DIOXOPYRROLINES .45. [2+2] PHOTOCYCLOADDITION OF 4-ETHOXYCARBONYL-5-ARYL-1H-PYRROLE-2,3-DIONE TO CYCLOPENTENE DERIVATIVES - FORMATION OF DIHYDROPYRIDONES

被引：9

作者：

SANO, T ^{[1
]}

HORIGUCHI, Y ^{[1
]}

IMAFUKU, K ^{[1
]}

TSUDA, Y ^{[1
]}

机构：

[1] KANAZAWA UNIV, FAC PHARMACEUT SCI, KANAZAWA, ISHIKAWA 920, JAPAN

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 1990年 / 38卷 / 02期

关键词：

cyclobutane; cyclopentadiene; cyclopentene; dihydropyridone; dioxopyrroline; donor-acceptor interaction; hydroindole; indene; photocycloaddition; stereoselection rule;

D O I：

10.1248/cpb.38.366

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Photocycloaddition reactions of 4-ethoxycarbonyl-5-aryl-l//-pyrrole-2,3-dione (1) with cyclopentadiene, indene, and cyclopentene gave the dihydropyridones 8, 11, and 12 as major products, respectively. Formation of them can be rationalized by assuming the formation of a 2s + 2a adduct predicted by the stereoselection rule and subsequent skeletal rearrangement. The stereochemical results seem to support the hypothesis that the donor-acceptor interaction as theoretically deduced by Epiotis plays an important role in determining the stereochemical pathway of photo-cycloaddition. © 1990, The Pharmaceutical Society of Japan. All rights reserved.

引用

页码：366 / 369

页数：4

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