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
收藏
页码：366 / 369
页数：4
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