NOVEL REDOX CYCLIZATION PRODUCTS DERIVED FROM 2-ACYLPYRROLES AND TRANS-3-BROMO-3,4-DIHYDRO-4-HYDROXY-2,2-DIMETHYL-2H-CHROMENE-6-CARBONITRILE

被引：2

作者：

BUCKLE, DR ^{[1
]}

CONNOR, SC ^{[1
]}

EGGLESTON, DS ^{[1
]}

FALLER, A ^{[1
]}

PINTO, IL ^{[1
]}

READSHAW, SA ^{[1
]}

SMITH, DG ^{[1
]}

机构：

[1] SMITHKLINE BEECHAM PHARMACEUT,DEPT PHYS & STRUCT CHEM,KING OF PRUSSIA,PA 19406

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1992年 / 07期

关键词：

D O I：

10.1039/p19920000769

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of 2-(trifluoroacetyl)pyrrole with trans-3-bromo-3,4-dihydro-4-hydroxy-2,2-dimethyl-2H-chromene-6-carbonitrile under basic conditions has been shown to afford high yields of (4R*,5aS*,11bS*)-5a-hydroxy-6,6-dimethyl-4-trifluoromethyl-5a,11b-dihydro-4H,6H-pyrrolo[1',2':4,5]-oxazino[2,3-c]chromene-10-carbonitrile rather than the anticipated amino alcohol. The unequivocal structural assignment of this unusual tetracyclic product by spectroscopic and X-ray crystallographic techniques is described and possible mechanistic explanations for its formation are discussed. Analogous reactions of pyrroles substituted in the 2-position by formyl, acetyl and benzoyl moieties have been shown to behave in an essentially similar manner, suggesting that the reaction is general for 2-acylpyrroles.

引用

页码：769 / 775

页数：7

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