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Oxidative cyclization of allyl compounds and isocyanide: A facile entry to polysubstituted 2-cyanopyrroles
Chinese Chemical Letters ( IF 9.4 ) Pub Date : 2023-07-26 , DOI: 10.1016/j.cclet.2023.108836
Yaping Zhang , Wei Zhou , Mingchun Gao , Tianqi Liu , Bingxin Liu , Chang-Hua Ding , Bin Xu

A facile TfOH-catalyzed oxidative cyclization of allyl compounds and isocyanide has been developed with the assistance of DDQ, where isocyanide is used as the crucial "N" and "CN" sources. Highly functionalized 2-cyanopyrroles are constructed efficiently through a new formal [3 + 2] mode, demonstrating diverse reactivity and synthetic utility in organic chemistry. 2-Cyanopyrrole is converted into a nucleobase analogue of Remdesivir and 5-pyrrolo[2,1-]isoindole through a three-step or a two-step sequence, respectively. This protocol features broad substrate scope, operational simplicity and good functional group tolerance.

中文翻译:

烯丙基化合物和异氰化物的氧化环化:轻松获得多取代的 2-氰基吡咯

在DDQ的帮助下,开发了一种简便的TfOH催化烯丙基化合物和异氰化物的氧化环化反应,其中异氰化物被用作关键的“N”和“CN”源。通过新的形式[3 + 2]模式有效构建高度功能化的2-氰基吡咯,在有机化学中表现出多种反应性和合成实用性。 2-氰基吡咯分别通过三步或两步序列转化为瑞德西韦和5-吡咯并[2,1-]异吲哚的核碱基类似物。该方案具有底物范围广、操作简单和良好的官能团耐受性等特点。
更新日期:2023-07-26
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