Synthesis of thienothiopyranthiones by a new molecular rearrangement

被引：16

作者：

Ogurtsov, VA

Rakitin, OA

Rees, CW

Smolentsev, AA

Belyakov, PA

Golovanov, DG

Lyssenko, KA

机构：

[1] Russian Acad Sci, ND Zelinskii Organ Chem Inst, Moscow 119991, Russia

[2] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England

[3] Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 119991, Russia

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 05期

关键词：

D O I：

10.1021/ol0476669

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

On heating with alkynes, the readily prepared 1,3-dithioles 3 undergo a new cycloaddition reaction and an unprecedented molecular rearrangement with loss of chlorine to give the first 7H-thieno[2,3-c]thiopyran-7-thiones 4 and 4H-thieno[3,2-c]thiopyran-4-thiones 5 whose structures were confirmed by X-ray diffraction. Unexpectedly, the different alkynes used to form 3 and to convert it into 4 and 5 were incorporated regiospecifically into the thiophene and thiopyran rings, respectively.

引用

页码：791 / 794

页数：4

共 27 条

[1] DITHIAINDENES - SYNTHESIS OF 6-THIA-7H-BENZO [B] THIOPHENE (1,6-DITHIAINDENE) AND 1,3-DIMETHYL-5-THIA-4H-BENZO [C] THIOPENE (1,3-DIMETHYL-2,5-DITHIAINDENE) AND ATTEMPTED SYNTHESIS OF 5-THIA-4H-BENZO [B] THIOPHENE (1,5-DITHIAINDENE) [J].