Ring opening [3+2] cyclization of azaoxyallyl cations with benzo[d]-isoxazoles: Efficient access to 2-hydroxyaryl-oxazolines

被引：24

作者：

He, Yicheng ^{[1
]}

Pi, Chao ^{[1
]}

Wu, Yangjie ^{[1
]}

Cui, Xiuling ^{[1
]}

机构：

[1] Zhengzhou Univ, Key Lab Appl Chem Henan Univ, Dept Chem, Henan Key Lab Chem Biol & Organ Chem, Zhengzhou 450052, Peoples R China

来源：

CHINESE CHEMICAL LETTERS | 2020年 / 31卷 / 02期

关键词：

Azaoxyallylic cations; Ring-opening; 3+2] Cycloaddition; 2-Hydroxyaryl-oxazolines; C similar to O 3-atom synthon; AZA-OXYALLYLIC CATIONS; ONE-POT SYNTHESIS; CYCLOADDITION REACTIONS; 1,3-DIPOLAR CYCLOADDITION; ANNULATION; ACID; TRANSFORMATION; CONSTRUCTION; DERIVATIVES; COMPLEXES;

D O I：

10.1016/j.cclet.2019.09.025

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A selective ring-opening [3 + 2] cyclization reaction of benzo[d]isoxazoles with 2-bromo-propanamides has been developed. The azaoxyallyl cation intermediates are employed as C similar to O 3-atom synthon to build oxa-heterocycles via the selectivity of suitable cyclization partners. This transformation provides rapid access to highly functionalized 2-hydroxyaryl-oxazolines under mild conditions and excellent regioselectivity. (C) 2019 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

引用

页码：396 / 400

页数：5

共 77 条

[1] Access to 4-Oxazolidinones: A (3+2) Cycloaddition Approach [J].

Acharya, Arjun ;

Montes, Karissa ;

Jeffrey, Christopher S. .

ORGANIC LETTERS, 2016, 18 (23) :6082-6085

[2] Dearomative Indole Cycloaddition Reactions of Aza-Oxyallyl Cationic Intermediates: Modular Access to Pyrroloindolines [J].

Acharya, Arjun ;

Anumandla, Devendar ;

Jeffrey, Christopher S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (47) :14858-14860

[3] Intramolecular Aza-[4+3] Cycloaddition Reactions of α-Halohydroxamates [J].

Acharya, Arjun ;

Eickhoff, John A. ;

Jeffrey, Christopher S. .

SYNTHESIS-STUTTGART, 2013, 45 (13) :1825-1836

[4] Base-controlled [3+3] cycloaddition of isoquinoline N-oxides with azaoxyallyl cations [J].

An, Yuanyuan ;

Xia, Hongguang ;

Wu, Jie .

CHEMICAL COMMUNICATIONS, 2016, 52 (68) :10415-10418

[5] Synthesis of Cyclopenta[b]piperazinones via an Azaoxyallyl Cation [J].

Balde, Boubacar ;

Force, Guillaume ;

Marin, Lucile ;

Guillot, Regis ;

Schulz, Emmanuelle ;

Gandon, Vincent ;

Leboeuf, David .

ORGANIC LETTERS, 2018, 20 (23) :7405-7409

[6] Trapping the elusive aza-oxyallylic cation: new opportunities in heterocycloaddition chemistry [J].

Barnes, Korry L. ;

Koster, Anna K. ;

Jeffrey, Christopher S. .

TETRAHEDRON LETTERS, 2014, 55 (34) :4690-4696

[7] Total synthesis of vulnibactin: A natural product iron chelator [J].

Bergeron, Raymond J. ;

Bharti, Neelam ;

Singh, Shailendra .

SYNTHESIS-STUTTGART, 2007, (07) :1033-1037

[8] SYNTHETIC STUDIES RELATED TO MYCOBACTINS .1. SYNTHESIS OF 2-(2'-HYDROXYPHENYL)-2-OXAZOLINE-4-CARBOXYLIC ACID AND RELATED COMPOUNDS [J].

BLACK, DSC ;

WADE, MJ .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1972, 25 (08) :1797-&

[9] Copper-Catalyzed Diversity-Oriented Synthesis (DOS) of 4-Amino-2H-chromen-2-imines: Application of Kemp Elimination toward O-Heterocycles [J].

Chen, Zhiyuan ;

Han, Cuifen ;

Fan, Congbin ;

Liu, Gang ;

Pu, Shouzhi .

ACS OMEGA, 2018, 3 (07) :8160-8168

[10] Transition-Metal Free Construction of Isoquinoline-fused Triazines Containing Alkenyl C-X Bonds [J].

Cheng, Xiao ;

Cao, Xia ;

Zhou, Shuang-Jing ;

Cai, Bao-Gui ;

He, Xiang-Kui ;

Xuan, Jun .

ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (06) :1230-1235

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