Metal-Catalyzed Isomerization of 5-Heteroatom-Substituted Isoxazoles as a New Route to 2-Halo-2 H -azirines

被引：30

作者：

Rostovskii, Nikolai V. ^{[1
]}

Agafonova, Anastasiya V. ^{[1
]}

Smetanin, Ilia A. ^{[1
]}

Novikov, Mikhail S. ^{[1
]}

Khlebnikov, Alexander F. ^{[1
]}

Ruvinskaya, Julia O. ^{[1
]}

Starova, Galina L. ^{[1
]}

机构：

[1] St Petersburg State Univ, Inst Chem, 7-9 Univ Skaya Nab, St Petersburg 199034, Russia

来源：

SYNTHESIS-STUTTGART | 2017年 / 49卷 / 19期

基金：

俄罗斯科学基金会;

关键词：

azirines; isoxazoles; haloheterocycles; rhodium(II) carboxylates; iron(II) chloride; catalysis; isomerization; RING EXPANSION; FACILE SYNTHESIS; 2H-AZIRINES; REACTIVITY; 2-HALO-2H-AZIRINES; PYRIDINES; 4-HALO-2-AZABUTA-1,3-DIENES; CYCLOADDITIONS; TRANSFORMATION; REARRANGEMENT;

D O I：

10.1055/s-0036-1590822

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient gram-scale method for the preparation of 2-halo-2H-azirine-2-carboxylic acid esters, thioesters and amides via metal-catalyzed isomerization of 5-heteroatom-substituted 4-haloisoxazoles is developed. The formation of the esters and amides is efficiently catalyzed by Rh-2(Piv)(4), while FeCl(2)4H(2)O is the catalyst of choice for the synthesis of the thioesters. In addition, rhodium catalysis is successfully applied in the synthesis of azirine-2-carboxylates from non-halogenated 5-alkoxyisoxazoles.

引用

页码：4478 / 4488

页数：11

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