[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

[41] SYNTHESIS OF (+)-HINOKIOL, (+)-HINOKIONE, (+)-SALVIOL, AND (+)-2-OXOFERRUGINOL
MATSUMOTO, T
USUI, S
KAWASHIMA, H
MITSUKI, M
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1981, 54 (02) : 581 - 584
[42] MCDONALD E, 1978, TETRAHEDRON LETT, P4723
[43] Highly regioselective 1,2-addition of alkoxybenzyl Grignard reagents to α-oxoketene dithioacetals:: A facile regiocontrolled synthesis of alkoxynaphthalenes and their condensed analogs via aromatic annelation
Mehta, BK
Nandi, S
Ila, H
Junjappa, H
[J]. TETRAHEDRON, 1999, 55 (44) : 12843 - 12852
[44] NEW SYNTHESIS OF SUBSTITUTED BIPHENYLS, BIARYLS, AND TERPHENYLS FROM ARYLIDENEMALONODINITRILES, ETHYL PYRUVATE, AND MALONODINITRILE
MILART, P
SEPIOL, J
[J]. TETRAHEDRON LETTERS, 1990, 31 (19) : 2735 - 2738
[45] STRUCTURE OF JUNCUSOL - NOVEL CYTOTOXIC DIHYDROPHENANTHRENE FROM ESTUARINE MARSH PLANT JUNCUS-ROEMERIANUS
MILES, DH
BHATTACHARYYA, J
MODY, NV
ATWOOD, JL
BLACK, S
HEDIN, PA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (02) : 618 - 620
[46] Domino carbocationic rearrangement of α-[bis(methylthio)methylene]alkyl-2-arylcyclopropyl carbinols:: Facile access to 1-arylindanes
Mohanta, PK
Peruncheralathan, S
Ila, H
Junjappa, H
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (04) : 1503 - 1508
[47] CONJUGATED KETENES - NEW ASPECTS OF THEIR SYNTHESIS AND SELECTED UTILITY FOR THE SYNTHESIS OF PHENOLS, HYDROQUINONES, AND QUINONES
MOORE, HW
DECKER, OHW
[J]. CHEMICAL REVIEWS, 1986, 86 (05) : 821 - 830
[48] MYRBOH B, 1982, SYNTHESIS-STUTTGART, P307
[49] OHASHI M, 1968, TETRAHEDRON LETT, P719
[50] AROMATIC SUBSTITUTION .28. MECHANISM OF ELECTROPHILIC AROMATIC SUBSTITUTIONS
OLAH, GA
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1971, 4 (07) : 240 - &

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