CHEMISTRY OF DIAMINOMALEONITRILE .5. DIHYDROPYRAZINE SYNTHESIS

被引：15

作者：

OHTSUKA, Y ^{[1
]}

TOHMA, E ^{[1
]}

KOJIMA, S ^{[1
]}

TOMITA, N ^{[1
]}

机构：

[1] NIPPON SODA CO LTD,CHIYODA KU,TOKYO 100,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1979年 / 44卷 / 26期

关键词：

D O I：

10.1021/jo00394a027

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Condensation of aldehydes with diaminomaleonitrile (DAMN) Schiff bases in the presence of triethylamine at temperatures below 20°C is accompanied by regiospecific hydration of the nitrile groups to give 3-cyanoacrylamide derivatives, which cyclize readily into 1, 2-dihydropyrazines (6 and/or 7). The substituent effect on the product ratio (6/7) is examined, and the reaction mechanism is discussed in terms of a new general reaction pattern of DAMN derivatives. Reactions of 6 and 7 by oxidation, reduction, hydantoin formation with isocyanates, and cyanoethylation are also investigated. © 1979, American Chemical Society. All rights reserved.

引用

页码：4871 / 4876

页数：6

共 21 条

[1] HYDROGEN-CYANIDE CHEMISTRY .8. NEW CHEMISTRY OF DIAMINOMALEONITRILE - HETEROCYCLIC SYNTHESIS [J].