Obtaining New Biologically Active Compounds from 2-Vinyloxyethylisothiocyanate
O. A. NURKENOV,В В I. V. KULAKOV,В В S. D. FAZYLOV andВ В A. ZH. SARSENBEKOVA
Institute of Organic Synthesis and Coal Chemistry, NAS of Kazakhstan, Ul. Alikhanova 1, Karaganda 100008 (Kazakhstan),
E-mail: kulakov_iv@mail.ru
Keywords: vinyloxyethylisothiocyanate, alkaloids, cytisine, anabasine, l-ephedrine, d-pseudoephedrine, XRD structural analysis
Pages: 537–545
Abstract
Via the reaction of alkaloid cytisine, l-ephedrine, d-pseudoephedrine as well as glucosylbenzylamine and xylosylbenzylamine aminoglycosides with vinyloxyethylisothiocyanate and its acetal derivatives, we synthesized and characterized novel 2-vinyl-, N-1-propargyl-, 1-N-phenyloxyethoxyethylo-N’-aminothiourea species. By the example of the N-vinylethoxythiocarbamoyl derivatives of l-ephedrine and d-pseudoephedrine is demonstrated that the mentioned thiourea species could quite readily undergo hydrolyzing in the presence of acids. On the basis of salicylic acid hydrazide we have synthesized and studied the acidic hydrolysis of corresponding vinyloxyethylthiosemicarbazide. The composition and the structure of the thiourea derivatives synthesized were confirmed by IR spectroscopy, 1H NMR, 13C NMR and mass spectrometry as well as by XRD structural analysis.
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