化学
原子经济
异构化
试剂
催化作用
羟醛反应
级联
氨
立体中心
原位
有机化学
一锅法合成
重组
组合化学
对映选择合成
色谱法
财务
经济
作者
Alagesan Balasubramani,Anilkumar Gunnam,Goverdhan Mehta
标识
DOI:10.1021/acs.joc.2c01089
摘要
One-pot synthesis of 2-azaflorenones from readily accessed o-bis-ynones through Michael addition, orthogonal aldol reaction, dehydrative isomerization, and a 6-endo-dig-cyclization cascade, triggered by in situ-generated ammonia in the presence of a Cu(I) catalyst, has been discovered and its generality scoped. A few selected reactions of a prototypical 2-azafluorenone have been explored for functionality augmentation in its core structure. Overall, this operationally convenient 2-azafluorenone synthesis involves the formation of five new bonds (3 C–N and 2 C–C) in one pot and embodies many green and sustainable features; notably, the reagent ammonia is subsumed into the reactant o-bis-ynones with atom economy, and the only by-product is water.
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