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
收藏
页码：769 / 775
页数：7
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