Synthesis of ([1,2,4]triazolo[4,3-a]pyridin-3-ylmethyl)phos-phonates and their benzo derivatives via 5-exo-dig cyclization

被引：11
作者：
Krylov, Aleksandr S. [1 ]
Petrosian, Artem A. [1 ]
Piterskaya, Julia L. [1 ]
Svintsitskaya, Nataly, I [1 ]
Dogadina, Albina, V [1 ]
机构：
[1] St Petersburg State Inst Technol, Dept Organ Chem, St Petersburg 190013, Russia
来源：
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 15卷
基金：
俄罗斯基础研究基金会;
关键词：
cyclization; fused-ring systems; nitrogen heterocycles; phosphorylation; rearrangement; ONE-POT SYNTHESIS;
D O I：
10.3762/bjoc.15.159
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A series of novel 3-methylphosphonylated [1,2,4]triazolo[4,3-a]pyridines was accessed through a 5-exo-dig-type cyclization of chloroethynylphosphonates and commercially available N-unsubstituted 2-hydrazinylpyridines. In addition, 3-methylphosphonylated [1,2,4]triazolo[4,3-a]quinolines and 1-methylphosphonylated [1,2,4]triazolo[3,4-a]isoquinolines were synthesized in a similar manner. The presence of a NO2 group in the starting hydrazinylpyridine induces a Dimroth-type rearrangement leading to 2-methylphosphonylated [1,2,4]triazolo[1,5-a]pyridines.
引用
收藏
页码：1563 / 1568
页数：6
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