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Reactions of 5-Mercapto-3-(4′-pyridyl)-s-triazole with alpha-Halogenoketones, 1,2-Dibromoethane and 2,3-Dichloroquinoxaline: Synthesis of Thiazolo<2,3-c>-s-triazoles and s-Triazolo<3',4':2,3>thiazolo<4,5-b>quinoxaline
5-Mercapto-3-(4′-pyridyl)-s-triazole (I; R = 4-pyridyl) reacts with alpha-halogenoketones to give 5-aroylmethylthio-3-(4′-pyridyl)-s-triazoles (IIa-f) which on treatment with PPA undergo cyclodehydration to furnish 5-aryl-3-(4′-pyridyl)thiazolo<2,3-c>-s-triazoles (IIIa-f) and not the isomeric 5-aryl-2-(4′-pyridyl)thiazolo<3,2-b>-s-triazoles (VIIIa-f).The structural assignments of III are based on elemental analyses, spectral data and the unequivocal synthesis of IIIa (R = 4-pyridyl; R1 = p-ClC6H4) by POCl3 cyclization of 4-(p-chlorophenyl)-2-isonicotinylhydrazinothiazole (V) obtained from isonicotinyl thiosemicarbazide (IV) and p-chlorophenacyl bromide.A similar condensation of I (R = 4-pyridyl) with 1,2-dibromoethane yields 5,6-dihydro-3-(4′-pyridyl)thiazolo<2,3-c>-s-triazole (VI) and not its isomer, 5,6-dihydro-2-(4′-pyridyl)thiazolo<3,2-b>-s-triazole (IX).This has also been proved by the unequivocal synthesis of VI by the reaction of IV with 1,2-dibromoethane.The reaction of I (R = 4-pyridyl) with 2,3-dichloroquinoxaline gives 3-(4′-pyridyl)-s-triazolo<3',4':2,3>thiazolo<4,5-b>quinoxaline (VII).
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Reference£º
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N1376 | ChemSpider