The reaction of 3-carboxy-1, 2-dihydro-1-methyl-2-oxopyridine (V) with diazomethane afforded 6, 7-dihydro-1, 6-dimethyl-7-oxopyrazolo [3, 4-c] pyridine (VI), 4, 5, 6, 7-tetrahydro-1, 6-dimethyl-7-oxopyrazolo [3, 4-c] pyridine (VII), and 1, 2-dihydro-3-methoxycarbonyl-1, 4-dimethyl-2-oxopyridine (VIII). 1-Ethyl-6, 7-dihydro-3, 6-dimethyl-7-oxopyrazolo [3, 4-c] pyridine (XXI), 8a-ethoxycarbonyl-1, 4, 4a, 7, 8, 8a-hexahydro-3, 4, 7-trimethyl-8-oxopyrido [3, 4-c] pyridazine (XXII), and 3-ethoxycarbonyl-4-ethyl-1, 2-dihydro-1-methyl-2-oxopyridine (XXIII) were obtained from the reaction of compound (V) with diazoethane. The treatment of 4-carboxy-1, 2-dihydro-1-methyl-2-oxopyridine (XXVIII) with diazomethane gave 1, 2-dihydro-4-methoxycarbonyl-1-methyl-2-oxopyridine (XXIX), 6-methoxycarbonyl-3-methyl-2-oxo-3-azabicyclo [4. 1. 0] hept-4-ene (XXX), and 1, 2-dihydro-4-methoxycarbonyl-1, 3-dimethyl-2-oxopyridine (XXXI). The reaction of compound (XXIX) with diazoethane afforded 3-ethyl-1, 2-dihydro-4-methoxycarbonyl-1-methyl-2-oxopyridine (XXXII), 6α-methoxycarbonyl-3, 7β-dimethyl-2-oxo-3-azabicyclo [4, 1, 0]-hept-4-ene (XXXIII), and 1-ethyl-6-methoxycarbonyl-3, 7-dimethyl-2-oxo-3-azabicyclo [4. 1. 0] hept-4-ene (XXXIV). In case of the treatment of 5-carboxy-1, 2-dihydro-1-methyl-2-oxopyridine (XXXV) and 1, 5-dihydro-1, 5-dioxo-3H-oxazolo [3, 4-a] pyridine (XXXVIII) with diazomethane, 1, 2-dihydro-5-methoxycarbonyl-1-methyl-2-oxopyridine (XXXVI) and 1, 2-dihydro-6-methoxycarbonyl-1-methyl-2-oxopyridine (XXXIX) were obtained, respectively.
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