通过[4 + 2]环加成反应合成嘧啶核苷类似物的有效途径。

An efficient route to pyrimidine nucleoside analogues by [4 + 2] cycloaddition reaction.

作者信息

Pearson Morwenna S M, Robin Aélig, Bourgougnon Nathalie, Meslin Jean Claude, Deniaud David

机构信息

Laboratoire de Synthèse Organique, UMR CNRS 6513, Faculté des Sciences et des Techniques, 2, Rue de la Houssinière 44322 Nantes 03, France.

出版信息

J Org Chem. 2003 Oct 31;68(22):8583-7. doi: 10.1021/jo034709a.

DOI:10.1021/jo034709a

PMID:14575489

Abstract

We report here an efficient synthesis for pyrimidine nucleoside analogues by [4 + 2] cycloaddition reaction. These compounds were obtained by convergent chemistry from glycosyl isothiocyanates 3a-f (pyranoses, furanoses, and dissaccharides) and diazadienium salt 5. In fact, diazapentadienium iodide 5 prepared from vinylthioamide 4 is an efficient intermediate in heterocyclic synthesis and reacts with isothiocyanates 3a-f affording beta-D-uracil analogues 7a-f in good yields and with total regiocontrol. All compounds were fully characterized by IR, HRMS, and 13C and 1H NMR (COSY and HMQC).

摘要

我们在此报道了一种通过[4 + 2]环加成反应高效合成嘧啶核苷类似物的方法。这些化合物是通过收敛化学法由糖基异硫氰酸酯3a - f（吡喃糖、呋喃糖和二糖）与重氮二烯盐5制得的。事实上，由乙烯硫酰胺4制备的碘化重氮戊二烯5是杂环合成中的一种有效中间体，它与异硫氰酸酯3a - f反应，以良好的产率和完全的区域选择性得到β - D - 尿嘧啶类似物7a - f。所有化合物均通过红外光谱（IR）、高分辨质谱（HRMS）以及碳-13（13C）和氢-1（1H）核磁共振（COSY和HMQC）进行了全面表征。