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

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.

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GRAPHICAL ABSTRACT

Keywords:

• 2-Aminobenzamides
• boron-containing quinazolines
• boronic acids
• isatoic anhydride
• solvent-free

ACKNOWLEDGMENTS

This research was supported by grants from the Research Council of Tehran University of Medical Sciences and Iran National Science Foundation (INSF).

Notes

^a Isolated yields, and compounds 4b–4k are new.