Unexpected hydrazine- and hydroxylamine-induced transformations of aza-14-crown-4 incorporating 4-oxopiperidine-3-carboxylate moiety

Reactions of aza-14-crown-4 incorporating 4-oxopiperidine-3-carboxylate moiety with hydrazine and hydroxylamine proceed at the functional groups. One unexpected product, cyclopenteno-13-crown-3 ether derivative, is formed when hydrazine hydrochloride is used, its formation occurring via deamination of the piperidine followed by the Nazarov reaction of the intermediate hydrazono diene. According to the QSAR through ADMET calculation, the synthesized compounds may show high potential for biological studies.