Synthesis of electron-poor 4-halo-2-azabuta-1,3-dienes by Rh(II)-catalyzed diazo ester-azirine coupling. 2-Azabuta-1,3-diene-2,3-dihydroazete valence isomerism

被引：18

作者：

Novikov, Mikhail S. ^{[1
]}

Smetanin, Ilia A. ^{[1
]}

Khlebnikov, Alexander F. ^{[1
]}

Rostovskii, Nikolai V. ^{[1
]}

Yufit, Dmitry S. ^{[2
]}

机构：

[1] St Petersburg State Univ, Dept Chem, St Petersburg 198504, Russia

[2] Univ Durham, Dept Chem, Durham DH1 3LE, England

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 43期

基金：

俄罗斯基础研究基金会;

关键词：

Azirines; Diazo compounds; Carbenoids; Ylides; 2-Azabuta-1,3-dienes; 2,3-Dihydroazetes; Electrocyclic reactions; CYCLOADDITION; 2H-AZIRINES; CHEMISTRY;

D O I：

10.1016/j.tetlet.2012.08.063

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Rh-2(OAc)(4)-catalyzed reaction of alkyl 2-acyl-2-diazoacetates and dimethyl diazomalonate with methyl 2-bromo- and 2-chloro-3-phenyl-2H-azirine-2-carboxylates gives rise to electron-poor 4-halo-substituted (3E)-2-azabuta-1,3-dienes. Their formation proceeds with complete stereoselectivity via ring-opening of the intermediate azirinium ylide. 2-Azabuta-1,3-dienes with electron-withdrawing substituents at the 1,1,4-positions are stable compounds at room temperature, but are in equilibrium with cyclic valence isomers, 2,3-dihydroazetes, at elevated temperatures. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：5777 / 5780

页数：4

共 3 条

[1] 4-Halo-2-azabuta-1,3-dienes as intermediates in the rhodium carbenoid-initiated transformation of 2-halo-2H-azirines into 2,3-dihydroazetes and 2,5-dihydrooxazoles
Smetanin, Ilia A.
Novikov, Mikhail S.
Rostovskii, Nikolai V.
Khlebnikov, Alexander F.
Starova, Galina L.
Yufit, Dmitry S.
TETRAHEDRON, 2015, 71 (28) : 4616 - 4628
[2] Pseudopericyclic 1,5- versus Pericyclic 1,4- and 1,6-Electrocyclization in Electron-Poor 4-Aryl-2-azabuta-1,3-dienes: Indole Synthesis from 2H-Azirines and Diazo Compounds
Novikov, Mikhail S.
Khlebnikov, Alexander F.
Rostovskii, Nikolai V.
Tcyrulnikov, Sergei
Suhanova, Anna A.
Zavyalov, Kirill V.
Yufit, Dmitry S.
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (01): : 18 - 29
[3] Pseudopericyclic Dearomative 1,6-Cyclization of 1-(2-Pyridyl)-2-azabuta-1,3-dienes: Synthesis and Ring-Chain Valence Equilibria of 4H-Pyrido[1,2-a]pyrazines
Filippov, Ilya P.
Novikov, Mikhail S.
Khlebnikov, Alexander F.
Rostovskii, Nikolai V.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (19) : 2904 - 2913

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