Synthesis of Thieno-Fused Heterocycles through Reiterative Iodocyclization

被引：39

作者：

Aurelio, Luigi ^{[1
]}

Volpe, Rohan ^{[1
]}

Halim, Rosliana ^{[1
]}

Scammells, Peter J. ^{[1
]}

Flynn, Bernard L. ^{[1
]}

机构：

[1] Monash Univ, Monash Inst Pharmaceut Sci, Parkville, Vic 3052, Australia

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2014年 / 356卷 / 09期

关键词：

cyclization; iodocyclization; sulfur heterocycles; synthetic methods; ELECTROPHILIC CYCLIZATION; REACTION CASCADES; TERMINAL ALKYNES; OLIGOTHIOPHENES; THIOPHENE; IODINE; QUINOLINES; ANALOGS; DESIGN;

D O I：

10.1002/adsc.201400072

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Iodocyclization of ethynyl methyl sulfides gives 3-iodo-2-thiomethyl heterocycles, setting up the synthesis of thieno-fused systems through a subsequent iteration of alkyne coupling and iodocylization. This approach can also be exploited in the synthesis of polyfused thiophenes. In developing this protocol it was necessary to address issues associated with unfavourable electronic bias and redox sensitivity in some substrates. The manner in which these have been addressed should prove useful elsewhere in iodocyclization chemisty.

引用

页码：1974 / 1978

页数：5

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