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3-Heterosubstituted Benzofurans from Hydroxyphenyl Propargyl Alcohols via ortho-Quinone Methide through a Metal-/Catalyst-Free Conjugate Addition/Oxy-Cyclization
ACS Omega ( IF 4.1 ) Pub Date : 2018-12-12 00:00:00 , DOI: 10.1021/acsomega.8b02480
Manda Rajesh 1, 2 , Maneesh Kumar Reddy Singam 1, 2 , Ranjith Kumar Gadi 1, 2 , Maddi Sridhar Reddy 1, 2
Affiliation  

A facile route to 3-sulfonylated and 3-(1-benzotriazolyl)-benzofurans is achieved from readily available o-hydroxyphenyl propargyl alcohols (o-HPPAs) and bench-top sodium sulfonylates and benzotriazoles with no assistance of any reagent or catalyst. Bifunctional o-quinone methides (o-QMs) were the putative reaction intermediates ensued from dehydration of o-HPPA. Our study revealed that the o-QM was so choosy in selection of the nucleophiles for the key Michael addition reaction.

中文翻译:

通过苯二甲酰亚胺通过无金属/无催化剂的共轭加成/氧环化反应,从苯二甲炔丙醇中制得3-杂取代的苯并呋喃

一种简便路线3-磺酰化和3-(1-苯并三唑基)-benzofurans从容易获得实现ö羟基苯基炔丙基醇(Ò -HPPAs)和台式钠sulfonylates和苯并三唑无任何试剂或催化剂的协助。双功能醌甲基化物(o -QMs)是o -HPPA脱水产生的推定反应中间体。我们的研究表明,对于关键的迈克尔加成反应,在选择亲核试剂时,o -QM是如此挑剔。
更新日期:2018-12-12
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