Abstract
A general protocol for the synthesis of 3,l-benzoxazin-2-ones 18 from 3-liydroxyoxindoles 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.
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