2-N-置換-cephemの合成研究(第2報)2-CephemとIN_3との反応について
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概要
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Reaction of p-methoxybenzyl 7β-phenylacetamido-3-methyl-2-cephem-4α-carboxylate (1) with NaN_3 and ICl were carried out. In CH_3CN or AcOEt, two iodoazides (2a, 2b), in CH_3NO_2 or CCl_4,the diazide (3) and in dioxane or CH_2Cl_2,the chloroazide (4) were obtained. Treatment of 2a, 2b and 4 with DABCO gave 2-azido-3-cephem. The same treatment of 3 gave 2-azido-2-cephem. By replacement of 7β-amido group or ester group, the same results were obtained. As a simple model of olefins, reaction of benzo [b] thiophene with NaN_3 and ICl gave diazide, from which HN_3 was eliminated by tert-BuOK. Configuration of 2-azidocephams and cephems were discussed.
- 公益社団法人日本薬学会の論文
- 1982-09-25
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