腈
位阻效应
醛
反应性(心理学)
化学
组合化学
冷凝
有机化学
药物化学
催化作用
医学
热力学
物理
病理
替代医学
作者
Michał Pieczykolan,Bartłomiej Sadowski,Daniel T. Gryko
标识
DOI:10.1002/anie.201915953
摘要
Abstract A new, transformative methodology for the preparation of diketopyrrolopyrroles from aldehydes, primary amines, nitriles, and diethyl oxalacetate has been developed. It is now possible to prepare diketopyrrolopyrroles bearing an ordered arrangement of three different substituents from abundant and commercially available materials, allowing the independent regulation of all desired physicochemical properties. For the first time very electron‐rich (carbazol‐3‐yl, dimethylaminophenyl, pyrrolo[3,2‐ b ]pyrrolyl), and sterically hindered substituents (naphthalen‐1‐yl, quinolin‐4‐yl, acridin‐9‐yl, imidazo[1,5‐ a ]pyridin‐1‐yl, 2‐bromophenyl etc.) can be appended to the diketopyrrolopyrrole core by condensation of an appropriate nitrile with a pyrrolidin‐2‐one intermediate. Even greater synthetic possibilities are related to the fact that such demanding substituents as 4‐dimethylaminophenyl, indol‐3‐yl, and 2‐methoxyphenyl can be incorporated from aldehyde precursors, bypassing problems with the nitriles reactivity.
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