed domino reaction between 1-(2-bromophenyl)methanamines and amidines using K3PO4 as the base, pivalic acid as the additive, and aerial oxygen as the oxidant gives access to substituted quinazolines in a single step wi
- Omar, Mohamed A.,Conrad, Jürgen,Beifuss, Uwe
-
p. 3061 - 3072
(2014/04/17)
-
- Trimethylaluminium-mediated reaction of primary carboxamides with amines and indoles: A convenient synthesis of amidines and indole-3-acylimines
-
A simple, convenient and general method, exhibiting good functional group tolerance, is described for the synthesis of N- and N,N-disubstituted amidines by the reaction of primary carboxamides with amines mediated by trimethylaluminium (AlMe3).
- Velavan,Sumathi,Balasubramanian
-
p. 5806 - 5815
(2014/10/16)
-
- Copper-catalyzed oxidative diamination of terminal alkynes by amidines: Synthesis of 1,2,4-trisubstituted imidazoles
-
An efficient copper-catalyzed synthesis of 1,2,4-trisubstituted imidazoles using amidines and terminal alkynes has been developed. Overall, the oxidative process, which involves Na2CO3, pyridine, a catalytic amount of CuCl2/sub
- Li, Jihui,Neuville, Luc
-
supporting information
p. 1752 - 1755
(2013/06/26)
-
- C-H cycloamination of N-aryl-2-aminopyridines and N-arylamidines catalyzed by an in situ generated hypervalent iodine(iii) reagent
-
A metal-free synthesis of diversified pyrido[1,2-a]benzimidazoles and 1H-benzo[d]imidazoles from N-aryl-2-aminopyridines and N-arylamidines has been developed. The C-H cycloamination reaction was catalyzed by hypervalent iodine(iii) species generated in situ from iodobenzene (catalytic) and peracetic acid (stoichiometric). The reaction proceeded smoothly at ambient temperature to provide the corresponding N-heterocycles in good to excellent yields.
- He, Yimiao,Huang, Jinbo,Liang, Dongdong,Liu, Lanying,Zhu, Qiang
-
supporting information
p. 7352 - 7354
(2013/09/23)
-
- Nitrenic reactivity of diazirines
-
Butyl 3-bromo-3H-diazirine-3-carboxylate (7) and 3-bromo-3-phenyl-3H- diazirine (17) exhibit nitrenic reactivity with phenylmagnesium bromide or tetrabutylammonium cyanide. The formation of several N,N′-disubstituted amidines is attributed to the intermediacy of 1-phenyl or 1-cyano-1H-diazirines possessing a singlet imidoylnitrene character at the N2 atom. Most notably, the reaction of 7 with PhMgBr in diethyl ether affords 2-hydroxy-2,2,N- triphenylacetamidine (9) and 2-methyl-5,5-diphenyl-4-phenylamino-2,5- dihydrooxazole (10) as products derived from nitrene insertion to the ether α-C-H bond.
- Kolá?ová, Petra,?molík, Václav,Linhart, Igor,Martínez, Ignacio álvarez,Martin?, Tomá?
-
p. 6764 - 6767
(2013/11/19)
-