A novel strategy for the construction of substituted benzoxazoles via a tandem oxidative process

被引:44
作者
Gu, Lijun [1 ,2 ]
Jin, Cheng [3 ]
Guo, Junming [1 ,2 ]
Zhang, Lizhu [1 ,2 ]
Wang, Wei [1 ,2 ]
机构
[1] Yunnan Univ Nationalities, Key Lab Chem Ethn Med Resources, State Ethn Affairs Commiss, Kunming 650500, Yunnan, Peoples R China
[2] Yunnan Univ Nationalities, Minist Educ, Kunming 650500, Yunnan, Peoples R China
[3] Changzhou Tianma Grp Co Ltd, Changzhou 213127, Jiangsu, Peoples R China
关键词
C-C BOND; MICROWAVE-ASSISTED SYNTHESIS; DIRECT FUNCTIONALIZATION; IRON; ADJACENT; 2-ARYLBENZOXAZOLES; HETEROARENES; ANNULATION; ARYLATION; ACID;
D O I
10.1039/c3cc46375c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A practical and simple synthesis of benzoxazoles from easily available substrates was developed. The protocol is triggered by an iron-catalyzed tandem oxidative process from simple toluene derivatives and 2-aminophenols. This method represents a straightforward approach to access substituted benzoxazoles.
引用
收藏
页码:10968 / 10970
页数:3
相关论文
共 47 条
[1]   Palladium-Catalyzed Direct Arylations of Heteroarenes with Tosylates and Mesylates [J].
Ackermann, Lutz ;
Althammer, Andreas ;
Fenner, Sabine .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (01) :201-204
[2]   A domino copper-catalyzed C-N and C-O cross-coupling for the conversion of primary amides into benzoxazoles [J].
Altenhoff, G ;
Glorius, F .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (13-15) :1661-1664
[3]   One-pot preparation of 2-(Alkyl)arylbenzothiazoles from the corresponding o-halobenzanilides [J].
Bernardi, Dan ;
Ba, Lalla Aiecha ;
Kirsch, Gilbert .
SYNLETT, 2007, (13) :2121-2123
[4]   Hypervalent iodine mediated intramolecular cyclization of thioformanilides: Expeditious approach to 2-substituted benzothiazoles [J].
Bose, D. Subhas ;
Idrees, Mohd. .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (21) :8261-8263
[5]   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
[6]   Discovery of 2-Arylbenzoxazoles as Upregulators of Utrophin Production for the Treatment of Duchenne Muscular Dystrophy [J].
Chancellor, Daniel R. ;
Davies, Kay E. ;
De Moor, Olivier ;
Dorgan, Colin R. ;
Johnson, Peter D. ;
Lambert, Adam G. ;
Lawrence, Daniel ;
Lecci, Cristina ;
Maillol, Carole ;
Middleton, Penny J. ;
Nugent, Gary ;
Poignant, Severine D. ;
Potter, Allyson C. ;
Price, Paul D. ;
Pye, Richard J. ;
Storer, Richard ;
Tinsley, Jonathon M. ;
van Well, Renate ;
Vickers, Richard ;
Vile, Julia ;
Wilkes, Fraser J. ;
Wilson, Francis X. ;
Wren, Stephen P. ;
Wynne, Graham M. .
JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (09) :3241-3250
[7]   Cyanide as a powerful catalyst for facile synthesis of benzofused heteroaromatic compounds via aerobic oxidation [J].
Cho, Yeon-Ho ;
Lee, Chun-Young ;
Cheon, Cheol-Hong .
TETRAHEDRON, 2013, 69 (32) :6565-6573
[8]   Iron-catalyzed trifluoromethylation with concomitant C-C bond formation via 1,2-migration of an aryl group [J].
Egami, Hiromichi ;
Shimizu, Ryo ;
Usui, Yoshihiko ;
Sodeoka, Mikiko .
CHEMICAL COMMUNICATIONS, 2013, 49 (66) :7346-7348
[9]   Novel Synthetic Route to a-Aminophosphonates Containing Benzothiazole Moiety [J].
Gu Liju ;
Wang Rui ;
Huang Xiangzhong ;
Jin Cheng .
CHINESE JOURNAL OF CHEMISTRY, 2012, 30 (10) :2483-2487
[10]   Microwave-Assisted Synthesis of Ethyl 1,3-Disubstituted-1,6-dihydropyrrolo[2,3-c]pyrazole-5-carboxylates [J].
Gu, Lijun ;
Li, Xiangguang .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2013, 50 (02) :408-412