REACTIONS OF URACILS .21. ZWITTERIONIC HETEROPOLYCYCLIC URACILS BY A NOVEL 3-COMPONENT REACTION - IMINOPHOSPHORANE, ISOCYANATE, HETEROARENE

被引：49

作者：

WAMHOFF, H

SCHMIDT, A

机构：

[1] Institut für Organische Chemie und Biochemie, Universität Bonn, D-53121 Bonn

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 25期

关键词：

D O I：

10.1021/jo00077a013

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The novel three-component reaction of (uracil-6-ylimino)phosphorane 1, isocyanate 2, and (substituted) pyridines gives, in a one-pot procedure, a variety of new pyrido[ 1',2':3,41 pyrimido[4,5-d]pyrimidines 3-11. The zwitterionic ground state of these new ring systems is i.a. established by means of solvatochromism, Hammett correlations, NMR, and X-ray analysis. Replacement of the pyridine by isoquinoline and phthalazine gives access to the novel ring systems pyrimido[4',5':4,5]pyrimido-[6,1-a]isoquinoline and -phthalazine, which are formed as dihydro derivatives (14, 15) or as zwitterions (13,17), depending on there action conditions. Oxidative cleavage of the phthalazine 15 in nitrobenzene affords the pyrimido[4,5-d]pyrimidines 16.

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页码：6976 / 6984

页数：9

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