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Paper | Regular issue | Vol 85, No. 9, 2012, pp.2147-2171
Published online, 17th July, 2012
DOI: 10.3987/COM-12-12472
Microwave-Assisted Synthesis of 3,1-Benzoxazin-2-ones from 3-Hydroxyoxindoles

Oscar R. Suárez-Castillo,* Claudia I. Bautista-Hernández, Maricruz Sánchez-Zavala, Myriam Meléndez-Rodríguez, Araceli Sierra-Zenteno, Martha S. Morales-Ríos, and Pedro Joseph-Nathan

*Área Académica de Química, Universidad Autónoma del Estado de Hidalgo, Mineral de la Reforma, Hidalgo, 42184, Mexico

Abstract

A general protocol for the synthesis of 3,1-benzoxazin-2-ones 18 from 3-hydroxyoxindoles 16 in a two steps sequence through phenylsuccinates or phenylpropionates 17 is described. Best reaction conditions for ring opening of 16 to succinates or propionates 17 were achieved using alcohol/silica gel, while cyclization of 17 to benzoxazinones 18 was easily done with HCl/alcohol. It was also found that 17 and 18 can be transesterified using HCl/alcohol. Most transformations were carried out by traditional heating and by microwave (MW) irradiation to accelerate reaction rates.