Synthesis of nitrogen-15-labeled 2-amino(glycofurano)oxazolines via glycosylamine intermediates
作者:Robert M. Davidson、Edward White、Sam A. Margolis、Bruce Coxon
DOI:10.1016/0008-6215(83)88113-0
日期:1983.6
Abstract A new, efficient synthesis of doubly 15N-labeled 2-amino-oxazoline derivatives of pentoses and hexoses has been delineated that involves treatment either of unprotected or O-isopropylidenated glycosylamines with cyanamide-15N2 in methanol to give 2-amino(glycofurano)oxazolines-15N2. A probable mechanism for these reactions is presented. These techniques provide a practical means by which a
Azoles as Auxiliaries and Intermediates in Prebiotic Nucleoside Synthesis
作者:Dougal J. Ritson、Mikolaj W. Poplawski、Andrew D. Bond、John D. Sutherland
DOI:10.1021/jacs.2c07774
日期:2022.10.26
ribo-aminooxazoline in formamide to give ribo-anhydrocytidine ─ an intermediate in the divergent synthesis of purine and pyrimidine nucleotides. We also report a prebiotically plausible synthesis of 2-aminothiazole and examine the mechanism of its formation. The utilization of each of these azoles enhances the prebiotic synthesis of ribonucleotides, while their syntheses comport with the cyanosulfidic scenario we
4,5-二氰基咪唑和 2-氨基噻唑是以前与益生元核苷酸合成有关的唑类。前一种化合物是腺嘌呤合成的副产物,而后一种化合物已被证明能够通过结晶分离 C 2和 C 3糖作为它们的缩醛胺。我们现在报告说,难以捉摸的中间体氰基乙炔可以被 4,5-二氰基咪唑捕获并积累为结晶化合物N-氰基乙烯基-4,5-二氰基咪唑,从而解决大气中形成的氰基乙炔的浓度问题。重要的是,该中间体是一种有效的氰基乙炔替代物,在甲酰胺中与核糖氨基恶唑啉反应生成核糖-脱水胞苷 ─ 嘌呤和嘧啶核苷酸不同合成的中间体。我们还报告了 2-氨基噻唑的益生元合成,并研究了其形成机制。这些唑类中的每一种的利用都增强了核糖核苷酸的益生元合成,而它们的合成与我们之前描述的氰基硫化物情景相一致。
Huenig, Siegfried; Bau, Robert; Kemmer, Martina, European Journal of Organic Chemistry, 1998, # 2, p. 335 - 348