SYNTHESIS OF NOVEL DIPYRIDO-1,4-THIAZINES

摘要

An efficient synthesis of novel type of dipyrido-1,4-thiazine (4)was elaborated in the reactions of two pairs of 3,4-disubstituted pyridines in DMF.The reactions proceeded through the S->N type of the Smiles rearrangement of the resulting 4,4'-dipyridinyl sulfide.In the case of formation of 10-(3'-nitro-4'-pyridinyl)-2,7-diazaphenothiazine (5)double rearrangement was observed.10H-2,7-diazaphenothiazine (4)was N-alkylated, N-arylated and N-heteroarylated to give 10-substituted (alkyl, arylalkyl, aryl, heteroaryl and dialkylaminoalkyl)derivatives (5)and (17-29).The NMR spectra were assigned with the help of the 1H-1H correlation (COSY)and NOE experiment of the methyl derivative (17).The crucial 10H-2,7-diazaphenothiazine (4)showed promising anticancer activity.