Dimethylaminomethylene derivatives of S,S-dioxides of 1,4-benzothiazepin-3(2H)-one and 4,1-benzothiazepin-2(3H)-one: comparison of interaction with nucleophiles

Reactions of dimethylaminomethylene derivatives of 4,5-dihydro-1,4-benzothiazepin-3(2 H )-one 1,1-dioxide and 1,5-dihydro-4,1-benzothiazepin-2(3 H )-one 4,4-dioxide with O-nucleophile (hydroxide ion) and N-nucleophiles (aliphatic and aromatic amines, hydroxylamine, hydrazine, phenylhydrazines, N , N -dimethylhydrazine, amidines, and esters of amino acids) have been investigated. Compounds with a carbonyl group or a hydrogen at the nitrogen atom of the 1,4-benzothiazepine cycle are more reactive than N -Me derivatives. Products of transamination of 4,1-benzothiazepine derivatives have not been obtained, but hydrolysis led to the corresponding enol or 1,1-diol. Graphical Abstract