One-pot tandem synthesis of 2-arylbenzoxazole derivatives via copper-catalyzed C-N and C-O bond formation

Veerababurao Kavala; Donala Janreddy; Mustafa J. Raihan; Chun Wei Kuo; Chintakunta Ramesh; Ching Fa Yao

doi:10.1002/adsc.201200164

One-pot tandem synthesis of 2-arylbenzoxazole derivatives via copper-catalyzed C-N and C-O bond formation

Veerababurao Kavala, Donala Janreddy, Mustafa J. Raihan, Chun Wei Kuo, Chintakunta Ramesh, Ching Fa Yao^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

34 Citations (Scopus)

Abstract

The reaction of 2-(2-halophenyl)halobenzamides with a series of nitrogen nucleophiles resulted in the formation of benzoxazole derivatives. This procedure involves copper-catalyzed one-pot tandem C-N/C-O coupling reactions. No ligand was used in the reaction, even in the cases of primary or secondary amides, which were used as N-nucleophiles. However, L-proline was used as ligand in the case of N-aromatic heterocycles like indole, imidazole and pyrazole derivatives.

Original language	English
Pages (from-to)	2229-2240
Number of pages	12
Journal	Advanced Synthesis and Catalysis
Volume	354
Issue number	11-12
DOIs	https://doi.org/10.1002/adsc.201200164
Publication status	Published - 2012 Aug 13

Keywords

C-heteroatom bond formation
benzoxazoles
copper
ligand-free conditions
tandem reactions

ASJC Scopus subject areas

Catalysis
Organic Chemistry

Access to Document

10.1002/adsc.201200164

Cite this

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title = "One-pot tandem synthesis of 2-arylbenzoxazole derivatives via copper-catalyzed C-N and C-O bond formation",

abstract = "The reaction of 2-(2-halophenyl)halobenzamides with a series of nitrogen nucleophiles resulted in the formation of benzoxazole derivatives. This procedure involves copper-catalyzed one-pot tandem C-N/C-O coupling reactions. No ligand was used in the reaction, even in the cases of primary or secondary amides, which were used as N-nucleophiles. However, L-proline was used as ligand in the case of N-aromatic heterocycles like indole, imidazole and pyrazole derivatives.",

keywords = "C-heteroatom bond formation, benzoxazoles, copper, ligand-free conditions, tandem reactions",

author = "Veerababurao Kavala and Donala Janreddy and Raihan, {Mustafa J.} and Kuo, {Chun Wei} and Chintakunta Ramesh and Yao, {Ching Fa}",

year = "2012",

month = aug,

day = "13",

doi = "10.1002/adsc.201200164",

language = "English",

volume = "354",

pages = "2229--2240",

journal = "Advanced Synthesis and Catalysis",

issn = "1615-4150",

publisher = "Wiley-VCH Verlag",

number = "11-12",

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TY - JOUR

T1 - One-pot tandem synthesis of 2-arylbenzoxazole derivatives via copper-catalyzed C-N and C-O bond formation

AU - Kavala, Veerababurao

AU - Janreddy, Donala

AU - Raihan, Mustafa J.

AU - Kuo, Chun Wei

AU - Ramesh, Chintakunta

AU - Yao, Ching Fa

PY - 2012/8/13

Y1 - 2012/8/13

N2 - The reaction of 2-(2-halophenyl)halobenzamides with a series of nitrogen nucleophiles resulted in the formation of benzoxazole derivatives. This procedure involves copper-catalyzed one-pot tandem C-N/C-O coupling reactions. No ligand was used in the reaction, even in the cases of primary or secondary amides, which were used as N-nucleophiles. However, L-proline was used as ligand in the case of N-aromatic heterocycles like indole, imidazole and pyrazole derivatives.

AB - The reaction of 2-(2-halophenyl)halobenzamides with a series of nitrogen nucleophiles resulted in the formation of benzoxazole derivatives. This procedure involves copper-catalyzed one-pot tandem C-N/C-O coupling reactions. No ligand was used in the reaction, even in the cases of primary or secondary amides, which were used as N-nucleophiles. However, L-proline was used as ligand in the case of N-aromatic heterocycles like indole, imidazole and pyrazole derivatives.

KW - C-heteroatom bond formation

KW - benzoxazoles

KW - copper

KW - ligand-free conditions

KW - tandem reactions

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U2 - 10.1002/adsc.201200164

DO - 10.1002/adsc.201200164

M3 - Article

AN - SCOPUS:84865042229

SN - 1615-4150

VL - 354

SP - 2229

EP - 2240

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 11-12

ER -

One-pot tandem synthesis of 2-arylbenzoxazole derivatives via copper-catalyzed C-N and C-O bond formation

Abstract

Keywords

ASJC Scopus subject areas

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CCDC 869088: Experimental Crystal Structure Determination

CCDC 869323: Experimental Crystal Structure Determination

CCDC 869090: Experimental Crystal Structure Determination

Cite this

One-pot tandem synthesis of 2-arylbenzoxazole derivatives via copper-catalyzed C-N and C-O bond formation

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 869088: Experimental Crystal Structure Determination

CCDC 869323: Experimental Crystal Structure Determination

CCDC 869090: Experimental Crystal Structure Determination

Cite this