6-chloro-spirocyclohexenindol-2-ones: an unusual ring transformation to ethyl 2-(cyclohexa-1,4-dienyl)phenylcarbamates.

被引：12

作者：

Beccalli, EM ^{[1
]}

Clerici, F ^{[1
]}

Gelmi, ML ^{[1
]}

机构：

[1] Univ Milan, Fac Farm, Ist Chim Organ, I-20133 Milan, Italy

来源：

TETRAHEDRON | 1999年 / 55卷 / 28期

关键词：

Diels-Alder; chloromethylen-2-indolone; (cyclohexadienyl)phenylcarbamates; 2-aminobiphenyl; phenanthridone;

D O I：

10.1016/S0040-4020(99)00475-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Diels-Alder cycloaddition reaction of 3-chloromethylen-2-indolones 1 with a series of dienes 2 was studied in order to synthesize spirocyclohexenindolones 3 and 4. The reaction proceeded with good diastereoselectivity and regioselectivity. Chloro spirocyclohexenindolones 3 and 4 were transformed into 2-aminobiphenyl derivatives 5 by reacting with sodium ethoxide. Starting from the indolone 1c and 2,3-dimethylbutadiene the spiro compounds 3f and 4e were obtained. On treatment with sodium ethoxide, 3f was transformed into the phenanthridone derivatives 7 and 8. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

引用

页码：8579 / 8586

页数：8

共 11 条

[1] AVENOZA A, 1995, SYNTHESIS-STUTTGART, P671
[2] SYNTHESIS OF 3-ACYL-3-ALKYLOXINDOLES
FLANN, CJ
OVERMAN, LE
SARKAR, AK
[J]. TETRAHEDRON LETTERS, 1991, 32 (48) : 6993 - 6996
[3] REGIOSPECIFIC FORMATION OF 1,3-DIENES BY THE PALLADIUM CATALYZED INTRA-MOLECULAR AND INTER-MOLECULAR COUPLING OF VINYL HALIDES
GRIGG, R
STEVENSON, P
WORAKUN, T
[J]. TETRAHEDRON, 1988, 44 (07) : 2049 - 2054
[4] JOSHI KC, 1985, HETEROCYCLES, V23, P957
[5] IMINE-BRIDGED PLANAR POLY(P-PHENYLENE) DERIVATIVES FOR MAXIMIZATION OF EXTENDED PI-CONJUGATION - THE COMMON INTERMEDIATE APPROACH
LAMBA, JJS
TOUR, JM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (26) : 11723 - 11736
[6] ON THE STRUCTURE OF THE DIELS-ALDER ADDUCTS OBTAINED FROM (E)-3-METHOXYCARBONYLMETHYLENE-2-OXOINDOLINE WITH UNSYMMETRICAL BUTADIENE DERIVATIVES
OKADA, K
KONDO, M
TANINO, H
KAKOI, H
INOUE, S
[J]. HETEROCYCLES, 1992, 34 (03) : 589 - 597
[7] DIELS-ALDER REACTION OF 3-METHOXYCARBONYLMETHYLENE-2-OXOINDOLINE DERIVATIVES WITH UNSYMMETRICAL BUTADIENES
OKADA, K
SAKUMA, H
KONDO, M
INOUE, S
[J]. CHEMISTRY LETTERS, 1979, (03) : 213 - 216
[8] THE DIELS-ALDER REACTION OF ISOPRENE WITH 2-OXOINDOLIN-3-YLIDENE DERIVATIVES
RICHARDS, CG
THURSTON, DE
[J]. TETRAHEDRON, 1983, 39 (10) : 1817 - 1821
[9] RICHARDS CG, 1968, TETRAHEDRON LETT, P4391
[10] SIVASUBRAMANIAN S, 1981, INDIAN J CHEM B, V20, P552

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