Synthesis of Fused 4-Iodoselenophene[2,3-b]thiophenes by Electrophilic Cyclization of 3-Alkynylthiophenes

被引：20
|
作者：
Stein, Andre L. [2 ]
da Rocha, Juliana [2 ]
Menezes, Paulo Henrique [1 ]
Zeni, Gilson [1 ]
机构：
[1] Univ Fed Pernambuco, Dept Quim Fundamental, BR-50670901 Recife, PE, Brazil
[2] Univ Fed Santa Maria, CCNE, Lab Sintese Reatividade Avaliacao Farmacol & Toxi, BR-97105900 Santa Maria, RS, Brazil
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 2010卷 / 04期
关键词：
Fused-ring systems; Sulfur heterocycles; Cyclization; Cross-coupling; Alkynes; Chalcogens; IN-VITRO; THIOPHENE; ANALOGS; 2-BETA-D-RIBOFURANOSYLSELENAZOLE-4-CARBOXAMIDE; SELENOPHENES; DERIVATIVES; TIAZOFURIN; ALKYNES;
D O I：
10.1002/ejoc.200901118
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We present here our results on the electrophilic cyclization reaction of 3-alkynylthiophenes with different electrophiles such as I-2, ICl, and PhSeBr. The cyclization reaction proceeded cleanly under mild reaction conditions, giving fused 4-iodoselenophene[2,3-b]thiophenes in excellent yields. In addition, the obtained chalcogenophenes were readily transformed into more complex product, through palladium- or copper-catalyzed cross-coupling reactions with thiols, boronic acids, and organozinc reagents.
引用
收藏
页码：705 / 710
页数：6
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