A New Pathway to 2-Arylbenzoxazoles and 2-Arylbenzothiazoles Via One-Pot Oxidative Cyclization Reactions Under Iron-Organic Framework Catalysis

作者: Son H Doan , Chau B Tran , An LN Cao , Nhan TH Le , Nam TS Phan

DOI: 10.1007/S10562-019-02747-1

关键词:

摘要: Iron-organic framework MOF-235 was synthesized, and consequently utilized as a productive heterogeneous catalyst for the synthesis of 2-arylbenzoxazoles 2-arylbenzothiazoles via one-pot oxidative cyclization reactions between 2-aminophenols or 2-aminothiophenols alcohols. The transformation considerably controlled by oxidant nature solvent, system di-tert-butylperoxide with xylene led to best yield major products. presented higher catalytic efficiency than number MOF-based catalysts established homogeneous catalysts. Recovering reutilizing possible while its activity retained. To our knowledge, this iron-catalyzed produce under catalysis conditions not previously reported in literature.

参考文章(53)
Khalid Bougrin, André Loupy, Mohamed Soufiaoui, Trois nouvelles voies de synthèse des dérivés 1,3-azoliques sous micro-ondes Tetrahedron. ,vol. 54, pp. 8055- 8064 ,(1998) , 10.1016/S0040-4020(98)00431-1
Fan Teng, Song Sun, Yan Jiang, Jin-Tao Yu, Jiang Cheng, Copper-catalyzed oxidative C(sp3)–H/N–H coupling of sulfoximines and amides with simple alkanes via a radical process Chemical Communications. ,vol. 51, pp. 5902- 5905 ,(2015) , 10.1039/C5CC00839E
Gunaganti Naresh, Ruchir Kant, Tadigoppula Narender, Molecular iodine promoted divergent synthesis of benzimidazoles, benzothiazoles, and 2-benzyl-3-phenyl-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazines. Journal of Organic Chemistry. ,vol. 79, pp. 3821- 3829 ,(2014) , 10.1021/JO5000797
Mansoor Anbia, Vahid Hoseini, Sara Sheykhi, SORPTION OF METHANE, HYDROGEN AND CARBON DIOXIDE ON METAL-ORGANIC FRAMEWORK, IRON TEREPHTHALATE (MOF-235) Journal of Industrial and Engineering Chemistry. ,vol. 18, pp. 1149- 1152 ,(2012) , 10.1016/J.JIEC.2012.01.014
Andrea C. Sudik, Adrien P. Côté, Omar M. Yaghi, Metal-Organic Frameworks Based on Trigonal Prismatic Building Blocks and the New “acs” Topology Inorganic Chemistry. ,vol. 44, pp. 2998- 3000 ,(2005) , 10.1021/IC050064G
Neelam P Prajapati, Rajesh H Vekariya, Mayuri A Borad, Hitesh D Patel, None, Recent advances in the synthesis of 2-substituted benzothiazoles: a review RSC Advances. ,vol. 4, pp. 60176- 60208 ,(2014) , 10.1039/C4RA07437H
I.A. Baburin, V.A. Blatov, L. Carlucci, G. Ciani, D.M. Proserpio, Interpenetrating metal-organic and inorganic 3D networks: a computer-aided systematic investigation. Part II [1]. Analysis of the Inorganic Crystal Structure Database (ICSD) Journal of Solid State Chemistry. ,vol. 178, pp. 2452- 2474 ,(2005) , 10.1016/J.JSSC.2005.05.029
Nicolai A. Aksenov, Alexander V. Aksenov, Oleg N. Nadein, Dmitrii A. Aksenov, Alexander N. Smirnov, Michael Rubin, One-pot synthesis of benzoxazoles via the metal-free ortho-C–H functionalization of phenols with nitroalkanes RSC Advances. ,vol. 5, pp. 71620- 71626 ,(2015) , 10.1039/C5RA15128G
Amarajothi Dhakshinamoorthy, Abdullah M Asiri, Hermenegildo Garcia, None, Metal-organic frameworks catalyzed C-C and C-heteroatom coupling reactions. Chemical Society Reviews. ,vol. 44, pp. 1922- 1947 ,(2015) , 10.1039/C4CS00254G