USE OF FUNCTIONALIZED YNAMINES IN A HETERO-DIELS-ALDER APPROACH TO DIHYDRONAPHTHO[1,2-B]PYRANS AND INDENO[1,2-B]PYRANS

被引：14

作者：

BLOXHAM, J ^{[1
]}

DELL, CP ^{[1
]}

机构：

[1] ELI LILLY & CO,LILLY RES CTR,ERL WOOD MANOR,WINDLESHAM GU20 6PH,SURREY,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1993年 / 24期

关键词：

D O I：

10.1039/p19930003055

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of the ynamine ester methyl 3-(pyrrolidin-1-yl)prop-2-ynoate 5 with 2-(4-nitrobenzylidene)-1-tetralone 1 results in a very poor yield of the chromatographically labile 4-aryl-5,6-dihydro-4H-naphtho[1,2-b]pyran 8 along with the alpha-pyrone 10. Increasing the reactivity of the 4pi component by using the 2-arylidene indan-1,3-diones 11-13 results in moderate to good yields of the 4-aryl-5-oxo-4H-indeno[1,2-b]pyran-3-carboxylates 14-19. An ynamine nitrile 24, generated in situ, also reacts with 12 and 13, furnishing rather lower yields of the adducts 20 and 21.

引用

页码：3055 / 3059

页数：5

共 39 条

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