Highly Diastereoselective NHC-Catalyzed [4+3] Annulation of Enals, Aldehydes and N-Phenyl Urea/Thiourea for the Synthesis of Monocyclic trans-1,3-Diazepanes

被引：18

作者：

Siddiqui, Ibadur R. ^{[1
]}

Srivastava, Anjali ^{[1
]}

Shamim, Shayna ^{[1
]}

Srivastava, Arjita ^{[1
]}

Waseem, Malik A. ^{[1
]}

Singh, Rana K. P. ^{[2
]}

机构：

[1] Univ Allahabad, Dept Chem, Lab Green Synth, Allahabad 211002, Uttar Pradesh, India

[2] Univ Allahabad, Dept Chem, Elect Organ & Green Synth Lab, Allahabad 211002, Uttar Pradesh, India

来源：

SYNLETT | 2013年 / 24卷 / 19期

关键词：

N-heterocyclic carbene; diastereoselective; 1,3-diazepane; multicomponent; one-pot reaction; HETEROCYCLIC CARBENES; ALPHA; BETA-UNSATURATED ALDEHYDES; CONJUGATE UMPOLUNG; CONVERSION;

D O I：

10.1055/s-0033-1339894

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Heterocyclic carbene catalyzed synthesis of 1,3-diazepanes from ,-unsaturated aldehydes, N-phenyl urea/thiourea and aromatic aldehydes has been developed. The reactive Breslow intermediate, formed by reaction of the enal with the NHC, attacks as a d(3) nucleophile at the 1-arylidene-3-arylurea derivative, which is produced by simple reaction of N-phenyl urea/thiourea with an aromatic aldehyde. The resulting intermediate, on subsequent heterocyclization, forms the product with high yield. The reaction proceeded smoothly with high atom economy, producing a new C-C and a new C-N bond in a one-pot operation.

引用

页码：2586 / 2590

页数：5

共 34 条

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