T. Afrough, M. Bakavoli, H. Eshghi
Jul 22, 2019
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Quality indicators
Journal
Polycyclic Aromatic Compounds
Abstract
Abstract A new methodology for the synthesis of 4-(1-(pyrimidin-4-yl)ethyl)-12H-pyrimido[4′,5′:5,6][1,4]thiazino[2,3-b]quinoxaline derivatives 5a-g was introduced. Condensation of 5-bromo-4-[1-(5-bromo-2,6-dichloropyrimidin-4-yl)ethyl]-2-chloro-6-methylpyrimidine 2 and 3-aminoquinoxaline-2-thiol 3 gave either regioisomers 4 or 4′. The computational and spectral data of both regioisomers confirmed the occurrence of the S/N type Smiles rearrangement during the course of the reaction. Treatment of the foregoing compound with various secondary amines gave several new 4-(1-(pyrimidin-4-yl)ethyl)-12H-pyrimido[4′,5′:5,6][1,4]thiazino[2,3-b]quinoxaline derivatives 5a-g. The newly synthesized compounds were evaluated for their potential antibacterial activity and the results exhibit two of the derivatives are moderately valuable compounds in comparison with three reference drugs.