Sequential one-pot synthesis of N-sulfonyl spiroaziridine oxindoles from spiroepoxy oxindoles

Abstract

The N-sulfonyl spiroaziridine oxindole is a recently developed versatile precursor in the synthesis of a wide range of 3,3-disubstituted spirooxindoles. It is usually prepared in three steps from isatin and needs costly and hardly available sulfinimides and hazardous peracid. A sequential and one-pot direct strategy for the synthesis of terminal N-sulfonyl spiroaziridine oxindoles has been developed under ambient conditions with excellent yields (up to 95%) from easily accessible spiroepoxy oxindoles by regioselective amination with aqueous ammonia and a subsequent ring enclosure reaction of the resulting 1,2-amino alcohol using easily available sulfonyl chloride and a base. Other salient features of the protocol include inexpensive substrate requirement and the ease of isolation of the desired product by performing single column chromatographic purification after two consecutive steps.