CYCLOTHIOMETHYLATION OF PRIMARY AMINES WITH FORMALDEHYDE AND AROMATIC DITHIOLS – AN EFFECTIVE METHOD FOR THE SYNTHESIS OF CYCLOPHANES

Abstract

An effective method has been developed for the synthesis of S,N- and S,N,O-containing cyclophanes by cyclothiomethylation reaction of primary amines with formaldehyde and aromatic dithiols. Benzene-1,2-dithiols were used in [1+2+1] cyclocondensation reaction that gave N-substituted 1,5,3-benzodithiazepines, while benzene-1,4-dithiol and 4,4'-dimercaptodiphenyl oxide participated in a [3+6+3] cyclocondensation reaction leading to cyclophanes.