Solid-state regioselective cyclization initiated by the electrophilic attack on the double bond by N-bromosuccinimide on montmorillonite K-10 clay support under microwave irradiation

被引：4

作者：

Majumdar, K. C. ^{[1
]}

Rahaman, H. ^{[1
]}

Roy, B. ^{[1
]}

机构：

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

来源：

SYNTHETIC COMMUNICATIONS | 2007年 / 37卷 / 7-9期

关键词：

6-endo cyclization; 4-hydroxy coumarin; 4-hydroxy pyrone; microwave irradiation; N-bromosuccinimide; solid-state reaction;

D O I：

10.1080/00397910701228992

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

3-AllyI-4-hydroxy-coumarins and pyrones were regioselectively cyclized with N-bromosuccinimide (NBS) on solid phase under microwave irradiation in excellent yield. NBS on montmorillonite K-10 clay under microwave irradiation for expeditious solvent-free regioselective cyclization has been used for the first time.

引用

页码：1477 / 1484

页数：8

共 17 条

[1] FACTORS AFFECTING THE REGIOSELECTION OF THE ALLYLIC IMIDATES IODOCYCLIZATION [J].

BONGINI, A ;

CARDILLO, G ;

ORENA, M ;

SANDRI, S ;

TOMASINI, C .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (25) :4905-4910

[2] IODOCYCLOFUNCTIONALIZATION OF (Z)-1-TRICHLOROACETIMIDOYLOXYALK-2-ENES AND "3-TRICHLOROACETIMIDOYLOXYALK-1-ENES - SYNTHESIS OF (+/-)-ERYTHRO-SPHINGANINE TRIACETATE AND (+/-)-THREO-SPHINGANINE TRIACETATE [J].

BONGINI, A ;

CARDILLO, G ;

ORENA, M ;

SANDRI, S ;

TOMASINI, C .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (08) :1339-1344

[3] STEREOCONTROLLED CYCLOFUNCTIONALIZATIONS OF DOUBLE-BONDS THROUGH HETEROCYCLIC INTERMEDIATES [J].

CARDILLO, G ;

ORENA, M .

TETRAHEDRON, 1990, 46 (10) :3321-3408

[4] A NOVEL, EFFICIENT SYNTHESIS OF (+/-)-ERYTHRO-SPHINGOSINE [J].

CARDILLO, G ;

ORENA, M ;

SANDRI, S ;

TOMASINI, C .

TETRAHEDRON, 1986, 42 (03) :917-922

[5] C-ARYL GLYCOSIDES - ELECTROPHILE INITIATED CYCLIZATIONS OF 6-ARYL-5-HEXEN-2-OLS [J].

HART, DJ ;

LEROY, V ;

MERRIMAN, GH ;

YOUNG, DGJ .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (21) :5670-5680

[6] CARBAMATE MEDIATED FUNCTIONALIZATION OF UNSATURATED ALCOHOLS .2. REGIO-SELECTIVE AND STEREO-SELECTIVE SYNTHESIS OF 1,3-SYN AND 1,2-ANTI AMINO ALCOHOL DERIVATIVES VIA IODOCARBAMATION [J].

HIRAMA, M ;

IWASHITA, M ;

YAMAZAKI, Y ;

ITO, S .

TETRAHEDRON LETTERS, 1984, 25 (43) :4963-4964

[7] Synthesis of bioactive polyheterocycles: Regioselective cyclisation of 5-cyclohex-2-enyl-6-hydroxy[1]benzopyran-2-one [J].

Majumdar, KC ;

Chatterjee, P .

SYNTHETIC COMMUNICATIONS, 1998, 28 (19) :3633-3644

[8] SnCl4-I2 mediated regioselective 6-endo- and 5-exo-cyclization of ortho-allylenols [J].

Majumdar, KC ;

Biswas, A ;

Mukhopadhyay, PP .

CANADIAN JOURNAL OF CHEMISTRY, 2005, 83 (12) :2046-2051

[9] N-Iodosuccinimide -: An effective reagent for regioselective heterocyclization of o-cyclohex-2'-enylanilines for the synthesis of hexahydrocarbazoles [J].

Majumdar, KC ;

Kundu, UK ;

Das, U ;

Jana, NK ;

Roy, B .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 2005, 83 (01) :63-67

[10] N-iodosuccinimide:: An efficient reagent for regioselective heterocyclization of 3-allyl-4-hydroxy[1]benzopyran-2-ones [J].

Majumdar, KC ;

Basu, PK ;

Roy, B .

SYNTHETIC COMMUNICATIONS, 2003, 33 (20) :3621-3630

← 1 2 →