DBU催化的炔基亚胺酯环化反应合成1-烷氧基吡嗪并[1,2-a]吲哚
DBU-Catalyzed Alkyne-Imidate Cyclization toward 1-Alkoxypyrazino[1,2- a]indole Synthesis.
作者信息
Festa Alexey A, Zalte Rajesh R, Golantsov Nikita E, Varlamov Alexey V, Van der Eycken Erik V, Voskressensky Leonid G
机构信息
Peoples' Friendship University of Russia (RUDN University) , Miklukho-Maklaya Street 6 , Moscow 117198 , Russian Federation.
Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry , University of Leuven (KU Leuven) , Celestijnenlaan 200F , B-3001 Leuven , Belgium.
出版信息
J Org Chem. 2018 Aug 17;83(16):9305-9311. doi: 10.1021/acs.joc.8b01279. Epub 2018 Jul 19.
1-(Propargyl)indol-2-carbonitriles react with alcohols to afford 1-alkoxypyrazino[1,2- a]indoles under DBU-catalyzed microwave-assisted conditions. The reaction scope includes a wide range of indoles, primary and secondary alcohols, and a thiol. The initial mechanistic study shows that the domino process presumably proceeds through an alkyne-allene rearrangement, imidate formation, and nucleophilic cyclization reaction sequence.
1-（炔丙基）吲哚-2-腈在DBU催化的微波辅助条件下与醇反应，生成1-烷氧基吡嗪并[1,2-a]吲哚。反应范围包括多种吲哚、伯醇和仲醇以及一种硫醇。初步机理研究表明，多米诺过程可能通过炔烃-丙二烯重排、亚胺酯形成和亲核环化反应序列进行。
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