Facile synthesis of 2-benzoxazoles via CuI/2,2'-bipyridine catalyzed intramolecular C-O coupling of 2-haloanilides

被引:8
作者
Saranya, Thachora Venu [1 ]
Sruthi, Pambingal Rajan [1 ]
Anas, Saithalavi [1 ,2 ]
机构
[1] Mahatma Gandhi Univ, Sch Chem Sci, Kottayam 686560, Kerala, India
[2] Mahatma Gandhi Univ, Adv Mol Mat Res Ctr, Kottayam, Kerala, India
关键词
Benzoxazole; copper; 2-haloanilides; 2,2'-bipyridine; C-O coupling; BENZOXAZOLE DERIVATIVES; PARALLEL SYNTHESIS; BENZOTHIAZOLES; ANTITUMOR; ANTICANCER; ARYLATION; AGONIST; ANALOGS;
D O I
10.1080/00397911.2018.1554147
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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]
引用
收藏
页码:297 / 307
页数:11
相关论文
共 33 条
[1]  
Aggarwal N., 2017, Int. J. Pharm. Sci. Res, V2, P1, DOI DOI 10.1038/JA.2008.97
[2]   Synthesis and biological properties of benzothiazole, benzoxazole, and chromen-4-one analogues of the potent antitumor agent 2-(3,4-dimethoxyphenyl)-5-fluorobenzothiazole (PMX 610, NSC 721648) [J].
Aiello, Stefania ;
Wells, Geoffrey ;
Stone, Erica L. ;
Kadri, Hachemi ;
Bazzi, Rana ;
Bell, David R. ;
Stevens, Malcolm F. G. ;
Matthews, Charles S. ;
Bradshaw, Tracey D. ;
Westwell, Andrew D. .
JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (16) :5135-5139
[3]   Organocatalytic Syntheses of Benzoxazoles and Benzothiazoles using Aryl Iodide and Oxone via C-H Functionalization and C-O/S Bond Formation [J].
Alla, Santhosh Kumar ;
Sadhu, Pradeep ;
Punniyamurthy, Tharmalingam .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (16) :7502-7511
[4]   Copper-catalysed intramolecular O-arylation of aryl chlorides and bromides:: a straightforward approach to benzo[d]oxazoles in water [J].
Barbero, Nekane ;
Carril, Monica ;
SanMartin, Raul ;
Dominguez, Esther .
TETRAHEDRON, 2007, 63 (42) :10425-10432
[5]   Functionalized Orthoesters as Powerful Building Blocks for the Efficient Preparation of Heteroaromatic Bicycles [J].
Bastug, Gulluzar ;
Eviolitte, Christophe ;
Marko, Istvan E. .
ORGANIC LETTERS, 2012, 14 (13) :3502-3505
[6]   Difluoromethylbenzoxazole Pyrimidine Thioether Derivatives: A Novel Class of Potent Non-Nucleoside HIV-1 Reverse Transcriptase Inhibitors [J].
Boyer, Jeremie ;
Arnoult, Eric ;
Medebielle, Maurice ;
Guillemont, Jerome ;
Unge, Johan ;
Jochmans, Dirk .
JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (23) :7974-7985
[7]   Synthesis, structure-activity relationships, and antitumor studies of 2-benzoxazolyl hydrazones derived from alpha-(N)-acyl heteroaromatics [J].
Easmon, Johnny ;
Purstinger, Gerhard ;
Thies, Katrin-Sofia ;
Heinisch, Gottfried ;
Hofmann, Johann .
JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (21) :6343-6350
[8]   Parallel synthesis of a library of benzoxazoles and benzothiazoles using ligand-accelerated copper-catalyzed cyclizations of ortho-halobenzanilides [J].
Evindar, G ;
Batey, RA .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (05) :1802-1808
[9]   Ruthenium-Catalyzed Synthesis of Benzoxazoles Using Acceptor less Dehydrogenative Coupling Reaction of Primary Alcohols with 2-Aminophenol under Heterogeneous Conditions [J].
Khalafi-Nezhad, Ah ;
Panahi, Farhad .
ACS CATALYSIS, 2014, 4 (06) :1686-1692
[10]   Divergent reactivities of o-haloanilides with CuO nanoparticles in water: a green synthesis of benzoxazoles and o-hydroxyanilides [J].
Khatun, Nilufa ;
Guin, Srimanta ;
Rout, Saroj Kumar ;
Patel, Bhisma K. .
RSC ADVANCES, 2014, 4 (21) :10770-10778