Development of newer methods for the synthesis of Benzoxazoles has of greater interest due to their wide range of biological activities and pharmaceutical importance. We herein report a facile and general method for the synthesis of 2-substituted Benzoxazoles via copper catalyzed intramolecular C-O cross-coupling of 2-haloanilides. A combination of CuI (5 mol%), 2,2'-bipyridine (10 mol%), Cs2CO3 (2 equiv.) in DMF solvent with 4 angstrom molecular sieves at 140 degrees C, illustrated the scope for tuning the reactivity of 2-haloanilides toward the selective formation of a series of 2-alkyl benzoxazole derivatives in moderate to good yields. This is the first systematic study using CuI/2,2'-Bipyridine as the catalytic system for the synthesis of 2-substituted Benzoxazoles. The outcome of the reaction was found to be significantly influenced by the aromatic and amide substituents of 2-haloanilides. [GRAPHICS]
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[1]
Aggarwal N., 2017, Int. J. Pharm. Sci. Res, V2, P1, DOI DOI 10.1038/JA.2008.97
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Euskal Herriko Unib, Zien Tecknol Fak, Kim Organ II Saila, Bilbao 48080, SpainEuskal Herriko Unib, Zien Tecknol Fak, Kim Organ II Saila, Bilbao 48080, Spain
Barbero, Nekane
;
Carril, Monica
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Euskal Herriko Unib, Zien Tecknol Fak, Kim Organ II Saila, Bilbao 48080, SpainEuskal Herriko Unib, Zien Tecknol Fak, Kim Organ II Saila, Bilbao 48080, Spain
Carril, Monica
;
SanMartin, Raul
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Euskal Herriko Unib, Zien Tecknol Fak, Kim Organ II Saila, Bilbao 48080, SpainEuskal Herriko Unib, Zien Tecknol Fak, Kim Organ II Saila, Bilbao 48080, Spain
SanMartin, Raul
;
Dominguez, Esther
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Euskal Herriko Unib, Zien Tecknol Fak, Kim Organ II Saila, Bilbao 48080, SpainEuskal Herriko Unib, Zien Tecknol Fak, Kim Organ II Saila, Bilbao 48080, Spain
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Univ Lyon 1, ICBMS, UMR CNRS UCBL INSA, Equipe Synth Mol Interet Therapeut SMITH, F-69622 Villeurbanne, FranceUniv Lyon 1, ICBMS, UMR CNRS UCBL INSA, Equipe Synth Mol Interet Therapeut SMITH, F-69622 Villeurbanne, France
Boyer, Jeremie
;
Arnoult, Eric
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Janssen Cilag Tibotec, Chem Lead Antimicrobial Res, F-27106 Val De Reuil, FranceUniv Lyon 1, ICBMS, UMR CNRS UCBL INSA, Equipe Synth Mol Interet Therapeut SMITH, F-69622 Villeurbanne, France
Arnoult, Eric
;
Medebielle, Maurice
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Univ Lyon 1, ICBMS, UMR CNRS UCBL INSA, Equipe Synth Mol Interet Therapeut SMITH, F-69622 Villeurbanne, FranceUniv Lyon 1, ICBMS, UMR CNRS UCBL INSA, Equipe Synth Mol Interet Therapeut SMITH, F-69622 Villeurbanne, France
Medebielle, Maurice
;
Guillemont, Jerome
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Janssen Cilag Tibotec, Chem Lead Antimicrobial Res, F-27106 Val De Reuil, FranceUniv Lyon 1, ICBMS, UMR CNRS UCBL INSA, Equipe Synth Mol Interet Therapeut SMITH, F-69622 Villeurbanne, France
Guillemont, Jerome
;
Unge, Johan
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Lund Univ, MAX Lab, SE-22100 Lund, SwedenUniv Lyon 1, ICBMS, UMR CNRS UCBL INSA, Equipe Synth Mol Interet Therapeut SMITH, F-69622 Villeurbanne, France
Unge, Johan
;
Jochmans, Dirk
论文数: 0引用数: 0
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Tibotec Virco BVBA, BE-2340 Beerse, BelgiumUniv Lyon 1, ICBMS, UMR CNRS UCBL INSA, Equipe Synth Mol Interet Therapeut SMITH, F-69622 Villeurbanne, France
机构:
Euskal Herriko Unib, Zien Tecknol Fak, Kim Organ II Saila, Bilbao 48080, SpainEuskal Herriko Unib, Zien Tecknol Fak, Kim Organ II Saila, Bilbao 48080, Spain
Barbero, Nekane
;
Carril, Monica
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机构:
Euskal Herriko Unib, Zien Tecknol Fak, Kim Organ II Saila, Bilbao 48080, SpainEuskal Herriko Unib, Zien Tecknol Fak, Kim Organ II Saila, Bilbao 48080, Spain
Carril, Monica
;
SanMartin, Raul
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Euskal Herriko Unib, Zien Tecknol Fak, Kim Organ II Saila, Bilbao 48080, SpainEuskal Herriko Unib, Zien Tecknol Fak, Kim Organ II Saila, Bilbao 48080, Spain
SanMartin, Raul
;
Dominguez, Esther
论文数: 0引用数: 0
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机构:
Euskal Herriko Unib, Zien Tecknol Fak, Kim Organ II Saila, Bilbao 48080, SpainEuskal Herriko Unib, Zien Tecknol Fak, Kim Organ II Saila, Bilbao 48080, Spain
机构:
Univ Lyon 1, ICBMS, UMR CNRS UCBL INSA, Equipe Synth Mol Interet Therapeut SMITH, F-69622 Villeurbanne, FranceUniv Lyon 1, ICBMS, UMR CNRS UCBL INSA, Equipe Synth Mol Interet Therapeut SMITH, F-69622 Villeurbanne, France
Boyer, Jeremie
;
Arnoult, Eric
论文数: 0引用数: 0
h-index: 0
机构:
Janssen Cilag Tibotec, Chem Lead Antimicrobial Res, F-27106 Val De Reuil, FranceUniv Lyon 1, ICBMS, UMR CNRS UCBL INSA, Equipe Synth Mol Interet Therapeut SMITH, F-69622 Villeurbanne, France
Arnoult, Eric
;
Medebielle, Maurice
论文数: 0引用数: 0
h-index: 0
机构:
Univ Lyon 1, ICBMS, UMR CNRS UCBL INSA, Equipe Synth Mol Interet Therapeut SMITH, F-69622 Villeurbanne, FranceUniv Lyon 1, ICBMS, UMR CNRS UCBL INSA, Equipe Synth Mol Interet Therapeut SMITH, F-69622 Villeurbanne, France
Medebielle, Maurice
;
Guillemont, Jerome
论文数: 0引用数: 0
h-index: 0
机构:
Janssen Cilag Tibotec, Chem Lead Antimicrobial Res, F-27106 Val De Reuil, FranceUniv Lyon 1, ICBMS, UMR CNRS UCBL INSA, Equipe Synth Mol Interet Therapeut SMITH, F-69622 Villeurbanne, France
Guillemont, Jerome
;
Unge, Johan
论文数: 0引用数: 0
h-index: 0
机构:
Lund Univ, MAX Lab, SE-22100 Lund, SwedenUniv Lyon 1, ICBMS, UMR CNRS UCBL INSA, Equipe Synth Mol Interet Therapeut SMITH, F-69622 Villeurbanne, France
Unge, Johan
;
Jochmans, Dirk
论文数: 0引用数: 0
h-index: 0
机构:
Tibotec Virco BVBA, BE-2340 Beerse, BelgiumUniv Lyon 1, ICBMS, UMR CNRS UCBL INSA, Equipe Synth Mol Interet Therapeut SMITH, F-69622 Villeurbanne, France