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The intramolecular reaction of acetophenone N-tosylhydrazone and vinyl: Brønsted acid-promoted cationic cyclization toward polysubstituted indenes
Chemical Communications ( IF 4.9 ) Pub Date : 2021-1-15 , DOI: 10.1039/d0cc07966a
Zhixin Wang 1, 2, 3, 4 , Yang Li 1, 2, 3, 4 , Fan Chen 4, 5, 6, 7, 8 , Peng-Cheng Qian 4, 5, 6, 7, 8 , Jiang Cheng 1, 2, 3, 4, 5
Affiliation  

In the presence of TsNHNH2, a Brønsted acid-promoted intramolecular cyclization of o-(1-arylvinyl) acetophenone derivatives was developed, leading to polysubstituted indenes with complexity and diversity in moderate to excellent yields. In sharp contrast with either the radical or carbene involved cyclization of aldehydic N-tosylhydrazone with vinyl, a cationic cyclization pathway was involved, where N-tosylhydrazone served as an electrophile and alkylation reagent during this transformation.

中文翻译:

苯乙酮N-甲苯磺酰and与乙烯基的分子内反应:布朗斯台德酸促进阳离子环化成多取代茚

在存在TsNHNH 2的情况下,开发了布朗斯台德酸促进的-(1-芳基乙烯基)苯乙酮衍生物的分子内环化反应,导致多取代的茚并酮具有复杂性和多样性,产率中等至优异。与自由基或卡宾涉及醛基N-甲苯磺酰hydr与乙烯基的环化形成鲜明对比,涉及阳离子环化途径,其中N-甲苯磺酰zone在该转化过程中用作亲电试剂和烷基化试剂。
更新日期:2021-01-22
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