Butadienic building blocks from 2-nitrothiophene as precursors of nitrogen heterocycles: Intriguing dichotomic behavior

被引：12
作者：
Bianchi, Lara
Giorgi, Gianluca
Maccagno, Massimo
Petrillo, Giovanni
Rocca, Valeria
Sancassan, Fernando
Scapolla, Carlo
Severi, Elda
Tavani, Cinzia
机构：
[1] Univ Genoa, Dipartimento Chim & Chim Ind, I-16146 Genoa, Italy
[2] Univ Siena, Dipartimento Chim, I-53100 Siena, Italy
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 24期
关键词：
D O I：
10.1021/jo701460k
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[Graphics] With the goal of their exploitation for the synthesis of heterocycles, sulfides 10 and sulfones 11, derived from the initial ring-opening of 2-nitrothiophene (5) with pyrrolidine/AgNO3 in EtOH, were reacted with diazomethane. Interesting dichotomic behavior was found to yield pyrazolines 17 from 10 and isoxazolines 18 (as the main products) from 11. Intriguingly enough, in the latter case, an unexpected apparent C-C methylene insertion was also observed, leading to the homologous cyclopropanes 19 as secondary products.
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页码：9067 / 9073
页数：7
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