Alkylation of 4-oxo-3-methyl-4,5,6,7-tetrahydroindazoles |
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Authors: | I A Strakova E Yu Gudrinietse Ya Ya Linaberg A Ya Strakov D R Kreitsberga |
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Institution: | (1) Riga Polytechnic Institute, USSR |
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Abstract: | The alkylation of 4-oxo-3,6,6-trimethyl-4,5,6,7-tetrahydroindazole with alkyl halides forms mixtures of 1-alkyl and 2-alkyl derivatives which have been separated by fractional crystallization from n-hexane. The 4-oxo-1-alkyl-,-1-aryl-, and -1-acyl-4,5,6,7-tetrahydroindazoles have characteristic frequencies in their IR spectra at 1540-1530 cm–1, and the corresponding 2-substituted derivatives have frequencies at 1565-1555 cm–1. The introduction of an alkyl substituent at a nitrogen atom decreases the basicity of 4,5,6,7-tetrahydroindazole by 0.6 orders of magnitude, the 1-alkyl isomers being somewhat stronger bases than the 2-alkyl isomers. |
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