一锅两步级联合成喹唑啉并三氮唑苯并二氮杂卓。
One-pot, two-step cascade synthesis of quinazolinotriazolobenzodiazepines.
机构信息
Department of Chemistry, University of California , One Shields Avenue, Davis, California 95616, United States.
出版信息
Org Lett. 2012 Jul 20;14(14):3732-5. doi: 10.1021/ol301592z. Epub 2012 Jun 29.
Abstract
An operationally simple, one-pot, two-step cascade method has been developed to afford quinazolino[1,2,3]triazolo[1,4]benzodiazepines. This unique, atom-economical transformation engages five reactive centers (amide, aniline, carbonyl, azide, and alkyne) and employs environmentally benign iodine as a catalyst. The method proceeds via sequential quinazolinone-forming condensation and intramolecular azide-alkyne 1,3-dipolar cycloaddition reactions. Substrate scope, multicomponent examples, and mechanistic insights are discussed.
摘要
已经开发出一种操作简单、一锅两步级联方法，以提供喹唑啉并[1,2,3]三唑并[1,4]苯并二氮杂卓。这种独特的、原子经济的转化涉及五个反应中心（酰胺、苯胺、羰基、叠氮化物和炔烃），并采用环境友好的碘作为催化剂。该方法通过顺序的喹唑啉酮形成缩合和分子内叠氮化物-炔烃 1,3-偶极环加成反应进行。讨论了底物范围、多组分实例和反应机理的见解。
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