Reactions of Cyclic Lactim Methylesters with Hydrazides of Cyclohexenedicarboxylic Acids
2011
Irisa Rāviņa, Zenta Tetere, Daina Zicāne

The cyclic lactim methylesters, prepared by the reaction of lactams with dimethylsulphate, react with nucleophylic compounds. Aiming at acquiring new products possessing biological activity we realised reactions of 1-hydroxycarbonyl-2-(4-R-phenyl)-4-methyl-4-cyclohexenylhydr-azides with tri-, tetra- and pentamethylene lactim ethers. These reactions often proceed in two stages. Lactim methylethers with hydrazides of cyclohexenedicarboxylic acids form hydrazidoazacycloalkenes. Very low solubility of these compounds made their NMR spectroscopy impossible. Only in two cases the NMR spectral analyses was successful. 2-[2-(4-R)-Phenyl-1-hydroxycarbonyl-4-methylcyclohexenylhydrazido-1-azacycloalkenes reacted with acetic acid to cyclize. In the case of trimethylene azacyclohydrazides diazaspiroderivatives were obtained. Similar reactions with tetramethylene- and pentamethylene azacyclohydrazides gave triazole derivatives. The structure of the products was determined by NMR and IR spectroscopies and confirmed with elemental analyses. Cyclization of trimethylene azacyclohydrazides yielded two diastereoisomers in ratio 2:1 or 1,2:1 (C=H), while tetra- and pentamethylene derivatives gave only one diastereoisomer.


Keywords
lactams, cyclohexenedicarboxylic acid, hydrazides, triazoles, diazaspiroderivatives, amidrazones

Rāviņa, I., Tetere, Z., Zicāne, D. Reactions of Cyclic Lactim Methylesters with Hydrazides of Cyclohexenedicarboxylic Acids. Materials Sciences and Applied Chemistry. Vol.23, 2011, pp.9-12. ISSN 1407-7353.

Publication language
Latvian (lv)
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