Design of hybrid heterocyclic systems with a furoxanylpyridine core via tandem hetero-Diels-Alder/retro-Diels-Alder reactions of (1,2,4-triazin-3-yl)furoxans

被引：45

作者：

Fershtat, Leonid L. ^{[1
]}

Larin, Alexander A. ^{[1
]}

Epishina, Margarita A. ^{[1
]}

Ovchinnikov, Igor V. ^{[1
]}

Kulikov, Alexander S. ^{[1
]}

Ananyev, Ivan V. ^{[2
]}

Makhova, Nina N. ^{[1
]}

机构：

[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, 47 Leninsky Prosp, Moscow 119991, Russia

[2] Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, 28 Vavilova Str, Moscow 119991, Russia

来源：

RSC ADVANCES | 2016年 / 6卷 / 37期

基金：

俄罗斯科学基金会;

关键词：

NUCLEOPHILIC-SUBSTITUTION; MEDIATED SYNTHESIS; EFFICIENT ROUTE; 2,2'-BIPYRIDINE; AZADIENES; 1,2,4-TRIAZINES; BENZOFUROXANS; CYCLOADDITION; FUROXAN; ACCESS;

D O I：

10.1039/c6ra05110c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Two convenient, facile, regioselective and highly effective one-pot protocols for the synthesis of previously unknown hybrid heterocyclic systems with the furoxanylpyridine core based on the tandem inverse-electron-demand hetero-Diels-Alder/retro-Diels-Alder reactions of the tailor-made (1,2,4-triazin-3-yl)furoxans with 1-(pyrrolidino)cyclohexene and norbornadiene have been developed. The methods comprise [4 + 2] cycloaddition of enamine or norbornadiene to the 1,2,4-triazine ring of (1,2,4-triazin-3-yl)furoxans followed by one-pot transformation of the formed intermediates and this affords an extensive series of polyheterocyclic ensembles combining furoxan and pyridine (tetrahydroisoquinoline, indenopyridine, terpyridine) rings in one molecule through a C-C bond in good to excellent yields.

引用

页码：31526 / 31539

页数：14

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