Synthesis of Some Mono-, Bis- NH-substituted-1,4-Benzoquinones

The preparation of new mono- and bis- NH-substituted-1,4-benzoquinones, namely 2,5-bis(5,6-dimethylbenzo[d]thiazol-2-ylamino)cyclohexa-2,5-diene-1,4-dione ( 3 ), 2,5-bis(3-(2-methylpiperidin-1-yl)propylamino)-3-chlorocyclohexa-2,5-diene-1,4-dione ( 6 ), 2-(4-tert-butylbenzylamino)-3,5,6-trichlorocyclohexa-2,5-diene-1,4-dione ( 9 ), 2-(4-fluorophenylamino)-6-tert-butylcyclohexa-2,5-diene-1,4-dione ( 12 ) is reported. The synthesis of new quinone derivatives ( 3 , 6 , 9 , 12 ) have been carried out from the reactions between quinones ( p -benzoquinone ( 1 ), 2,6-dichloro-1,4-benzoquinone ( 4 ), tetrachloro-1,4-benzoquinone ( 7 ), 2-tert-butyl-1,4-benzoquinone ( 10 )) and different amines (2-Amino-5,6-dimethylbenzothiazole ( 2 ), N-(3-aminopropyl)-2-pipecoline ( 5 ), 4-tert-butylbenzylamine ( 8 ), 4-fluoroaniline ( 11 )). The new compounds were characterized by elemental analysis, mass spectrometry, IR, 1 H-NMR, 13 C-NMR spectroscopy.