Redox-Neutral and Atom-Economic Route to β-Carbolines via Gold-Catalyzed [4+2] Cycloaddition of Indolylynamides and Cyanamides

被引：15
|
作者：
Shcherbakov, Nikolay, V [1 ]
Chikunova, Elena, I [1 ]
Dar'in, Dmitry [1 ]
Kukushkin, Vadim Yu [1 ,2 ]
Dubovtsev, Alexey Yu [1 ]
机构：
[1] St Petersburg State Univ, St Petersburg 199034, Russia
[2] Altai State Univ, Inst Chem & Pharmaceut Technol, Barnaul 656049, Russia
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 24期
基金：
俄罗斯科学基金会;
关键词：
DIELS-ALDER CYCLOADDITION; INDUSTRIAL PERSPECTIVE; COUNTER ANIONS; YNAMIDES; CYCLIZATION; REGIOSELECTIVITY; REACTIVITY; REVERSAL;
D O I：
10.1021/acs.joc.1c02119
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Gold(I)-catalyzed [4 + 2] cycloaddition of indolylynamides and cyanamides (aminonitriles) is an efficient redox-neutral and atom-economic route to diversely substituted 1,3-diamino-beta-carbolines. The protocol operates under mild conditions (Ph3PAuNTf2 5 mol %, DCE, 60 degrees C) with a good tolerance to functional groups (23 examples and yields up to 98%). The obtained beta-carboline systems represent a versatile synthetic platform with modifiable substituents for successive functionalizations. Control experiments indicate the crucial role of both the nature of reactants and the identity of employed catalysts in the developed cycloaddition.
引用
收藏
页码：17804 / 17815
页数：12
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