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

页码：1563 / 1568

页数：6

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