ChemInform Abstract: Alkylation of Xanthine and Benzimidazole Derivatives with Epithiochlorohydrine.

Abstract

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New synthesis of 6,7-dihydro[1,3]thiazolo[2,3-f]purine-2,4(1H,3H)-diones

“…The properties of compound IIIa were consistent with published data [1]. Substituted thiiranes IIb and IIc gave rise to 7-substituted dihydrothiazolopurines IIIb and IIIc whose structure was additionally proved by independent synthesis of compound IIIb from 8-bromo-1,3-dimethyl-7-(thiiran-2-ylmethyl)-3,7-dihydro-1H-purine-2,6-dione and diethylamine [2]. Samples of IIIb prepared by the two methods showed no depression of the melting point on mixing, and their 1 H NMR spectra were fully identical.…”

“…Several methods of synthesis of 6,7-dihydro [1,3]thiazolo[2,3-f]purine-2,4(1H,3H)-diones have been reported, e.g., from 8-brom-7-(2-haloethyl)-3,7-dihydro-1H-purine-2,6-diones and sodium sulfide [1], by reaction of 8-halo-7-(thiiran-2-ylmethyl)-3,7-dihydro-1H-purin-2,6-diones with nucleophilic reagents [2], etc. We now propose a new one-step procedure for the preparation of 6,7-dihydro [1,3]thiazolo[2,3-f]purin-2,4(1H,3H)-dione derivatives via reaction of 8-halo-3,7-dihydro-1H-purine-2,6-diones with thiiranes.…”

Reactions of 1,2,4-triazole derivatives with a “model” thiirane

“…1 H NMR spectrum of compound III confirmed the formation of the fused system of the dihydrothiazolopurine: characteristic multiplets appeared in the regions 4.62-4.74 and 4.96-5.06 ppm, corresponding to the protons of NCH 2 and SCH groups of the dihydrothiazole ring respectively [5,6].…”

Thietanyl protection in the synthesis of 1-alkyl-8-bromo-3-methyl-3,7-dihydro-1H-purine-2,6-diones

“…The 8-bromo-3-methyl-7-(thietan-3-yl)-3,7-dihydro-1H-pyrine-2,6-dione (I) formed as a result of the thiirane-thietane rearrangement [5] (Scheme 1).…”