SYNTHESIS OF N-(8-METHOXY-5-QUINOLYLSULFONYL)AZIRIDINE AND ITS REACTIONS WITH SECONDARY AMINES. PMR SPECTRA AND STRUCTURES OF THE DERIVATIVES OBTAINED

Article abstract of DOI:10.1007/BF00519816

A method for the synthesis of a new fluorescent derivative of ethyleneimine, viz., N-(8-methoxy-5-quinolylsulfonyl)-aziridine, starting from 8-methoxyquinoline-5-sulfonyl chloride was developed.The quinolylsulfonylaziridine reacts smoothly with secondary aliphatic amines to give 8-methoxy-5-quinolinesulfonamides.In a study of the PMR spectra of these compounds it was established that significant deshielding of the 4-H proton (0.8 ppm) and a substantial increase (by 0.8 ppm) in ³J_(6,7) are characteristic signs of the introduction of aziridinylsulfonyl or N-(2-N-dialkylamino)sulfonamido substituents into the 5 position of 8-methoxyquinoline.