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Abstract
The dipolar cycloadducts from diaryl azines and maleimides (1, 20) or maleic anhydride (18) have been reacted with chlorosulfonic acid to give the bis- (2, 19) or tetrachlorosulfonyl derivatives (21). The chorosulfonation generally required addition of thionyl chloride. The various sulfonyl chlorides were converted into a range of sulfonamides (3-11, 13-16) and the N-butylsulfamate (12). The N,N-dialkylsulfamonyl cycloadducts (23, 25) were also obtained by cycloaddition of the bis-dimethylsulfamoyl 2-methoxybenzaldehyde azine (22) and N-phenyl maleimide or the N-(p-diethylsulfamoylphenyl) maleimide (24) with p-tolualdehyde azine, although the former reaction did not go to completion.
Attempts to carry out the cycloaddition between the two sulfamoyl reactants (22 and 24) were unsuccessful. The various sulfonamide derivatives will be screened as pesticides.