Chemistry of allene sulfoxides: a new synthesis of 1-aryl-3,4-dihydro-1H-[1]benzothieno[3,2-c]pyrans

被引:5
作者
Edwards, N
Macritchie, JA
Parsons, PJ
Drew, MGB
Jahans, AW
机构
[1] UNIV READING,DEPT CHEM,XRAY CRYSTALLOG LAB,READING RG6 2AD,BERKS,ENGLAND
[2] AGREVO UK LTD,SAFFRON WALDEN CB10 1XL,ESSEX,ENGLAND
关键词
D O I
10.1016/S0040-4020(97)00786-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel synthesis of 1-aryl-3,4-dihydro-1H-[1]benzothieno[3,2-c]pyrans has been developed, utilising the acid-catalysed cyclisation of 5,6-dihydro-4-phenylsulfinyl-2H-pyrans. Both ring systems could be isolated from suitably substituted allene sulfoxides upon exposure to p-toluenesulfonic acid in refluxing tetrahydrofuran, the nature of the product depending on the reaction time. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:12651 / 12660
页数:10
相关论文
共 16 条
[1]   PHOSPHOR AND SULFURIC-ACID SUBSTITUTED ALLENES .4. A SIMPLE SYNTHESIS OF 2[5H]FURANONES AND "BETA-METHYLENE-GAMMA-BUTYROLACTONES BY ADDITION OF MALONIC-ACID ESTERS TO ALLENIC SULFOXIDES [J].
ALTENBACH, HJ ;
SOICKE, H .
TETRAHEDRON LETTERS, 1986, 27 (14) :1561-1562
[2]  
BARRETT AGM, 1990, ORG SYNTH, V68, P8
[3]   THIANAPHTHEN-2-ONE CHEMISTRY .1. SYNTHESIS OF 6H-BENZOTHIENO[3,2-C][1]BENZOPYRAN-6-ONES (11-THIACOUMESTANS) [J].
CONLEY, RA ;
HEINDEL, ND .
JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (22) :3169-3173
[4]   PROTECTION OF HYDROXYL GROUPS AS TERT-BUTYLDIMETHYLSILYL DERIVATIVES [J].
COREY, EJ ;
VENKATESWARLU, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (17) :6190-+
[5]   PYRANO HETEROCYCLES .1. SYNTHESES OF ISOCHROMANS AND NOVEL THIENO[3,2-C]PYRAN, BENZOTHIENO[3,2-C]PYRAN, BENZOTHIENO[2,3-C]PYRAN AND PYRANO[4,3-B]BENZOFURAN SYSTEMS [J].
DOBSON, TA ;
HUMBER, LG .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1975, 12 (03) :591-594
[6]   AN ENANTIOSELECTIVE CENTRAL AXIAL CENTRAL CHIRAL ELEMENT TRANSFER PROCESS LEADING TO A CONCISE SYNTHESIS OF (+)-STERPURENE - INTRAMOLECULAR DIELS-ALDER REACTIONS OF VINYLALLENE SULFOXIDES [J].
GIBBS, RA ;
BARTELS, K ;
LEE, RWK ;
OKAMURA, WH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (10) :3717-3725
[7]  
GRAY M, 1992, SYNLETT, P597
[8]  
GRAY M, 1993, SYNLETT, P281
[9]  
HORNER L, 1972, LIEBIGS ANN CHEM, V757, P33