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.
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*Deceased. (M. O. Lozinskii)
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1183–1190, August, 2011.
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Britsun, V.N., Pikun, N.V., Ryabitskii, A.B. et al. 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. Chem Heterocycl Comp 47, 970–976 (2011). https://doi.org/10.1007/s10593-011-0862-5
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DOI: https://doi.org/10.1007/s10593-011-0862-5
Keywords
- 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
- benzimidazo[1,2-a]-pyrimidines
- 6,7-dihydro-2H-pyrazolo[3,4-b]pyridines
- 1,2,4-triazole
- [1,2,4]triazolo[4,3-b]pyridazines
- heterocyclization
- [3 + 2] and [3 + 3] cyclocondensations