Metal‐Free Synthesis of Anthranils by PhIO Mediated Heterocyclization of ortho‐Carbonyl Anilines

Abstract

Here, we report a metal‐free synthesis of anthranils from ortho‐carbonyl anilines using PhIO as a sole additive under ambient conditions. This methodology did not require any external additives and delivered anthranils in excellent yields with broad substrate scope. The mechanistic studies suggest that the reaction proceeds via in‐situ generation of iminoiodane leading to nitrene and a subsequent nucleophilic attack from oxygen of ortho‐carbonyl aniline on nitrene results in heterocyclization.

Updates on hypervalent-iodine reagents: metal-free functionalisation of alkenes, alkynes and heterocycles

“…The mechanistic investigation suggests the involvement of a nitrene intermediate giving the desired product with good functional group compatibility (Scheme 36). 95…”

“…The mechanistic investigation suggests the involvement of a nitrene intermediate giving the desired product with good functional group compatibility (Scheme 36). 95 As per the proposed mechanism, an intermediate (A) is generated via the interaction of a Lewis base ( 59 The benzoxazin-2-one nucleus represents a unique class of lactone compounds that exhibits outstanding biological and pharmacological activities. 96 In this regard, Chen et al reported the synthesis of benzoxazin-2-ones ( 62) via oxidative C-H annulation reaction of arylamines ( 61) with α-keto acids.…”

Rh(III)-Catalyzed Tandem Reaction Access to (Quinazolin-2-yl)methanone Derivatives from 2,1-Benzisoxazoles and α-Azido Ketones

“…2,1-Benzisoxazoles 1 were prepared according to the literature procedure . Other substrates and reagents were commercial and used without further purification.…”

Subnanometric Pt clusters supported on MgO-incorporated porous carbon as efficient metal–base bifunctional catalysts for reductive heterocyclization reactions

“…2,1-Benzisoxazoles and related N-heterocyclic compounds (also known as anthranils) are important starting materials for the synthesis of pharmaceutical intermediates, organic functional materials, and industrial surfactants. [1][2][3][4][5][6] For instance, anthranil derivatives are applied to treat several central nervous system abnormalities, 7,8 act as anti-inflammatory drugs, 9,10 and can be used to produce antiplatelet inhibitors, quinolinones, and acridone. [11][12][13][14] Due to fundamental significance and practical values of these compounds, several protocols have been developed for their synthesis.…”