HETEROCYCLIZATION OF 3-(R-AMINO)-3-METHYLTHIO-1-PHENYLPROPENONES AND 5-BENZOYL-6-METHYLTHIO-1,2-DIHYDROPYRIDIN-2-ONES WITH 1,2- AND 1,3-DINUCLEOPHILIC REAGENTS
DOI:
https://doi.org/10.1007/1413Keywords:
1-alkyl-5-benzoyl-3-ethoxycarbonyl-6-methylthio-1, 2-dihydropyridin-2-ones, 6-amino-5-benzoyl-3-ethoxycarbonyl-1-methyl-1, 2-dihydropyridin-2-one, 3-(R-amino)-3-methylthio-1-phenyl-propenones, 1-R1-5-(R-amino)-3-phenylpyrazoles, benzimidazo[1, 2-a]pyridines, 2-a]pyrimidines, 6, 7-dihydro-2H-pyrazolo[3, 4-b]pyridines, 1, 2, 4-triazole, [1, 4]triazolo[4, 3-b]pyridazines, heterocyclization, [3 2] cyclocondensation, [3 3] cyclocondensationAbstract
The interaction of 3-(R-amino)-3-methylthio-1-phenylpropenones and 1-alkyl-5-benzoyl-3-ethoxy-carbonyl-6-methylthio-1,2-dihydropyridin-2-ones with N,N- and N,C-1,2- and 1,3-dinucleophiles proceeded regioselectively by [3+2] and [3+3] cyclocondensation with the formation of derivatives of pyrazole, benzimidazo[1,2-a]-pyridine, benzimidazo[1,2-a]pyrimidine, imidazo[1,2-a]pyrimidine, [1,2,4]triazolo[4,3-b]pyridazine, and 6,7-dihydro-2H-pyrazolo[3,4-b]pyridine. The regioselectivity of the reactions carried out was analyzed.
Authors: V. N. Britsun, N. V. Pikun, A. B. Ryabitskii, and M. O. Lozinskii.
English translation in Chemistry of Heterocyclic Compounds, 2011, 47 (8), pp 970-976
