Copper-Catalyzed Synthesis of Dibenzo[b,f]imidazo[1,2-d][1,4]oxazepine Derivatives via a Double Ullmann Coupling Reaction

Abstract

A double Ullmann coupling reaction successfully takes place between 4,5-diaryl-2-(2-bromophenyl)-1H-imidazoles and 2-bromophenols in the presence of Cs₂CO₃. This procedure is catalyzed by copper(I) iodide and o-phenanthroline and provides an efficient method for the synthesis of dibenzo[b,f]imidazo[1,2-d][1,4]oxazepine derivatives in good yields.

Key words

Ullmann coupling - dibenzoimidazo[1,4]oxazepines - copper(I) iodide - o-phenanthroline - catalysis

• References

• 1 Kathiravan PR, Muthukumaran S, Dhatchanamoorthy N, Shanmuganathan T, Venugopal M. Lett. Org. Chem. 2018; 15: 314
• 2 Yang J, Yang S.-M, Zhou S.-S, Lu D.-B, Ji L.-Y, Li Z.-J, Yu S.-W, Meng XB. Eur. J. Med. Chem. 2016; 122: 488
• 3a Huang DW, Huang L, Zhang Q.-W, Li J.-Q. Eur. J. Med. Chem. 2017; 140: 212
• 3b Wang Y.-Q, Wei Z, Zhu C.-Q, Ren Y.-Y, Wu C.-R. Tetrahedron 2016; 72: 4643
• 3c Sun M, Zhao J, Chen X.-F, Zong Z.-W, Han J.-Y, Du Y.-G, Sun H.-L, Wang F.-D. Bioorg. Med. Chem. Lett. 2016; 26: 4842
• 4 Nair MD, Desai JA. Indian J. Chem., Sect. B 1980; 19: 338
• 5 Tsvelikhovsky D, Buchwald SL. J. Am. Chem. Soc. 2011; 133: 14228
• 6a Zaware N, Ohlmeyer M. Heterocycl. Commun. 2014; 20: 251
• 6b Zhang Y, Liu J.-Q, Wang X.-S. Org. Biomol. Chem. 2018; 16: 1679
• 6c Lode DM, Sukowski V, Vila C, Munoz MC, Pedro JR. Org. Chem. Front. 2017; 4: 1624
• 6d Feng J.-B, Wu X.-F. Green Chem. 2015; 17: 4522
• 6e Sang P, Yu M, Tu H.-F, Zhang Y.-H. Chem. Commun. 2013; 49: 701
• 6f Yang Q, Cao H, Robertson A, Alper H. J. Org. Chem. 2010; 75: 6297
• 6g Chen Y, Peng Q, Zhang R, Hu J, Zhou Y, Xu L, Pan X. Synlett 2017; 28: 1201
• 6h Lluna-Galán C, Blay G, Fernández I, Muñoz MC, Pedro JR, Vila C. Adv. Synth. Catal. 2018; 360: 3662
• 6i More GV, Bhanage BM. Org. Biomol. Chem. 2017; 15: 5263
• 6j Sapegin A, Reutskaya E, Smirnov A, Korsakov M, Krasavin M. Tetrahedron Lett. 2016; 57: 5877
• 6k Hu F, Liu H, Jia J, Ma C. Org. Biomol. Chem. 2016; 14: 11076
• 6l Zhu C.-Q, Deng Z.-F, Zhang Y, Wang Y.-Q. Org. Chem. Front. 2017; 4: 196
• 7 Mahdavi M, Hariri R, Saeedi M, Foroumadi A, Shafiee A, Akbarzadeh T. Tetrahedron Lett. 2015; 56: 7082
• 8a Kelly SM, Han C, Tung L, Gosselin F. Org. Lett. 2017; 19: 3021
• 8b Wei JJ, Song WB, Zhu YF, Wei BL, Xuan LJ. Tetrahedron 2018; 74: 19
• 8c Bollenbach M, Aquino PG. V, de Araújo-Júnior JX, Bourguignon J.-J, Bihel F, Salomé C, Wagner P, Schmitt M. Chem. Eur. J. 2017; 23: 13676
• 8d Zhao X, She Y, Fang K, Li G. J. Org. Chem. 2017; 82: 1024
• 8e Ziegler DT, Choi J, Muñoz-Molina JM, Bissember AC, Peters JC, Fu GC. J. Am. Chem. Soc. 2013; 135: 13107
• 8f Mai S, Zhao Y, Song Q. Org. Biomol. Chem. 2016; 14: 8685
• 9a Yang S, Wu C, Zhou H, Yang Y, Zhao Y, Wang C, Yang W, Xu J. Adv. Synth. Catal. 2013; 355: 53
• 9b Shi J, Wu J, Cui C, Dai W. J. Org. Chem. 2016; 81: 10392
• 9c Liu YW, Zhao F, Zhou HH, Xie K, Jiang YB. J. Chem. Sci. 2017; 129: 289
• 9d Chen D, Yuan D, Zhang C, Wu H, Zhang J, Li B, Zhu X. J. Org. Chem. 2017; 82: 10920
• 9e Hayato S, Tetsu T, Yoshitaka K, Hiromi U. Tetrahedron Lett. 2017; 58: 1015
• 9f Parveen I, Ahmed N. Tetrahedron Lett. 2017; 58: 2302
• 10a Ullmann F, Bielecki J. Ber. Dtsch. Chem. Ges. 1901; 34: 2174
• 10b Ullmann F. Ber. Dtsch. Chem. Ges. 1903; 36: 2382
• 11a Li C, Zhang W.-T, Wang X.-S. J. Org. Chem. 2014; 79: 5847
• 11b Chen D.-S, Dou G.-L, Li Y.-L, Liu Y, Wang X.-S. J. Org. Chem. 2013; 78: 5700
• 11c Ma Y.-G, Huang M.-Q, Liu Z, Liu J.-Q, Wang X.-S. J. Org. Chem. 2018; 83: 9504
• 11d Ma Y.-G, Li C, Yao C.-S, Wang X.-S. Tetrahedron 2016; 72: 3844
• 12 Azizi N, Dado N, Amiri AK. Can. J. Chem. 2012; 90: 195