Preparation of α-(2,2-diphenylhydrazino)lactones and related compounds by radical cyclization:: Use of glyoxylic acid hydrazone derivatives

被引：20

作者：

Clive, DLJ ^{[1
]}

Zhang, JH ^{[1
]}

Subedi, R ^{[1
]}

Bouétard, V ^{[1
]}

Hiebert, S ^{[1
]}

Ewanuk, R ^{[1
]}

机构：

[1] Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 04期

关键词：

D O I：

10.1021/jo0013655

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Glyoxylic acid diphenylhydrazone (2a) and the corresponding O-benzyloxime (2b) are easily esterified in high yield by beta -bromo alcohols. The resulting esters undergo radical cyclization to alpha-(2,2-diphenylhydrazino)- or alpha-[(phenylmethoxy)amino]lactones on treatment with tributyltin hydride. Esters for radical cyclization were also made using a beta-(phenylseleno) alcohol and an enol ether. Several derivatives of glyoxylic acid were evaluated, but none was as effective as 2a or 2b. The imine 28 was prepared by an indirect route; it undergoes radical cyclization with displacement of the nitrogen substituent (28 --> 30) so that an alpha -amino lactone can be generated by acid hydrolysis of the cyclization product.

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页码：1233 / 1241

页数：9

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