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Direct Use of Benzylic Alcohols for Multicomponent Synthesis of 2‐Aryl Quinazolinones Utilizing the π‐Benzylpalladium(II) System in Water by Hidemasa Hikawa; Taku Nakayama; Makiko Takahashi; Shoko Kikkawa; Isao Azumaya is a Chemistry article available to read on EtoBox.

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## Abstract We demonstrate the direct use of benzylic alcohols for a multicomponent reaction of readily available isatoic anhydrides with amines in water, which is a synthetic route for the direct construction of a series of 2‐aryl quinazolinones. This one‐pot synthetic method involves the dehydrative N‐benzylation of in situ generated anthranilamides followed by an amide‐directed benzylic C−H amination process utilizing the π‐benzylPd(II) system. Comparison of independent rate measurements using benzyl alcohol and its deuterated form gave a kinetic isotope effect of 3.5. Therefore, the benzylic C−H bond is cleaved in the rate‐determining step. We successfully carried out a gram‐scale reaction in 85% yield with simplified product isolation. magnified image

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Author

Hidemasa Hikawa; Taku Nakayama; Makiko Takahashi; Shoko Kikkawa; Isao Azumaya

Publisher

Wiley

Published

2021

Language

EN

Field

Chemistry (Physical Sciences)