Synthesis of Selenium-Decorated <i>N</i>-Oxide Isoquinolines: Arylseleninic Acids in Selenocyclization Reactions

Abstract

High Resolution Image Download MS PowerPoint Slide 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- N -oxides through the selenocyclization of o -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 N -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).

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