Regioselective synthesis of pentacyclic heterocycles by sequential [3,3] sigmatropic rearrangement of 2-(4′-aryloxybut-2′-ynyl-mercapto)thiochromen-4-ones

被引：25

作者：

Majumdar, KC ^{[1
]}

Bandyopadhyay, A ^{[1
]}

Biswas, A ^{[1
]}

机构：

[1] Univ Kalyani, Dept Chem, Kalyani 741235, W Bengal, India

来源：

TETRAHEDRON | 2003年 / 59卷 / 28期

关键词：

3,3] sigmatropic rearrangement; regioselective synthesis; sequential Claisen rearrangement; phase-transfer catalysis;

D O I：

10.1016/S0040-4020(03)00784-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A number of 4-aryloxymethyl-7-chlorothiopyrano[2,3-b]thiochromen-5(2H)-ones are regioselectively synthesized in 80-85% yield by the Claisen rearrangement of 2-(4'-aryloxybut-2-ynylmercapto)thiochromen-4-ones in refluxing chlorobenzene for 3 h. These products are then subjected to a second Claisen rearrangement in refluxing N,N-diethylaniline for 6 h to give hitherto unreported pentacyclic heterocycles in 50-55% yield. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：5289 / 5293

页数：5

共 19 条

[1]

Dehmlow E. V., 1993, Phase Transfer Catalysis

[2] Asymmetric claisen rearrangement [J].

Ito, H ;

Taguchi, T .

CHEMICAL SOCIETY REVIEWS, 1999, 28 (01) :43-50

[3] Regioselective synthesis of heterocycles by sigmatropic rearrangement:: passage to 3,11a-dimethyl-6a,11a-dihydro-1H,6H-pyrano[3′,4′:5,6]thiopyrano[4,3-b][1]benzofuran-1-one [J].

Majumdar, KC ;

Kundu, UK ;

Ghosh, S .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (19) :2139-2140

[4] Synthesis of bioactive heterocycles:: tandem reaction of 4-N-(4′-aryloxybut-2′-ynyl),N-methylaminocoumarin with 3-chloroperoxybenzoic acid [J].

Majumdar, KC ;

Samanta, SK .

TETRAHEDRON LETTERS, 2002, 43 (11) :2119-2121

[5] Studies in sigmatropic rearrangement: Synthesis of a [6,6]pyranothiopyran ring system by sequential Claisen rearrangement and pyridine hydrotribromide mediated regioselective "6-endo" cyclization [J].

Majumdar, KC ;

Kundu, UK ;

Ghosh, SK .

ORGANIC LETTERS, 2002, 4 (16) :2629-2631

[6] Studies on sulfoxide rearrangements:: regioselective synthesis of 3-(aryloxyacetyl)-2,3-dihydrothieno[3,2-c][1]benzopyran-4-ones [J].

Majumdar, KC ;

Ghosh, SK .

TETRAHEDRON LETTERS, 2002, 43 (11) :2123-2125

[7] Studies in pyrimidine-annelated heterocycles by tandem cyclization: Regioselective synthesis of [6,6]pyranopyran by intramolecular [1,6] Michael addition [J].

Majumdar, KC ;

Das, U .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (26) :9997-10000

[8]

MAJUMDAR KC, 1991, SYNLETT, P595

[9] REGIOSELECTIVE SYNTHESIS OF 4-(ARYLOXYMETHYL)THIOPYRANO [2,3-B][1]BENZOTHIOPYRAN-5(2H)-ONES [J].

MAJUMDAR, KC ;

KHAN, AT ;

SAHA, S .

SYNTHETIC COMMUNICATIONS, 1992, 22 (06) :901-912

[10] Studies of bioactive heterocycles:: amino Claisen rearrangement of 4-N-(4-aryloxybut-2-ynyl),N-methylaminocoumarins [J].

Majumdar, KC ;

Bhattacharyya, T .

TETRAHEDRON LETTERS, 2001, 42 (25) :4231-4233

← 1 2 →