A Synthesis of 2-Phenylimino-1,3-thiazoline Derivatives by Functionalization of α-D-glucopyranosyl Isothiocyanate
- A Synthesis of 2-Phenylimino-1,3-thiazoline Derivatives by Functionalization of α-D-glucopyranosyl Isothiocyanate
- 한호규; 마혜덕; 신동윤; 한민수; 남기달
- α-D-glucopyranose; phenylimino-1,3-thiazoline; glucosamine; isothiocyanate; thioureidothiazoline; phthalimide; chemistry library
- Issue Date
- Journal of Chitin and Chitosan; 한국키틴키토산학회지
- VOL 14, NO 1, 35-44
- As a part of fuctionalization of α-D-glucopyranosyl isothiocyanate 15, 2-(2-phenylimino-4-thioureido-1,3-thiazoline)-α-D-glucopyranose derivatives 16 were synthesized by the reaction of α-D-glucopyranosyl isothiocyanate 15 with 4-aminomethyl-1,3-thiazoline derivatives 6. An optimal reaction condition for a synthesis of α-D-glucosamine hydrogen chloride 12 was established by the reaction of D-glucosamine sequentially with diethylethoxymethylene malonate, acetic anhydride, and chlorine. α-D-glucopyranosyl isothiocyanate 15 was prepared from the dehydrochlorination of α-D-glucosamine hydrogen chloride 12 and then treated with thiophogene.
Bromination of 2-keto phthalimide which was obtained from the reaction of phthalimide potassium salts with chloroacetone gave 2-keto bromophthalimide 3 in high yield. This was reacted with an equal molar equivalent of N-methyl-N'-phenylthiourea derivatives 4, which were prepared independently to give the corresponding 4-phthalimidyl-1,3-thiazoline 5 in over 80% yield. 4-Aminomethyl-1,3-thiazoline intermediates 6 were synthesized by a deprotection of phthalimidyl moiety of 5 by the action of hydrazine, methylamine or ethanolamine, of which structures were confirmed by their 1H NMR spectra. Thus, the protons of amino methylene, 3-methyl and 5-vinyl showed in range of δ 1.3-1.8 ppm, 3.4-3.7 ppm and 5.7-5.8 ppm respectively without influence of functional group of the side chain. The characteristic doublet at 6.36 ppm with J1,2 3.3Hz in the 1H NMR of the target molecule α-anomer 16 confirmed the sterochemistry of the compound. The synthesized co
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