Green Synthesis of New Boron-Containing Quinazolines: Preparation of Benzo[d][1,3,2]diazaborinin-4(1H)-one Derivatives

Author: Mahdavi Mohammad   Asadi Mehdi   Saeedi Mina   Tehrani Maryam Hosseinpour   Mirfazli Seyedeh Sara   Shafiee Abbas   Foroumadi Alireza  

Publisher: Taylor & Francis Ltd

ISSN: 0039-7911

Source: Synthetic Communications, Vol.43, Iss.21, 2013-11, pp. : 2936-2942

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Abstract

A series of new boron-containing quinazolinones, benzo[d][1,3,2]diazaborinin-4(1H)-one derivatives, were synthesized by the sequential one-pot reaction of isatoic anhydride, amines, and arylboronic acids in the absence of a catalyst and solvent. Heating isotoic anhydride and amines led to the formation of 2-aminobenzamide intermediates, which reacted easily with boronic acids to obtain the title compounds in good yields. Solvent-free conditions provided a unique procedure because the corresponding products were not obtained using various solvents either under reflux conditions or at room temperature.[Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource: Full experimental and spectral details.]

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