Synthesis of 3-Substituted 2,1-Benzisoxazoles by the Oxidative Cyclization of 2-Aminoacylbenzenes with Oxone

Marco Chiarini; Luana Del Vecchio; Fabio Marinelli; Leucio Rossi; Antonio Arcadi

doi:10.1055/s-0035-1561471

Synthesis, Table of Contents

Synthesis 2016; 48(18): 3017-3030
DOI: 10.1055/s-0035-1561471

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Synthesis of 3-Substituted 2,1-Benzisoxazoles by the Oxidative Cyclization of 2-Aminoacylbenzenes with Oxone

Marco Chiarini

^aFacoltà di Bioscienze e Tecnologie Agroalimentari e Ambientali, Università di Teramo, Via Carlo Lerici 1, 64023 Mosciano Sant’Angelo (Te), Italy

,

Luana Del Vecchio

^bDipartimento di Scienze Fisiche e Chimiche, Università di L’Aquila, Via Vetoio, 67010 Coppito (AQ), Italy Email: antonio.arcadi@univaq.it

,

Fabio Marinelli

^bDipartimento di Scienze Fisiche e Chimiche, Università di L’Aquila, Via Vetoio, 67010 Coppito (AQ), Italy Email: antonio.arcadi@univaq.it

,

Leucio Rossi

^bDipartimento di Scienze Fisiche e Chimiche, Università di L’Aquila, Via Vetoio, 67010 Coppito (AQ), Italy Email: antonio.arcadi@univaq.it

,

Antonio Arcadi*

^bDipartimento di Scienze Fisiche e Chimiche, Università di L’Aquila, Via Vetoio, 67010 Coppito (AQ), Italy Email: antonio.arcadi@univaq.it

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Abstract

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Abstract

An efficient approach to the synthesis of 2,1-benzisoxazoles through direct construction of the N–O bond by the chemoselective oxidation of 2-aminoacylbenzenes with Oxone is described. This alternative methodology is characterized by its simple and transition-metal-free conditions and good functional group compatibility utilizing Oxone as a green oxidant instead of hypervalent iodine compounds. Moreover, this new procedure simplifies the number of steps compared to the previously reported procedure by circumventing the use of 2-azido-substituted aryl ketones.

Key words

Oxone - 2,1-benzisoxazoles - 2-aminoacylbenzenes - oxidative cyclization - transition-metal-free

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References

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