21719-91-5Relevant academic research and scientific papers
Combination of air/moisture/ambient temperature compatible organolithium chemistry with sustainable solvents: Selective and efficient synthesis of guanidines and amidines
Anti?olo, Antonio,Carrillo-Hermosilla, Fernando,Elorriaga, David,García-álvarez, Joaquín,Parra-Cadenas, Blanca
supporting information, p. 800 - 812 (2022/02/02)
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
An eco-friendly approach for the synthesis of 1,2,5-trisubstituted and 4-amino-1,2,5-tetrasubstituted imidazoles via a multi-component condensation
Mehrabi, Hossein,Alizadeh-Bami, Farzaneh,Meydani, Azam,Besharat, Soheila
, p. 86 - 95 (2021/04/02)
The synthesis of 1,2,5-trisubstituted and 4-amino-1,2,5-tetrasubstituted imidazoles was demonstrated via a two-step cyclo-condensation reaction of aryl amines, carbonitriles, and ethyl bromopyruvate or aryl amines and arylglyoxals in ethanol heated under
Transition-Metal-Free Synthesis of 1,2-diphenyl-1H-benzo[d] Imidazole Derivatives from N-phenylbenzimidamides and Cyclohexanones
Lu, Guoqiang,Luo, Nan,Hu, Fangpeng,Ban, Zihui,Zhan, Zhenzhen,Huang, Guo-Sheng
supporting information, p. 487 - 492 (2019/12/12)
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.).
Base-Mediated Amination of Alcohols Using Amidines
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)
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.
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
Alizadeh-Bami, Farzaneh,Hajipour, Mina,Mehrabi, Hossein,Rezazadeh-Jabalbarezi, Fatemeh
, (2020/07/16)
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
Transition-metal-free three-component reaction: Additive controlled synthesis of sulfonylated imidazoles
Liu, Wei,Zhang, Yu,He, Jiaming,Yu, Yue,Yuan, Jiajun,Ye, Xiaoyi,Zhang, Ziwu,Xue, Liang,Cao, Hua
, p. 11348 - 11358 (2019/09/09)
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
Copper-Catalyzed Intramolecular C-H Amination: A New Entry to Substituted Xanthine Derivatives
Shimizu, Maki,Hayama, Noboru,Kimachi, Tetsutaro,Inamoto, Kiyofumi
, p. 4183 - 4190 (2017/09/12)
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..
Synthesis of 2-arylquinazolin-4(3H)-ones by N-aryl benzamidines with aromatic carbonates
Aikawa, Shunichi,Sekiguchi, Chiharu,Yamazaki, Yuko,Hattori, Mika,Isaka, Tatsuya,Yoshida, Yasuhiko,Ihara, Shogo
, p. 343 - 348 (2014/04/17)
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
Copper-catalyzed three-component synthesis of 3-Aminopyrazoles and 4-iminopyrimidines via β-alkynyl-N-sulfonyl ketenimine intermediates
Xing, Yanpeng,Cheng, Binyu,Wang, Jing,Lu, Ping,Wang, Yanguang
supporting information, p. 4814 - 4817 (2015/04/27)
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.
Synthesis of benzimidazoles by PIDA-promoted direct C(sp2)-H imidation of N-arylamidines
Huang, Jinbo,He, Yimiao,Wang, Yong,Zhu, Qiang
supporting information, p. 13964 - 13967 (2013/01/15)
A metal-free synthesis of diversified benzimidazoles from N-arylamidines through a phenyliodine(III) diacetate (PIDA) promoted intramolecular direct C(sp2)-H imidation has been developed. The reaction proceeds smoothly at 0 °C or ambient temperature to provide the desired products in good to excellent yields. The synthesis of 2-alkyl- or 2-alkyl-fused benzimidazoles, which are generally inaccessible by similar Pd- or Cu-catalyzed approaches, can also be achieved. Copyright
