REACTIONS OF CHLOROSULFONYLBENZYLIDENE HYDANTOINS

Abstract

Abstract 5-(Benzylidene- and o-chlorobenzylidene-) and cinnamylidene-hydantoins reacted with chlorosulfonic acid to give the corresponding p-sulfonyl chlorides (1, 35, 44). These were converted into 49 derivatives by reaction with amines, hydrazines and azide ion. 5-(o-chlorobenzylidene)hydantoin appeared to exist as two geometric isomers. The NMR spectra indicated that alkylation of the benzylidenehydantoins (3, 4, 38) occurred preferentially at the N(3)-position. The spectral data of the compounds are briefly discussed, together with preliminary biological screening results against insects, weeds and fungi.