1,3-Dipolar cycloaddition of azomethine imines to ethynyl hetarenes: A synthetic route to 2,3-dihydropyrazolo[1,2-a]pyrazol-1(5H)-one based heterobiaryls

被引：7

作者：

Nelina-Nemtseva, Julia I. ^{[1
]}

Gulevskaya, Anna V. ^{[1
]}

Suslonov, Vitaliy V. ^{[2
,3
]}

Misharev, Alexander D. ^{[2
,3
]}

机构：

[1] Southern Fed Univ, Dept Organ Chem, Zorge 7, Rostov Na Donu 344090, Russia

[2] St Petersburg State Univ, Ctr Xray Diffract Studies, Univ Ski Pr 26, Peterhof 198504, Russia

[3] St Petersburg State Univ, Chem Anal & Mat Res Ctr, Univ Ski Pr 26, Peterhof 198504, Russia

来源：

TETRAHEDRON | 2018年 / 74卷 / 10期

关键词：

1,3-Dipolar cycloaddition; Azomethine imines; Ethynyl hetarenes; 6-Hetaryl-5-aryl-2,3-dihydropyrazolo[1,2-a]pyrazol-1(5H)-ones; Heterobiaryls; TERMINAL ALKYNES; BICYCLIC PYRAZOLIDINONES; BIOLOGICAL EVALUATION; DERIVATIVES; YLIDES; EFFICIENT; DESIGN; AGENTS; COMPLEXES; CHEMISTRY;

D O I：

10.1016/j.tet.2018.01.046

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

pi-Deficient ethynyl hetarenes were used as dipolarophiles in a 1,3-dipolar cycloaddition reaction with azomethine imines (2-arylidene-5-oxopyrazolidin-2-ium-1-ides). Both Cul-catalyzed and catalyst-free thermally induced reactions proceeded with high regioselectivity providing 6-hetaryl-5-aryl-2,3dihydropyrazolo[1,2-a]pyrazol-1(5H)-ones in moderate to excellent yields. The ethynyl hetarenes (pyridines, pyrazines, quinoxalines, pteridines and pyrimido[4,5-c]pyridazines) with ortho-methyl, orthocyano and ortho-alkynyl substituents were applicable to this reaction. 1,3-Dipolar cycloaddition reactions of alkynyl hetarenes with azomethine imines or other 1,3-dipole reagents can be considered as an alternative synthetic approach to heterobiaryls. (C) 2018 Elsevier Ltd. All rights reserved.

引用

页码：1101 / 1109

页数：9

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