- A method for synthesizing compounds with amide bonds
-
The present invention discloses a method for synthesizing a compound having an amide bond, the synthesis method of the compound having an amide bond comprises the following steps: step 1, in an anhydrous environment, a strong alkaline accelerator, an amine compound and an ester compound are added to the reaction tube in turn, stirred to make the reaction occur; step 2, after the end of the reaction, water is added to it to quench the reaction, and the solid precipitated to obtain a compound with an amide bond is precipitated. The synthesis method provided by the present invention enables the simple and efficient synthesis of compounds having amide bonds, effectively reducing by-products and improving yield.
- -
-
Paragraph 0204-0210
(2022/04/08)
-
- Zirconium Oxide-Catalyzed Direct Amidation of Unactivated Esters under Continuous-Flow Conditions
-
A sustainable and environmentally benign direct amidation reaction of unactivated esters with amines has been developed in a continuous-flow system. A commercially available amorphous zirconium oxide was found to be an efficient catalyst for this reaction. While the typical amidation of esters with amines requires a stoichiometric amount of a promoter or metal activator, the present continuous-flow method enabled the direct amidation reaction under additive-free conditions with an extensive diversity towards various functional groups. High yields of the products were obtained with a nearly equimolar proportion of starting materials to reduce byproduct formation, which renders this process applicable for use in a sequential-flow system. (Figure presented.).
- Rashed, Md. Nurnobi,Masuda, Koichiro,Ichitsuka, Tomohiro,Koumura, Nagatoshi,Sato, Kazuhiko,Kobayashi, Shū
-
p. 2529 - 2535
(2021/02/01)
-
- A practical and sustainable protocol for direct amidation of unactivated esters under transition-metal-free and solvent-free conditions
-
In this paper, a NaOtBu-mediated synthesis approach was developed for direct amidation of unactivated esters with amines under transition-metal-free and solvent-free conditions, affording a series of amides in good to excellent yields at room temperature. In particular, an environmentally friendly and practical workup procedure, which circumvents the use of organic solvents and chromatography in most cases, was disclosed. Moreover, the gram-scale production of representative products3a,3wand3auwas efficiently realized by applying operationally simple, sustainable and practical procedures. Furthermore, this approach was also applicable to the synthesis of valuable molecules such as moclobemide (a powerful antidepressant), benodanil and fenfuram (two commercial agricultural fungicides). These results demonstrate that this protocol has the potential to streamline amide synthesis in industry. Meanwhile, quantitative green metrics of all the target products were evaluated, implying that the present protocol is advantageous over the reported ones in terms of environmental friendliness and sustainability. Finally, additional experiments and computational calculations were carried out to elucidate the mechanistic insight of this transformation, and one plausible mechanism was provided on the basis of these results and the related literature reports.
- Chen, Cheng,Cheng, Hua,Du, Min-Chen,Qian, Liang,Qin, Xin,Sang, Wei,Yao, Wei-Zhong,Yuan, Ye,Zhang, Rui
-
supporting information
p. 3972 - 3982
(2021/06/17)
-
- UV-Light-Induced N-Acylation of Amines with α-Diketones
-
Herein, we develop a mild method for N-acylation of primary and secondary amines with α-diketones induced by ultraviolet (UV) light. Forty-six examples with various functional groups are explored at room temperature with irradiation by three 26 W UV lamps (350-380 nm). The yield reaches 97%. The gram scale experiment product yield is 76%. Moreover, this system can be applied to the synthesis of several amino acid derivatives. Mechanistic studies show that benzoin is generated in situ from benzil under UV irradiation.
- Xu, Zhihui,Yang, Tianbao,Tang, Niu,Ou, Yifeng,Yin, Shuang-Feng,Kambe, Nobuaki,Qiu, Renhua
-
supporting information
p. 5329 - 5333
(2021/07/21)
-
- Dehydrogenative amide synthesis from alcohols and amines utilizing N-heterocyclic carbene-based ruthenium complexes as efficient catalysts: The influence of catalyst loadings, ancillary and added ligands
-
The metal-catalyzed dehydrogenative coupling of alcohols and amines to access amides has been recognized as an atom-economic and environmental-friendly process. Apart from the formation of the amide products, three other kinds of compounds (esters, imines and amines) may also be produced. Therefore, it is of vital importance to investigate product distribution in this transformation. Herein, N-heterocyclic carbene-based Ru (NHC/Ru) complexes [Ru-1]-[Ru-5] with different ancillary ligands were prepared and characterized. Based on these complexes, we selected condition A (without an added NHC precursor) and condition B (with an added NHC precursor) to comprehensively explore the selectivity and yield of the desired amides. After careful evaluation of various parameters, the Ru loadings, added NHC precursors and the electronic/steric properties of ancillary NHC ligands were found to have considerable influence on this catalytic process.
- Wang, Wan-Qiang,Wang, Zhi-Qin,Sang, Wei,Zhang, Rui,Cheng, Hua,Chen, Cheng,Peng, Da-Yong
-
-
- Microwave-assisted catalytic method for a green synthesis of amides directly from amines and carboxylic acids
-
Amide bonds are among the most interesting and abundant molecules of life and products of the chemical pharmaceutical industry. In this work, we describe a method of the direct synthesis of amides from carboxylic acids and amines under solvent-free conditions using minute quantities of ceric ammonium nitrate (CAN) as a catalyst. The reactions are carried out in an open microwave reactor and allow the corresponding amides to be obtained in a fast and effective manner when compared to other procedures of the direct synthesis of amides from acids and amines reported so far in the literature. The amide product isolation procedure is simple, environmentally friendly, and is performed with no need for chromatographic purification of secondary amides due to high yields. In this report, primary amines were used in most examples. However, the developed procedure seems to be applicable for secondary amines as well. The methodology produces a limited amount of wastes, and a catalyst can be easily separated. This highly efficient, robust, rapid, solvent-free, and additional reagent-free method provides a major advancement in the development of an ideal green protocol for amide bond formation.
- Kolanowski, Jacek L.,Markiewicz, Wojciech T.,Zarecki, Adam P.
-
supporting information
(2020/04/23)
-
- Tris(o-phenylenedioxy)cyclotriphosphazene as a Promoter for the Formation of Amide Bonds between Aromatic Acids and Amines
-
The atom-efficient formation of amide bonds has emerged as a top-priority research field in organic synthesis, as amide bonds constitute the backbones of proteins and represent an important structural motif in drug molecules. Currently, the increasing demand for novel discoveries in this field has focused substantial attention on this challenging subject. Herein, the degradable 1,3,5-triazo-2,4,6-triphosphorine (TAP) motif is presented as a new condensation system for the dehydrative formation of amide bonds between diverse combinations of aromatic carboxylic acids and amines. The underlying reaction mechanism was investigated, and potential catalyst intermediates were characterized using 31 P NMR spectroscopy and ESI mass spectrometry.
- Movahed, Farzaneh Soleymani,Sawant, Dinesh N.,Bagal, Dattatraya B.,Saito, Susumu
-
p. 3253 - 3262
(2020/11/02)
-
- Well-defined N-heterocyclic carbene/ruthenium complexes for the alcohol amidation with amines: The dual role of cesium carbonate and improved activities applying an added ligand
-
Dehydrogenative amide bond formation from alcohols and amines has been regarded as an atom-economic and sustainable process. Among various catalytic systems, N-heterocyclic carbene (NHC)-based Ru catalytic systems have attracted growing interest due to the outstanding properties of NHCs as ligands. Herein, an NHC/Ru complex (1) was prepared and its structure was further confirmed with X-ray crystallography. In the presence of Cs2CO3, two NHC/Ru-based catalytic systems were disclosed to be active for this amide synthesis. System A, which did not contain any added ligand, required a catalyst loading of 1.00 mol%. Interestingly, improved catalytic performance was realized by the addition of an NHC precursor (L). Optimization of the amounts of L and other conditions gave rise to system B, a much more potent system with the Ru loading as low as 0.25 mol%. Moreover, an NHC-Ru-carbonate complex 6 was identified from the refluxing toluene of 1 and Cs2CO3, and further investigations revealed that 6 was an important intermediate for this catalytic reaction. Based on the above results, we claimed that the role of Cs2CO3 was to facilitate the formation of key intermediate 6. On the other hand, it provided the optimized basicity for the selective amide formation.
- Wang, Wan-Qiang,Yuan, Ye,Miao, Yang,Yu, Bao-Yi,Wang, Hua-Jing,Wang, Zhi-Qin,Sang, Wei,Chen, Cheng,Verpoort, Francis
-
-
- Clickable coupling of carboxylic acids and amines at room temperature mediated by SO2F2: A significant breakthrough for the construction of amides and peptide linkages
-
The construction of amide bonds and peptide linkages is one of the most fundamental transformations in all life processes and organic synthesis. The synthesis of structurally ubiquitous amide motifs is essential in the assembly of numerous important molecules such as peptides, proteins, alkaloids, pharmaceutical agents, polymers, ligands and agrochemicals. A method of SO2F2-mediated direct clickable coupling of carboxylic acids with amines was developed for the synthesis of a broad scope of amides in a simple, mild, highly efficient, robust and practical manner (>110 examples, >90% yields in most cases). The direct click reactions of acids and amines on a gram scale are also demonstrated using an extremely easy work-up and purification process of washing with 1 M aqueous HCl to provide the desired amides in greater than 99% purity and excellent yields.
- Wang, Shi-Meng,Zhao, Chuang,Zhang, Xu,Qin, Hua-Li
-
p. 4087 - 4101
(2019/04/30)
-
- An open-source approach to automation in organic synthesis: The flow chemical formation of benzamides using an inline liquid-liquid extraction system and a homemade 3-axis autosampling/product-collection device
-
Several open-source hardware and software technologies (RAMPS, Python, PySerial, OpenCV) were used to control an automated flow chemical synthesis system. The system was used to effect the synthesis of a series of benzamides. An inexpensive Raspberry Pi single board computer provided an electronic interface between the control computer and the RAMPS motor driver boards.
- O'Brien, Matthew,Hall, April,Schrauwen, John,van der Made, Joyce
-
supporting information
p. 3152 - 3157
(2018/03/21)
-
- Efficient N-Heterocyclic Carbene/Ruthenium Catalytic Systems for the Alcohol Amidation with Amines: Involvement of Poly-Carbene Complexes?
-
The atom-economic direct amidation of alcohols with amines has been recently highlighted as an attractive and promising transformation. Among the versatile reported catalytic systems, in situ generated N-heterocyclic carbene (NHC)/ruthenium (Ru) catalytic systems have demonstrated their advantages such as easy operation and use of commercial Ru compounds. However, the existing catalyst loadings are relatively high, and additional insights for the in situ catalyst generation are still not well-documented. In this work, a variety of benzimidazole-based NHC precursors were initially synthesized. Through the screening of various NHC precursors and other reaction conditions, active in situ catalytic systems were discovered for the efficient amide synthesis. Notably, the catalyst loading is as low as 0.5 mol %. Furthermore, additional experiments were performed to validate the rationale for the superiority of the current catalytic systems over our previous system. It was observed that the ligand structure is one of the reasons for the higher activity. In addition, the higher ratio of the NHC precursor/[Ru] is another important factor for the improvement. Further HR-MS analysis identified the formation of two mono-NHC-Ru species as major species and two Ru species bearing multiple NHC ligands as minor species. Hopefully, the efficient and readily-accessible catalytic systems reported herein could demonstrate great potential for further practical applications.
- Cheng, Hua,Xiong, Mao-Qian,Zhang, Ni,Wang, Hua-Jing,Miao, Yang,Su, Wei,Yuan, Ye,Chen, Cheng,Verpoort, Francis
-
p. 4338 - 4345
(2018/09/06)
-
- In situ Generated Ruthenium Catalyst Systems Bearing Diverse N-Heterocyclic Carbene Precursors for Atom-Economic Amide Synthesis from Alcohols and Amines
-
The transition-metal-catalyzed direct synthesis of amides from alcohols and amines is herein demonstrated as a highly environmentally benign and atom-economic process. Among various catalyst systems, in situ generated N-heterocyclic carbene (NHC)-based ruthenium (Ru) halide catalyst systems have been proven to be active for this transformation. However, these existing catalyst systems usually require an additional ligand to achieve satisfactory results. In this work, through extensive screening of a diverse variety of NHC precursors, we discovered an active in situ catalyst system for efficient amide synthesis without any additional ligand. Notably, this catalyst system was found to be insensitive to the electronic effects of the substrates, and various electron-deficient substrates, which were not highly reactive with our previous catalyst systems, could be employed to afford the corresponding amides efficiently. Furthermore, mechanistic investigations were performed to provide a rationale for the high activity of the optimized catalyst system. NMR-scale reactions indicated that the rapid formation of a Ru hydride intermediate (signal at δ=?7.8 ppm in the 1H NMR spectrum) after the addition of the alcohol substrate should be pivotal in establishing the high catalyst activity. Besides, HRMS analysis provided possible structures of the in situ generated catalyst system.
- Cheng, Hua,Xiong, Mao-Qian,Cheng, Chuan-Xiang,Wang, Hua-Jing,Lu, Qiang,Liu, Hong-Fu,Yao, Fu-Bin,Chen, Cheng,Verpoort, Francis
-
p. 440 - 448
(2018/02/06)
-
- A study on reactions of an alkynylsilane with oxone-KX (X = Cl, Br, I) and its one-pot transformation into an amide/ester
-
Oxyhalogenation reactions of a variety of alkynylsilanes were studied using oxone as mild oxidant and KCl, KBr, and KI as halogen sources. In this study, reaction of an alkynylsilane with oxone-KX (X = Cl or Br) produced trichloromethyl/tribromomethyl ketones inhigh yields. Under similar conditions, however, reactions of alkynylsilanes with oxone-KI were found to give exclusively 1,2,2-triiodovinyl derivatives in high yields. In this study, new methods were deveoped for effcient one-pot tranformation of alkynylsilanes into amides and esters by reaction with amines and alcohols respectively via trihalomethyl ketone.
- Sriramoju, Vinodkumar,Jillella, Raveendra,Kurva, Srinivas,Madabhushi, Sridhar
-
supporting information
p. 560 - 562
(2017/03/30)
-
- A process for preparing N - alkyl amide method (by machine translation)
-
The invention discloses a method for preparing N - alkyl amide of the method. In the reaction container, joins the nitrile, oxime, transition metal catalyst iridium complex [Cp * IrCl2 ]2 , Toluene; the reaction mixture in 100 °C reaction under 6 hours, cooling to room temperature; then the alcohol and alkali compound is added, the reaction mixture in the 130 °C react again under 12 hours later, then through the column separation, to obtain the target compound. The invention from the fully commercialized nitrile, proceed wowo and mellow, in the participation of transition metal iridium catalyst, to directly obtain N - alkyl amide, the reaction exhibits three significant advantages: 1) the use of the commercialization of the starting material; 2) low catalyst load; 3) is environment-friendly and easy to control. Therefore, the reaction in accordance with the requirement of green chemistry, has broad prospects of development. (by machine translation)
- -
-
Paragraph 0086; 0087; 0088; 0089; 0090
(2017/08/19)
-
- Method for synthesizing N-alkylamide
-
The invention discloses a method for synthesizing N-alkylamide. In a reaction container, adding nitrile, a complex of a transition-metal catalyst gold, a solvent tetrahydrofuran and H2O; reacting a reaction mixture for several hours at the temperature of 130-140 DEG C, cooling the reaction mixture to room temperature, performing vacuum pressure reduction to remove the solvent; adding a compound alcohol, alkali, the complex of a transition-metal catalyst iridium, a solvent toluene, reacting the reaction mixture for several hours at the temperature of 130 DEG C, through column separation, obtaining a target compound. According to the invention, with participation of the transition-metal catalyst, commercial nitrile is hydrolyzed to generate an amide intermediate, and then is subjected to an alkylation reaction with alcohol to obtain N-alkylamide. The reaction has three obvious advantages: 1) the commercial nitrile and alcohol which is almost nontoxic are taken as initial raw materials; 2) only water is generated as a by-product in the reaction, so that the reaction has no harm on environment; and 3) reaction atom economy is high. The reaction accords with green chemistry requirement, and has wide development prospect.
- -
-
-
- Transamidation of carboxamides with amines over nanosized zeolite beta under solvent-free conditions
-
A highly efficient approach to transamidation of carboxamides with amines over nanosized zeolite beta under solvent-free conditions has been successfully demonstrated. Transamidation of a variety of amides with amines produced the respective N-alkyl amides in moderate to excellent yields.
- Durgaiah, Chevella,Naresh, Mameda,Swamy, Peraka,Srujana, Kodumuri,Rammurthy, Banothu,Narender, Nama
-
-
- Tert -Butyl Peroxybenzoate Mediated Selective and Mild N-Benzoylation of Ammonia/Amines under Catalyst- and Solvent-Free Conditions
-
A new protocol for the synthesis of amides from tert-butyl peroxybenzoate (TBPB) and ammonia/amines has been developed under catalyst- and solvent-free conditions. The ammonia, primary and secondary amines reacted smoothly with TBPB to furnish the corresponding primary, secondary, and tertiary amides in excellent yields. TBPB proved to be an efficient and highly chemoselective benzoylating reagent for aliphatic amines in the presence of aromatic amines/hydroxyl groups.
- Yadav, Dilip Kumar T.,Bhanage, Bhalchandra M.
-
supporting information
p. 1862 - 1866
(2015/08/06)
-
- A Heterogeneous Niobium(V) Oxide Catalyst for the Direct Amidation of Esters
-
This study reports the first example of a heterogeneous catalytic system for the direct amidation of various esters with amines. Of 25 types of catalyst, Nb2O5 shows the highest activity in the amidation of methyl benzoate with aniline. Nb2O5 gives high yields in the amidation of various esters and amines under solvent-free conditions, is reusable, and shows higher turnover numbers than previously reported homogeneous catalysts such as La(OTf)3. IR spectroscopic studies of ethyl acetate adsorbed on the catalysts show a strong acid-base interaction between the Nb5+ Lewis acid site and carbonyl oxygen, which can result in high reactivity of the ester with a nucleophile (amine) and, thus, high activity of Nb2O5. Kinetic results show that the activity of Nb2O5 does not markedly decrease with increasing aniline concentration, in contrast to reference catalysts TiO2 and La(OTf)3. The relatively low negative impact of basic molecules on the Lewis acid catalysis of Nb2O5 also enables its high activity.
- Ali, Md. Ayub,Siddiki, S. M. A. Hakim,Kon, Kenichi,Shimizu, Ken-Ichi
-
p. 2705 - 2710
(2015/09/15)
-
- Combination of gold and iridium catalysts for the synthesis of N-alkylated amides from nitriles and alcohols
-
An alternative and efficient approach for the synthesis of N-alkylated amides from nitriles and alcohols was proposed and accomplished. By the combination of [(IPr)Au(NTf2)] (IPr = 1,3-bis(diisopropylphenyl)imidazol-2-ylidene) and [CpIrCl2]2 (Cp = η5-pentamethylcyclopentadienyl), a series of nitriles were first hydrated to give amides, in which the resulting amides were further N-alkylated with a variety of alcohols as alkylating agents to afford N-alkylated amides with good to excellent yields. Compared with previous methods for the synthesis of N-alkylated amides from nitriles and alcohols as starting materials, this protocol could be accomplished with high atom economy under more environmentally benign conditions.
- Li, Feng,Ma, Juan,Lu, Lei,Bao, Xiaofeng,Tang, Wanying
-
p. 1953 - 1960
(2015/04/27)
-
- A flexible approach to Pd-catalyzed carbonylations via aroyl dimethylaminopyridinium salts
-
4-Dimethylaminopyridine (DMAP) is shown to undergo Pd/PtBu3 catalyzed coupling with aryl halides and carbon monoxide to form electrophilic aroyl-DMAP salts. The reaction is easily scalable to prepare multigram quantities with low catalyst loadings, while the precipitation of these salts as they form leads to products with low impurities. These reagents rapidly react with a variety of nucleophiles, including those that contain potentially incompatible functional groups under standard carbonylative conditions.
- Quesnel, Jeffrey S.,Fabrikant, Alexander,Arndtsen, Bruce A.
-
p. 295 - 300
(2015/12/30)
-
- Copper-Catalyzed N-Benzoylation of Amines via Aerobic C-C Bond Cleavage
-
A general copper/air catalytic system for selectively oxidative C-C bond cleavage of 1,2-diarylethan-1-one has been developed, giving aromatic aldehydes and N-benzoylation products of various amines in moderate to excellent yields. This research provides an alternative approach for the N-benzoylation of amine in mild and neutral conditions.
- Fan, Wenyou,Yang, Youqing,Lei, Jianhua,Jiang, Qijian,Zhou, Wang
-
p. 8782 - 8789
(2015/09/15)
-
- A One-Pot, fast, and efficient amidation of carboxylic acids, α-amino acids and sulfonic acids using pph3/n-chlorobenzotriazole system
-
Triphenylphosphine (PPh3)/N-chlorobenzotriazole (NCBT), and amine (primary and secondary aliphatic amines and also substituted anilines) in CH2Cl2 efficiently converted carboxylic acids, α-amino acids, and sulfonic acids to the corresponding amides and sulfonamides at room temperature. Good to excellent yields, inexpensive, and fast reaction conditions are the important features of this procedure.
- Rouhi-Saadabad, Hamed,Akhlaghinia, Batool
-
p. 1703 - 1714
(2015/09/15)
-
- Chloroform as a Carbon Monoxide Precursor: In or Ex Situ Generation of CO for Pd-Catalyzed Aminocarbonylations
-
Conditions for the rapid hydrolysis of chloroform to carbon monoxide (CO) using heterogeneous CsOH·H2O are described. CO and 13CO can be generated cleanly and rapidly under mild conditions and can be captured either in or ex situ in palladium-catalyzed aminocarbonylation reactions. Utilizing only 1-3 equiv of CO allows for the aminocarbonylation of aryl, vinyl, and benzyl halides with a wide variety of primary and secondary amines giving amide products in good to excellent yields. (Chemical Equation Presented).
- Gockel, Samuel N.,Hull, Kami L.
-
supporting information
p. 3236 - 3239
(2015/07/15)
-
- Ce(III) immobilised on aminated epichlorohydrin-activated agarose matrix - "green" and efficient catalyst for transamidation of carboxamides
-
The present study reports the preparation and characterisation of Ce(III) immobilised on an aminated epichlorohydrin-activated agarose matrix (CAEA) as a "green" catalyst. The catalyst was synthesised by the reaction of the epichlorohydrin-activated agarose matrix with ammonia solution, which was then treated with Ce(NO3)3 · 6H2O. The catalyst (CAEA) was characterised by FT-IR, far IR, CHN, XRD, TGA, and ICP techniques. CAEA is shown to be an effective and reusable heterogeneous catalyst for the transamidation of carboxamides with amines under solventfree conditions. The catalyst was successfully applied to the synthesis of a wide range of aromatic and aliphatic amides. High efficiency, mild reaction conditions, easy work-up, simple separation and also reusability are important advantages of this catalyst.
- Zarei, Zeinab,Akhlaghinia, Batool
-
p. 1421 - 1437
(2015/09/15)
-
- The direct synthesis of N-alkylated amides via a tandem hydration/N-alkylation reaction from nitriles, aldoximes and alcohols
-
A novel strategy for the direct synthesis of N-alkylated amides from nitriles, aldoximes and alcohols was proposed and accomplished in the presence of a Cp*Ir complex. This journal is the Partner Organisations 2014.
- Wang, Nana,Zou, Xiaoyuan,Ma, Juan,Li, Feng
-
p. 8303 - 8305
(2014/07/22)
-
- Benzoic acid-catalyzed transamidation reactions of carboxamides, phthalimide, ureas and thioamide with amines
-
An efficient and simple method for the transamidation of carboxamides, phthalimide, ureas and thioamide with amines catalyzed by commercially available benzoic acid under metal-free conditions is described. Furthermore, to the best of our knowledge, this is the first report about the transamidation of an aromatic thioamide with amines.
- Wu, Ji-Wei,Wu, Ya-Dong,Dai, Jian-Jun,Xu, Hua-Jian
-
supporting information
p. 2429 - 2436
(2014/09/30)
-
- Green synthesis of benzamides in solvent- and activation-free conditions
-
Herein, we describe a clean and ecocompatible pathway for both N-benzoylation and N-acetylation of anilines, amines, diamines, and aminoalcohols using three enol esters with good yields. We have improved the use of vinyl benzoate for the direct introduction of a benzamido-moiety under solvent- and activation-free conditions. The recovered amides are easily isolated by crystallization. Copyright
- Alalla, Affef,Merabet-Khelassi, Mounia,Aribi-Zouioueche, Louisa,Riant, Olivier
-
supporting information
p. 2364 - 2376
(2014/07/22)
-
- One-pot stibine modified Co2(CO)8 catalyzed reductive N-alkylation of primary amides with carbonyl compounds
-
A one-pot stibine modified Co2(CO)8 homogeneous catalytic reductive N-alkylation of primary amides using aldehydes/ketones as alkylating agents, is reported. Good to excellent yields of a wide range of secondary amides are obtained (up to 97%) under relative mild conditions.
- Rubio-Pérez, Laura,Sharma, Pankaj,Pérez-Flores, F. Javier,Velasco, Luis,Arias, J. Luis.,Cabrera, Armando
-
experimental part
p. 2342 - 2348
(2012/04/10)
-
- Aqueous-phase deactivation and intramolecular [2 + 2 + 2] cycloaddition of oxanorbornadiene esters
-
Both inter- and intramolecular degradation pathways were identified for the aqueous phase deactivation of oxanorbornadiene (OND) electrophiles, and propargylic OND esters were found to undergo facile intramolecular [2 + 2 + 2] homo-Diels-Alder cycloaddition in polar media.
- Kislukhin, Alexander A.,Higginson, Cody J.,Finn
-
supporting information; experimental part
p. 1832 - 1835
(2011/06/20)
-
- Efficient microwave access to polysubstituted amidines from imidoylbenzotriazoles
-
Microwave reactions of primary and secondary amines with imidoylbenzotriazoles 6a-w gave diversely substituted amidines 7a-Aa in 76-94% yields. Convenient preparations of a variety of amides 5a-Ab (87-96%) and imidoylbenzotriazoles 6a-w (56-95%) have also been developed using microwave irradiation under mild conditions and short reaction times. These results demonstrate further the advantages of microwave synthesis and introduce a new application of imidoylbenzotriazoles in the preparation of polysubstituted amidines.
- Katritzky, Alan R.,Cai, Chunming,Singh, Sandeep K.
-
p. 3375 - 3380
(2007/10/03)
-
- Alkylation of Rink's amide linker on polystyrene resin: A reductive amination approach to modified amine-linkers for the solid phase synthesis of N-substituted amide derivatives
-
Reductive amination of aldehydes and ketones using sodium cyanoborohydride and Rink's 4-(2',4'-dimethoxyphenyl-aminomethyl)-phenoxymethyl-linked polystyrene resin [Rink's amine linker on copoly-(styrene-1%-divinylbenzene)]1 2 affords high yields of linker-bound, N-alkyl amines with excellent chemical selectivity. Subsequent coupling with acid derivatives gave derivatized N-substituted amides in excellent yields after cleavage from the solid-support.
- Brown, Edward G.,Nuss, John M.
-
p. 8457 - 8460
(2007/10/03)
-
- FORMATION AND REACTIVITY OF DILITHIATED N-FURFURYLBENZAMIDES. SYNTHESIS OF α-SUBSTITUTED N-FURFURYLBENZAMIDES
-
Dianion 3 can be efficiently and regioselectively generated from N-furfurylbenzamide with lithium diisopropylamide/tetrahydrofuran/-78 degC and react with various electrophiles to give α-substituted N-furfurylbenzamide derivatives in good yields.
- Ohno, Kosei,Machida, Minoru
-
p. 4487 - 4488
(2007/10/02)
-
