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Access to Functionalized Isoquinoline N-Oxides via Sequential Electrophilic Cyclization/Cross-Coupling Reactions

✍ Scribed by Qiuping Ding; Jie Wu

Publisher: John Wiley and Sons
Year: 2008
Tongue: English
Weight: 202 KB
Volume: 350
Category: Article
ISSN: 1615-4150
DOI: 10.1002/adsc.200800301

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✦ Synopsis

Abstract

Electrophilic cyclization of 2‐alkynylbenzaldoximes with various electrophiles leads to the formation of 4‐iodoisoquinoline N‐oxides or 4‐bromoisoquinoline N‐oxides under mild conditions. The reaction can be transferred to highly functionalized isoquinoline N‐oxides via palladium‐catalyzed cross‐coupling reactions.

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## Abstract The reaction of 2‐alkynylbenzaldehydes with sulfonohydrazide and either bromine or iodine, followed by reaction with an aldehyde or ketone affords the corresponding bromo‐ or iodo‐substituted title compounds which undergo Suzuki—Miyaura cross‐coupling reactions.