Multicatalytic Beckmann rearrangement of 2-hydroxylarylketone oxime: Switchable synthesis of benzo[d]oxazoles and N-(2-hydroxylaryl)amides

被引：4

作者：

Li, Zhen ^{[1
]}

Fang, Chengtao ^{[1
]}

Zheng, Yannan ^{[1
]}

Qiu, Guanyinsheng ^{[1
]}

Li, Xiaofang ^{[2
]}

Zhou, Hongwei ^{[1
]}

机构：

[1] Jinxing Univ, Coll Biol Chem Sci & Engn, 118 Jiahang Rd, Jiaxing 314001, Peoples R China

[2] Hunan Univ Sci & Technol, Sch Chem & Chem Engn, Xiangtan 411201, Hunan, Peoples R China

来源：

TETRAHEDRON LETTERS | 2018年 / 59卷 / 44期

关键词：

Beckmann rearrangement; Switchable synthesis; Benzo[d]oxazoles; Multicatalysis; 2-Hydroxylarylketone oxime; CYANURIC CHLORIDE; IONIC LIQUIDS; KETOXIMES; DERIVATIVES; CATALYSTS; MILD; BENZOXAZOLES; CYCLIZATION;

D O I：

10.1016/j.tetlet.2018.09.043

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A switchable synthesis route is developed for benzo[d]oxazole derivatives and (2-hydroxylaryl)benzamide from 2-hydroxylbenzeneketoxime using organomolecules (BOP-Cl, and CNC) and Lewis acid cocatalyzed Beckmann rearrangement (BR) reaction. Further, this reaction is switched using different organocatalysts. (C) 2018 Elsevier Ltd. All rights reserved.

引用

页码：3934 / 3937

页数：4

共 40 条

[1] Mechanistic Insight into Self-Propagation of Organo-Mediated Beckmann Rearrangement: A Combined Experimental and Computational Study [J].

An, Na ;

Tian, Bo-Xue ;

Pi, Hong-Jun ;

Eriksson, Leif A. ;

Deng, Wei-Ping .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (09) :4297-4302

[2] Rhodium-catalyzed Beckmann rearrangement [J].

Arisawa, M ;

Yamaguchi, M .

ORGANIC LETTERS, 2001, 3 (02) :311-312

[3] Silica supported MoO3:: a mild heterogeneous catalyst for the Beckmann rearrangement and its application to some sugar derived ketoximes [J].

Dongare, MK ;

Bhagwat, VV ;

Ramana, CV ;

Gurjar, MK .

TETRAHEDRON LETTERS, 2004, 45 (24) :4759-4762

[4] Cyanuric chloride as a mild and active Beckmann rearrangement catalyst [J].

Furuya, Y ;

Ishihara, K ;

Yamamoto, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (32) :11240-11241

[5]

Ganguly N.C., 2010, Synthesis, V21, P3705

[6] Dichloroimidazolidinedione-Activated Beckmann Rearrangement of Ketoximes for Accessing Amides and Lactams [J].

Gao, Yu ;

Liu, Jingjing ;

Li, Zhenjiang ;

Guo, Tianfo ;

Xu, Songquan ;

Zhu, Hui ;

Wei, Fulan ;

Chen, Siming ;

Gebru, Hailemariam ;

Guo, Kai .

JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (04) :2040-2049

[7]

Gawley R.E., 1988, Organic Reactions, V35, P1, DOI DOI 10.1002/0471264180.OR035.01

[8] Beckmann rearrangement of ketoximes to lactams by triphosphazene catalyst [J].

Hashimoto, Masaharu ;

Obora, Yasushi ;

Sakaguchi, Satoshi ;

Ishii, Yasutaka .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (07) :2894-2897

[9] Synthesis of Skeletally Diverse and Stereochemically Complex Library Templates Derived from lsosteviol and Steviol [J].

Hutt, Oliver E. ;

Doan, Trinh L. ;

Georg, Gunda I. .

ORGANIC LETTERS, 2013, 15 (07) :1602-1605

[10] A simple, eco-friendly, and recyclable bi-functional acidic ionic liquid catalysts for Beckmann rearrangement [J].

Kore, Rajkumar ;

Srivastava, Rajendra .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2013, 376 :90-97

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