N-芳基-1-氧代-1H-异吲哚鎓离子与叔烯酰胺的 Aza-Diels-Alder 反应：反应结果的立体效应。
Aza-Diels-Alder reaction between N-aryl-1-oxo-1H-isoindolium ions and tert-enamides: Steric effects on reaction outcome.
机构信息
Department of Chemistry, Acadia University, Wolfville, NS, Canada.
Department of Chemistry, Dalhousie University, Halifax, NS, Canada.
出版信息
Beilstein J Org Chem. 2014 Apr 14;10:848-57. doi: 10.3762/bjoc.10.81. eCollection 2014.
The synthesis of 5-substituted 6,6a-dihydroisoindolo[2,1-a]quinolin-11(5H)-ones via [4 + 2] imino-Diels-Alder cyclization from N-aryl-3-hydroxyisoindolinones and N-vinyl lactams under Lewis acid-catalysed anhydrous conditions is reported. Reactions of N-(2-substituted-aryl)-3-hydroxyisoindolinones with N-vinylpyrrolidone under identical conditions resulted in the formation of 2-(2-substitued-aryl)-3-(2-(2-oxopyrrolidin-1-yl)vinyl)isoindolin-1-one analogues indicating steric hinderance as the cause of deviation. The probable mechanism of the reaction based on the results from X-ray crystallography and molecular modelling is discussed.
本文报道了在路易斯酸催化的无水条件下，通过 N-芳基-3-羟基异吲哚啉酮和 N-乙烯基内酰胺的[4+2]亚胺-Diels-Alder 环化反应合成 5-取代的 6,6a-二氢异吲哚并[2,1-a]喹啉-11(5H)-酮。在相同条件下，N-(2-取代芳基)-3-羟基异吲哚啉酮与 N-乙烯基吡咯烷酮的反应生成了 2-(2-取代芳基)-3-(2-(2-氧代吡咯烷-1-基)乙烯基)异吲哚啉-1-酮类似物，表明空间位阻是偏离的原因。根据 X 射线晶体学和分子建模的结果，讨论了反应的可能机制。
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