Synthesis and reactivity of hexahydropyrroloquinolines

被引：69

作者：

Hadden, M ^{[1
]}

Nieuwenhuyzen, M ^{[1
]}

Potts, D ^{[1
]}

Stevenson, PJ ^{[1
]}

Thompson, N ^{[1
]}

机构：

[1] Queens Univ Belfast, Sch Chem, Belfast BT9 5AG, Antrim, North Ireland

来源：

TETRAHEDRON | 2001年 / 57卷 / 26期

关键词：

martinellic acid; martinelline; imino Diels-Alder reaction; cyclic enamide; indium trichloride;

D O I：

10.1016/S0040-4020(01)00466-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Formal [4+2] cycloaddition of cyclic enamides with imines derived from aromatic amines gave the 4-arylhexahydropyrroloquinoline skeleton in one step as mixtures of diastereoisomers. Aromatic imines derived from formaldehyde and methylglyoxalate also participated in this chemistry, with the latter favouring formation of the endo-cycloadduct. The cycloadducts derived from methylglyoxalate were unstable and fragmented to give highly substituted quinolines under both neutral and basic conditions. Imines derived from 3-cyanoacrolein also underwent cycloaddition and gave an advanced potential precursor to martinellic acid, albeit with poor diastereoselectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：5615 / 5624

页数：10

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