One-carbon homologation of aldehydes to N-(α-haloacyl)benzotriazoles

被引：11

作者：

Katritzky, Alan R. ^{[1
]}

Tala, Srinivasa R. ^{[1
]}

Singh, Sandeep K. ^{[1
]}

机构：

[1] Univ Florida, Dept Chem, Ctr Heterocycl Cpds, Gainesville, FL 32611 USA

来源：

SYNTHESIS-STUTTGART | 2006年 / 19期

关键词：

N-acylbenzotriazole; homologation; aldehyde; acylation; N-halosuccinimide;

D O I：

10.1055/s-2006-950183

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

One-carbon homologated N-(alpha-haloacyl)benzotriazoles have been synthesized from the corresponding aromatic and aliphatic aldehydes. Vinylbenzotriazoles, prepared by the reaction of aldehydes with the one-carbon synthon BtCH(2)P(+)Ph(3)Cl(-), were subsequently treated with Br-2/Et3N to give 1-bromovinylbenzotriazoles. These were then treated with NBS/NIS in CH3CN-H2O to furnish one-carbon homologated N-(alpha-haloacyl)benzotriazoles in 53-77% yields. We have also demonstrated the utility of these new reagents in organic synthesis.

引用

页码：3231 / 3237

页数：7

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