Abstract
[3+3] Cyclocondensation of 5-benzoyl-3-ethoxycarbonyl-6-methylthio-1-R-1,2-dihydropyrid-2-ones with heterocyclic N,N-and N,C-1,3-dinucleophiles proceeds regioselectively to give a series of new tri-and tetracyclic heterosystems, viz. derivatives of 5,6-dihydropyrazolo[1,5-a]pyrido[2,3-d]pyrimidin-6-one, 1,2-dihydropyrido[2,3-d]pyrido[2′,3′: 3,4]pyrazolo[1,5-a]pyrimidin-2-one, 8,9-dihydro-5H-pyrido-[2,3-d]thiazolo[3,2-a]pyrimidin-8-one, 1,2-dihydrobenzo[4,5]imidazo[1,2-a]pyrido[2,3-d]pyrimidin-2-one, and 1,2-dihydrobenzo[4,5]imidazo[1,2-g][1,6]naphthyridin-2-one.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1216–1222, August, 2008.
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Britsun, V.N., Esipenko, A.N., Piroghenko, V.V. et al. Cyclocondensation of 5-benzoyl-3-ethoxycarbonyl-6-methylthio-1-R-1,2-dihydropyrid-2-ones with heterocyclic N,N-and N,C-1,3-dinucleophiles. Chem Heterocycl Comp 44, 979–984 (2008). https://doi.org/10.1007/s10593-008-0142-1
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DOI: https://doi.org/10.1007/s10593-008-0142-1
Keywords
- 2-aminobenzimidazole
- 3-amino-2H-pyrazolo[3,4-b]pyridine
- 5-amino-3-R1-4-R2-pyrazoles
- 2-amino-5-R-thiazoles
- 5-benzoyl-3-ethoxycarbonyl-6-methylthio-1-R-1,2-dihydropyridin-2-ones
- 7-ethoxycarbonyl-5-hydroxy-9-methyl-5-phenyl-2-R-8,9-dihydro-5H-pyrido[2,3-d]thiazolo[3,2-a]pyrimidin-8-ones
- 3-ethoxycarbonyl-5-phenyl-1-R-1,2-dihydrobenzo[4,5]imidazo[1,2-a]pyrido[2,3-d]pyrimidin-2-ones
- 7-ethoxycarbonyl-9-phenyl-5-R1-3-R2-2-R3-5,6-dihydropyrazolo[1,5-a]pyrido[2,3-d]pyrimidin-6-ones
- 3-ethoxycarbonyl-5-phenyl-1-R-1,2-dihydropyrido[2,3-d]pyrido[2′,3′:3,4]pyrazolo[1,5-a]pyrimidin-2-ones
- 12-cyano-3-ethoxycarbonyl-5-phenyl-1-R-1,2-dihydrobenzo[4,5]imidazo[1,2-g][1,6]naphthyridin-2-ones
- 2-(cyanomethyl)benzimidazole
- heterocyclization
- [3+3] cyclocondensation