由酰肼氯化物和腈类化合物合成1,2,4-三唑C-核苷。

Synthesis of 1,2,4-triazole C-nucleosides from hydrazonyl chlorides and nitriles.

作者信息

Al-Masoudi Najim A, Al-Soud Yaseen A, Ali Ibrahim A I

机构信息

Formerly Fachbereich Chemie, Universität Konstanz, Konstanz, Germany.

出版信息

Nucleosides Nucleotides Nucleic Acids. 2007;26(1):37-43. doi: 10.1080/15257770601052265.

DOI:10.1080/15257770601052265

PMID:17162585

Abstract

A series of 1,3-diaryl-5-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-1H-1,2,4-triazole nucleosides (3a-f) were synthesized via the intermolecular cyclization of hydrazonyl chlorides with peracylated ribofuranosyl cyanide catalyzed by Yb(OTf)3 or AgNO3, respectively. Similarly, the 1,2,4-triazole of glucopyranosyl C-nucleosides 5a,b were prepared from the hydrazonyl chlorides and the nitrile 4. Alternatively, the 1,2,4-triazole N-nucleoside 8 was obtained from cyclization of the unsymmetrical bis[alpha-(4-methoxyphenyl)aminobenzylidene]-hydrazine with peracylated 1-amino-D-manno-pentitol.

摘要

通过分别由Yb(OTf)3或AgNO3催化的酰肼氯化物与全酰化呋喃核糖基氰化物的分子内环化反应，合成了一系列1,3 - 二芳基 - 5 - (2,3,5 - 三 - O - 苯甲酰基 - β - D - 呋喃核糖基) - 1H - 1,2,4 - 三唑核苷(3a - f)。同样地，吡喃葡萄糖基C - 核苷5a,b的1,2,4 - 三唑是由酰肼氯化物和腈4制备的。另外，不对称双[α - (4 - 甲氧基苯基)氨基亚苄基]肼与全酰化1 - 氨基 - D - 甘露戊糖醇环化反应得到1,2,4 - 三唑N - 核苷8。