CAN-promoted, diastereoselective synthesis of fused 2,3-dihydrofurans and their transformation into tetrahydroindoles

被引：32

作者：

Maiti, Swarupananda ^{[1
]}

Perumal, Paramasivan T. ^{[1
,2
]}

Carlos Menendez, J. ^{[1
]}

机构：

[1] Univ Complutense, Fac Farm, Dept Quim Organ & Farmaceut, E-28040 Madrid, Spain

[2] Cent Leather Res Inst, Div Organ Chem, Madras 600020, Tamil Nadu, India

来源：

TETRAHEDRON | 2010年 / 66卷 / 49期

关键词：

D O I：

10.1016/j.tet.2010.10.017

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction between 1 3-cyclohexanediones and chalcones (or their vinilogs) in the presence of 2 5 equiv of cerium(IV) ammonium nitrate afforded trans-2-arylcarbonyl-3-aryl (or styryl)-2 3 6 7-tetrahydrobenzofuran-4(5H)-ones in good to excellent yields and in high diastereoselectivities The method was also extended to the preparation of derivatives of the 5 6-dihydro-2H-cyclopenta[b]furan-4(3H)-one system The fused 2 3-dihydrofuran derivatives were transformed into 1-alkyl-2-acyl-3-aryl-6 7-dihydroindole-4(5H)-ones by 2 3-dehydrogenation followed by reaction with primary amines The direct reaction of the tetrahydrobenzofuran-4(5H)-one compounds derived from dimedone with amines gave 1-alkyl-2-alkylimino-3-aryl-6 7-dihydroindole-4(5H)-ones while starting materials derived from 1 3-cyclohexanedione underwent an unprecedented 2-deacylation reaction and gave 1-alkyl-3-aryl-6 7-dihydroindole-4(5H)-ones (C) 2010 Elsevier Ltd All rights reserved

引用

页码：9512 / 9518

页数：7

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