An efficient reduction of N-substituted carbonylimidazolides into formamides by NaBH4

被引:6
作者
Chen, Zhiyong [1 ]
Cao, Yiming [1 ]
Tian, Zeyu [1 ]
Zhou, Xuan [1 ]
Xu, Wenjin [1 ]
Yang, Jia [1 ]
Teng, Hanbing [1 ]
机构
[1] Wuhan Univ Technol, Sch Chem Chem Engn & Life Sci, 122 Luoshi Rd, Wuhan 430070, Peoples R China
关键词
N-Substituted carbonylimidazolide; Formamide; Reduction; Sodium borohydride; AMINO-ACIDS/PEPTIDE-ACIDS; RETRO-INVERSO PEPTIDES; ASYMMETRIC ALLYLATION; EMPLOYING ISOCYANATES; ONE-POT; CARBAMOYLIMIDAZOLE; ORGANOCATALYSIS; ISOCYANIDES; DERIVATIVES; SULFIDE;
D O I
10.1016/j.tetlet.2017.04.072
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel, simple and versatile protocol was investigated for highly efficient synthesis of formamides through reducing N-substituted carbonylimidazolides by NaBH4 under mild reaction conditions. By this method, not only carboxylic acids or isocyanates, but also amines can readily access formamides with high yields. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2166 / 2170
页数:5
相关论文
共 52 条
[1]   Organocatalysis with chiral formamides: Asymmetric allylation and reduction of imines [J].
Baudequin, Christine ;
Chaturvedi, Devdutt ;
Tsogoeva, Svetlana B. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (16) :2623-2629
[2]   Synthesis of (R)-, (S)-, and (RS)-hydroxymethylmexiletine, one of the major metabolites of mexiletine [J].
Cavalluzzi, Maria Maddalena ;
Catalano, Alessia ;
Bruno, Claudio ;
Lovece, Angelo ;
Carocci, Alessia ;
Corbo, Filomena ;
Franchini, Carlo ;
Lentini, Giovanni ;
Tortorella, Vincenzo .
TETRAHEDRON-ASYMMETRY, 2007, 18 (20) :2409-2417
[3]   Total synthesis of sequential retro-peptide oligomers [J].
Ceretti, S ;
Luppi, G ;
De Pol, S ;
Formaggio, F ;
Crisma, M ;
Toniolo, C ;
Tomasini, C .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (20) :4188-4196
[4]   A new facile method for the synthesis of 1-arylimidazole-5-carboxylates [J].
Chen, BC ;
Bednarz, MS ;
Zhao, RL ;
Sundeen, JE ;
Chen, P ;
Shen, ZQ ;
Skoumbourdis, AP ;
Barrish, JC .
TETRAHEDRON LETTERS, 2000, 41 (29) :5453-5456
[5]   PARTIALLY MODIFIED RETRO-INVERSO PEPTIDES - COMPARATIVE CURTIUS REARRANGEMENTS TO PREPARE 1,1-DIAMINOALKANE DERIVATIVES [J].
CHOREV, M ;
GOODMAN, M .
INTERNATIONAL JOURNAL OF PEPTIDE AND PROTEIN RESEARCH, 1983, 21 (03) :258-268
[6]  
Christian J, 2014, J MED CHEM, V57, P7590
[7]   Nano rod-shaped and reusable basic Al2O3 catalyst for N-formylation of amines under solvent-free conditions: A novel, practical and convenient 'NOSE' approach [J].
Das, Vijay Kumar ;
Devi, Rashmi Rekha ;
Raul, Prasanta Kumar ;
Thakur, Ashim Jyoti .
GREEN CHEMISTRY, 2012, 14 (03) :847-854
[8]   Competitive Intramolecular Hydrogen Bonding in Oligo(ethylene oxide) Substituted Quadruple Hydrogen Bonded Systems [J].
de Greef, Tom F. A. ;
Nieuwenhuizen, Marko M. L. ;
Sijbesma, Rint P. ;
Meijer, E. W. .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (03) :598-610
[9]   Total Synthesis of an Oxepine Natural Product, (±)-Janoxepin [J].
Doveston, Richard G. ;
Steendam, Rene ;
Jones, Stuart ;
Taylor, Richard J. K. .
ORGANIC LETTERS, 2012, 14 (04) :1122-1125
[10]   Synthesis and Reactivity of N-Alkyl Carbamoylimidazoles: Development of N-Methyl Carbamoylimidazole as a Methyl Isocyanate Equivalent [J].
Duspara, Petar A. ;
Islam, Md. Sadequl ;
Lough, Alan J. ;
Batey, Robert A. .
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (22) :10362-10368