硒修饰的氧化异喹啉的合成：硒环化反应中的芳基硒酸

Anghinoni João M, Ferreira Sabrina S, Kazmierczak Jean C, Perin Gelson, Penteado Filipe, Lenardão Eder J

Centro de Ciências Químicas, Farmacêuticas e de Alimentos (CCQFA), Universidade Federal de Pelotas (UFPel), P.O. Box 354, Pelotas, 96010-900 Rio Grande do Sul, Brazil.

Centro de Ciências Exatas e Naturais, Departamento de Química, Universidade Federal de Santa Maria (UFSM), Av. Roraima, Building 18, Santa Maria, 97105-340 Rio Grande do Sul, Brazil.

J Org Chem. 2024 Aug 16;89(16):11272-11280. doi: 10.1021/acs.joc.4c00944. Epub 2024 Aug 1.

Herein, we describe the use of benzeneseleninic acid derivatives (BSA) as a bench-stable and easy to handle selenium reagent to access 4-(selanyl)isoquinoline--oxides through the selenocyclization of -alkynyl benzaldehyde oximes. The reaction is conducted in refluxing methanol, allowing the thermal generation of electrophilic selenium species in situ. By this new protocol, a library of 19 selenium-decorated -oxide isoquinolines was accessed in up to 96% yield with an outstanding substrate tolerance and the feasibility to scale it up 10 times (from 0.25 to 2.5 mmol).

在此，我们描述了使用苯硒酸衍生物（BSA）作为一种易于保存且易于操作的硒试剂，通过α-炔基苯甲醛肟的硒环化反应来制备4-(硒基)异喹啉氧化物。该反应在回流的甲醇中进行，可原位热生成亲电硒物种。通过这一新方法，获得了一个包含19种硒修饰的异喹啉氧化物的文库，产率高达96%，底物耐受性良好，并且具有扩大10倍规模（从0.25 mmol扩大到2.5 mmol）的可行性。