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Publikācija: Reactions of Cyclic Lactim Methylesters with Hydrazides of Cyclohexenedicarboxylic Acids

Publication Type Publications in RTU scientific journal
Funding for basic activity Unknown
Defending: ,
Publication language Latvian (lv)
Title in original language Ciklisko laktīmu metilēteru reakcijas ar cikloheksēndikarbonskābes hidrazīdiem
Title in English Reactions of Cyclic Lactim Methylesters with Hydrazides of Cyclohexenedicarboxylic Acids
Field of research 1. Natural sciences
Sub-field of research 1.4 Chemical sciences
Authors Irisa Rāviņa
Zenta Tetere
Daina Zicāne
Keywords lactams, cyclohexenedicarboxylic acid, hydrazides, triazoles, diazaspiroderivatives, amidrazones
Abstract Viena no ciklisko laktīmu metilesteru sintēzes metodēm ir attiecīgo laktāmu reakcijas ar dimetilsulfātu. Iegūtie savienojumi reaģē ar acilhidrazīniem, tajā skaitā karbonskābju hidrazīdiem. Minētajās reakcijās veidojas lineāri savienojumi, kuri, izšķeļot ūdeni, ciklizējas. Šajā darbā pētītas cikloheksēndikarbonskābju reakcijas ar tri-, tetra- un pentametilēnlaktīmēteriem. Pirmajā reakcijas stadijā veidojas abu komponentu kondensācijas savienojumi − ,,amidrazoni”, otrajā to ciklizācijas produkti. Atkarībā no ,,amizadronu” struktūras rodas triazoli, kas C(4) un C(5) vietās saistīti ar metilēnsavienojumu ciklu, vai attiecīgie diazaspiroatvasinājumi.
Abstract in English 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.
Reference 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.
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