Synthesis of 2-halo-2De-azirine-2-carboxylic acid amides and esters by isomerization of 5-(dialkylamino/alkoxy)-substituted isoxazoles, catalyzed by iron(II) sulfate

被引：19

作者：

Agafonova, Anastasiya V. ^{[1
]}

Smetanin, Ilia A. ^{[1
]}

Rostovskii, Nikolai V. ^{[1
]}

Khlebnikov, Alexander F. ^{[1
]}

Novikov, Mikhail S. ^{[1
]}

机构：

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

来源：

CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2017年 / 53卷 / 10期

基金：

俄罗斯科学基金会;

关键词：

2H-azirines; halogenated heterocycles; iron(II) salts; isoxazoles; catalysis; rearrangements; RELAY CATALYSIS; TRANSFORMATION; CYCLOADDITION; 2H-AZIRINES; ANNULATION; OXAZOLES; CLEAVAGE; ACCESS;

D O I：

10.1007/s10593-017-2172-z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N,N-Dialkylamides and esters of 2-(chloro/bromo/iodo)-2H-azirine-2-carboxylic acids were synthesized by isomerization of 4-halo-5-(dialkylamino/alkoxy)isoxazoles in the presence of catalytic amounts of FeSO4 center dot 7H(2)O. The use of iron(II) sulfate as catalyst, compared to its chloride, provides the advantage of avoiding halide exchange products in isomerization reactions of 4-bromo- and 4-iodoisoxazoles, as well as prevents catalyst deactivation by the 5-amino substituent of isoxazole, compared to rhodium(II) carboxylates.

引用

页码：1068 / 1071

页数：4

共 26 条

[11] Domino transformation of isoxazoles to 2,4-dicarbonylpyrroles under Fe/Ni relay catalysis [J].

Galenko, Ekaterina E. ;

Galenko, Alexey V. ;

Khlebnikov, Alexander F. ;

Novikov, Mikhail S. .

RSC ADVANCES, 2015, 5 (24) :18172-18176

[12] The Chemistry of Transition Metals with Three-Membered Ring Heterocycles [J].

Huang, Chung-Yang ;

Doyle, Abigail G. .

CHEMICAL REVIEWS, 2014, 114 (16) :8153-8198

[13]

Khlebnikov A.F., 2016, Top. Heterocycl. Chem, V41, P143, DOI 10.1007/7081_2015_154

[14] Recent advances in 2H-azirine chemistry [J].

Khlebnikov, Alexander F. ;

Novikov, Mikhail S. .

TETRAHEDRON, 2013, 69 (16) :3363-3401

[15] Ruthenium-Catalyzed [3+2] Cycloaddition of 2H-Azirines with Alkynes: Access to Polysubstituted Pyrroles [J].

Li, Tengfei ;

Yan, Hao ;

Li, Xincheng ;

Wang, Chunxiang ;

Wan, Boshun .

JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (23) :12031-12037

[16] Ruthenium-Catalyzed C-C Bond Cleavage of 2H-Azirines: A Formal [3+2+2] Cycloaddition to Fused Azepine Skeletons [J].

Li, Tengfei ;

Xu, Fen ;

Li, Xincheng ;

Wang, Chunxiang ;

Wan, Boshun .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (08) :2861-2865

[17] Enantioselective Reaction of 2H-Azirines with Phosphite Using Chiral Bis(imidazoline)/Zinc(II) Catalysts [J].

Nakamura, Shuichi ;

Hayama, Daiki .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (30) :8785-8789

[18] Base-Induced Transformation of 2-Acyl-3-alkyl-2H-azirines to Oxazoles: Involvement of Deprotonation-Initiated Pathways [J].

Ning, Yingtang ;

Otani, Yuko ;

Ohwada, Tomohiko .

JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (12) :6313-6326

[19]

Pinho, 2001, TETRAHEDRON, V57, P6203

[20] Metal-Catalyzed Isomerization of 5-Heteroatom-Substituted Isoxazoles as a New Route to 2-Halo-2 H -azirines [J].

Rostovskii, Nikolai V. ;

Agafonova, Anastasiya V. ;

Smetanin, Ilia A. ;

Novikov, Mikhail S. ;

Khlebnikov, Alexander F. ;

Ruvinskaya, Julia O. ;

Starova, Galina L. .

SYNTHESIS-STUTTGART, 2017, 49 (19) :4478-4488

← 1 2 3 →