Synthesis 2016; 48(18): 3017-3030
DOI: 10.1055/s-0035-1561471
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© Georg Thieme Verlag Stuttgart · New York

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

Marco Chiarini
a  Facoltà di Bioscienze e Tecnologie Agroalimentari e Ambientali, Università di Teramo, Via Carlo Lerici 1, 64023 Mosciano Sant’Angelo (Te), Italy
,
Luana Del Vecchio
b  Dipartimento di Scienze Fisiche e Chimiche, Università di L’Aquila, Via Vetoio, 67010 Coppito (AQ), Italy   Email: antonio.arcadi@univaq.it
,
Fabio Marinelli
b  Dipartimento di Scienze Fisiche e Chimiche, Università di L’Aquila, Via Vetoio, 67010 Coppito (AQ), Italy   Email: antonio.arcadi@univaq.it
,
Leucio Rossi
b  Dipartimento di Scienze Fisiche e Chimiche, Università di L’Aquila, Via Vetoio, 67010 Coppito (AQ), Italy   Email: antonio.arcadi@univaq.it
,
Antonio Arcadi*
b  Dipartimento di Scienze Fisiche e Chimiche, Università di L’Aquila, Via Vetoio, 67010 Coppito (AQ), Italy   Email: antonio.arcadi@univaq.it
› Author Affiliations
Further Information

Publication History

Received: 11 April 2016

Accepted after revision: 03 May 2016

Publication Date:
22 June 2016 (online)


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.

Supporting Information

 
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