Synthesis of the sulfonyl analog of hypoxanthine, imidazo [4,5-e]-1,2,4-thiadiazine 1,1-dioxide

Huang, Bao-Shan; Parham, James C.

doi:10.1021/jo01337a005

Cited by 10 publications

(1 citation statement)

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“…Various purine and pyrimidine analogs containing the sulfone moiety have been synthesized in the past (1)(2)(3)(4)(5) based on the rationale that this moiety can imitate the transition state that occurs during the enzymatic amination or deamination of their natural counterparts. Our interest in the preparation of potential inhibitors of cytidine deaminase led us to the synthesis of the title compound.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 4‐β‐D‐arabinofuranosyl‐5,6‐dihydro‐2H‐1,2,4‐thiadiazin‐3‐one 1,1‐dioxide and x‐ray diffraction analysis of its 2′,3‐anhydro precursor

Schroeder

Srikrishnan

Parthasarathy

et al. 1981

Journal of Heterocyclic Chem

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Reaction of 2-amino-3',5'-bis(0-tert-butyldimethylsilyl)-~-D-arabinofuran[l',2':4,5]-2-oxazoline with 2-chloroethylsulfonyl chloride in the presence of sodium bicarbonate followed by removal of the protecting groups gave 2',3-anhydro-4-~-D-arabinofuranosyl-5,6-dihydro-2H-1,2,4-thiadiazin-3-one 1,l-dioxide (5), which by treatment with ammonia was converted to 4-~-D-arabinofuranosyl-5,6-dihydro-2H-1,2,4-thiadiazin-%one 1,l-dioxide (6). The structure of compound 5 was unequivocally established by means of an x-ray diffraction analysis. The compound crystallized in the space group P2,2,2, with unit cell dimensions a = 5.883(3), b = 9.352(2), c = 18.769(7) A , Z = 4. Its structure was established by direct multisolution techniques and refined by the full matrix least squares method to a final R value of 0.058 for the 1515 reflections observed.

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Section: Introductionmentioning

confidence: 99%