On the Chemistry of Cinnoline I. Synthesis and Reactions of (4-Amino-cinnolin-3-yl)-p-tolyl-methanonesZur Chemie der Cinnoline, 1. Mitt. Synthese und Reaktionen von(4-Amino-cinnolin-3-yl)-p-tolyl-methanonen

被引：4

作者：

Atef M. Amer

Mohamed A. El-Bermaui

Ahmed F. S. Ahmed

Somya M. Soliman

机构：

[1] Chemistry Department,

[2] Faculty of Science,undefined

[3] Zagazig University,undefined

[4] Zagazig,undefined

[5] Egypt,undefined

[6] Organic Chemistry Department,undefined

[7] Faculty of Pharmacy,undefined

[8] Zagazig University,undefined

[9] Zagazig,undefined

[10] Egypt,undefined

来源：

Monatshefte für Chemie / Chemical Monthly | 1999年 / 130卷 / 11期

关键词：

Keywords. Cycloadditions; Hydrazones; Cinnolines; Pyridines; Pyrimidines.;

D O I：

10.1007/PL00010201

中图分类号：

学科分类号：

摘要：

The synthesis of a series of (4-Amino-cinnolin-3-yl)-p-tolyl-methanones from aryl-hydrazonomalononitrile in a one step procedure is reported. The (4-amino-cinnolin-3-yl)-p-tolyl-methanones could be annelated to the corresponding 1,2-dihydro-4-(p-tolyl)-2-oxopyrido[3,2-c]cinnoline derivatives via (4-acetamido-cinnolin-3-yl)-p-tolyl-methanones. Treatment of 1,2-dihydro-9-methyl-4-(p-tolyl)-pyrido[3,2-c]cinnoline-2-one with POCl3 and P2S5 gave 2-chloro-9-methyl-4-(p-tolyl)-pyrido[3,2-c]cinnoline and 1,2-dihydro-9-methyl-4-(p-tolyl)-pyrido[3,2-c]cinnoline-2-thione. Treatment of the ketone with malononitrile afforded 2-amino-3-cyano-9-methyl-4-(p-tolyl)-pyrido[3,2-c]cinnoline. Using these ketones, a facile and convenient route towards substituted pyrimidino[5,4-c]-cinnolines was developed. Chemical and spectroscopic evidences for the structures of the new compounds are presented.

引用

页码：1409 / 1418

页数：9