New approach toward the synthesis of deuterated pyrazolo[1,5-a] pyridines and 1,2,4-triazolo[1,5-a] pyridines

被引：8
|
作者：
Vorob'ev, Aleksey Yu. [1 ,2 ]
Supranovich, Vyacheslav I. [1 ,2 ]
Borodkin, Gennady I. [1 ,2 ]
Shubin, Vyacheslav G. [1 ]
机构：
[1] Vorozhtsov Novosibirsk Inst Organ Chem, Acad Lavrentiev Ave 9, Novosibirsk 630090, Russia
[2] Novosibirsk State Univ, Pirogov St 2, Novosibirsk 630090, Russia
来源：
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 13卷
基金：
俄罗斯基础研究基金会;
关键词：
deuteration; 1,3-dipolar cycloaddition; pyrazolo[1,5-a]pyridine; 1,2,4-triazolo[1,5-a]pyridine; N-IMINOPYRIDINIUM YLIDES; DRUG DISCOVERY; INHIBITORS; DESIGN; POTENT; PHARMACOLOGY; DEUTERIUM; RECEPTOR; AGENTS;
D O I：
10.3762/bjoc.13.80
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient and operationally simple synthesis of 7-deuteropyrazolo[1,5-a] pyridine and 7-deutero-1,2,4-triazolo[1,5-a] pyridine derivatives using alpha-H/D exchange of 1-aminopyridinium cations in basic D2O followed by a 1,3-cycloaddition of acetylenes and nitriles is presented. A high regioselectivity and a high degree of deuterium incorporation were achieved. The procedure was applied for several 4-R-1-aminopyridinium cations (R = H, Me, OMe).
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页码：800 / 805
页数：6
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