[4 + 2] cycloaromatization of 4-bis(methylthio)-3-buten-2-one with active methylene ketones: A simple and facile phenol annulation

被引：38

作者：

Barun, O ^{[1
]}

Nandi, S ^{[1
]}

Panda, K ^{[1
]}

Ila, H ^{[1
]}

Junjappa, H ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 15期

关键词：

D O I：

10.1021/jo020219r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new method for beta-phenol annulation involving base-induced [4C + 2C] cycloaromatization of readily available 4-bis(methylthio)-3-buten-2-one with a variety of cyclic and acyclic active methylene ketones has been reported. Appropriate choice of ketones allows synthesis of diverse frameworks such as dihydroindan, tetrahydronaphthalenes, their higher homologues, dihydro/octahydrophenanthrenes, anthracene, and heteroannulated analogue in high yields with regiocontrol of phenolic functionality.

引用

页码：5398 / 5401

页数：4

共 70 条

[1] Enantioselective synthesis of cuparane sesquiterpenes. Synthesis of (-)-cuparene and (-)-delta-cuparenol
Abad, A
Agullo, C
Arno, M
Cunat, AC
Garcia, MT
Zaragoza, RJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (17) : 5916 - 5919
[2] STUDIES IN TERPENOIDS .17. SYNTHESIS OF 7-HYDROXYCADALENAL AND SOME RELATED NATURALLY OCCURRING SESQUITERPENOIDS
ALEXANDER, J
KRISHNAR.GS
[J]. TETRAHEDRON, 1971, 27 (03) : 645 - +
[3] Synthesis of functionalized naphthalenes from substituted 1-methoxybenzocyclobutenes
Andersen, NG
Maddaford, SP
Keay, BA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (08) : 2885 - 2887
[4] [Anonymous], 1991, Comprehensive Organic Synthesis
[5] AROMATIC BENZENE COMPOUNDS FROM ACYCLIC PRECURSORS
BAMFIELD, P
GORDON, PF
[J]. CHEMICAL SOCIETY REVIEWS, 1984, 13 (04) : 441 - 488
[6] FULLY REGIOCONTROLLED SYNTHESIS OF DEACETAMIDOISOCOLCHICINE - FORMAL TOTAL SYNTHESIS OF COLCHICINE
BANWELL, MG
LAMBERT, JN
CORBETT, M
GREENWOOD, RJ
GULBIS, JM
MACKAY, MF
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (11): : 1415 - 1426
[7] CONVENIENT SYNTHESES OF 5-SUBSTITUTED 2-HYDROXYBENZOATES AND RELATED REACTIONS
BARTON, DHR
DRESSAIRE, G
WILLIS, BJ
BARRETT, AGM
PFEFFER, M
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (03): : 665 - 669
[8] DIRECTED LITHIATION OF AROMATIC TERTIARY AMIDES - AN EVOLVING SYNTHETIC METHODOLOGY FOR POLYSUBSTITUTED AROMATICS
BEAK, P
SNIECKUS, V
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1982, 15 (10) : 306 - 312
[9] CYCLOBUTANONES AND CYCLOBUTENONES IN NATURE AND IN SYNTHESIS
BELLUS, D
ERNST, B
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (06): : 797 - 827
[10] INVERSE ELECTRON DEMAND DIELS-ALDER REACTION OF 3-CARBOMETHOXY-2-PYRONES WITH 1,1-DIMETHOXYETHYLENE - A SIMPLE AND MILD METHOD OF ARYL ANNULATION
BOGER, DL
MULLICAN, MD
[J]. TETRAHEDRON LETTERS, 1982, 23 (44) : 4551 - 4554

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