Synthesis of Imidazo[1,2-f]phenanthridines through Palladium-Catalyzed Intramolecular C–C Bond Formation

Abstract

A simple and convenient approach is developed for the synthesis of the imidazo[1,2-f]phenanthridine framework via post-functionalization of imidazoles obtained through four-component reactions of 1,2-dicarbonyl compounds, anilines, aldehydes and ammonium acetate. The methodology involves palladium-catalyzed direct arylation through sp² C–H activation. The reported procedure delivers good to high yields of imidazo[1,2-f]phenanthridine derivatives (58–94%) starting from readily available precursors.

Key words

C–H activation - C–C bond formation - direct arylation - palladium catalysis - imidazo[1,2-f]phenanthridines

• References

• 1 Alberico D, Scott ME, Lautens M. Chem. Rev. 2007; 107: 174
• 2a Yan L, Zhao D, Lan J, Cheng Y, Guo Q, Li X, Wu N, You J. Org. Biomol. Chem. 2013; 11: 7966
• 2b Pisula W, Dierschke F, Mullen K. J. Mater. Chem. 2006; 16: 4058
• 2c Chen C, Shang G, Zhou J, Yu Y, Li B, Peng J. Org. Lett. 2014; 16: 1872
• 2d Lee D.-H, Park T.-Y, Bae J.-S, Nam H, Jang J.-G, Hong S.-K. WO2010062065, 2010
• 3 Liu J, Zhang N, Yue Y, Liu G, Liu R, Zhang Y, Zhuo K. Eur. J. Org. Chem. 2013; 7683
• 4 Grimshaw J, Grimshaw JT. Tetrahedron Lett. 1975; 16: 2601
• 5 Pipe DF, Rees CW. J. Chem. Soc., Chem. Commun. 1982; 520
• 6a Parenty AD. C, Song Y.-F, Richmond CJ, Cronin L. Org. Lett. 2007; 9: 2253
• 6b Liao Q, Zhang L, Li S, Xi C. Org. Lett. 2011; 13: 228
• 6c Parenty AD. C, Cronin L. Synthesis 2008; 155
• 6d Parenty AD. C, Cronin L. Synthesis 2008; 1479
• 6e Houghton PG, Pipe DF, Rees CW. J. Chem. Soc., Perkin Trans. 1 1985; 1471
• 6f Parenty AD. C, Guthrie KM, Song Y.-F, Smith LV, Burkholder E, Cronin L. Chem. Commun. 2006; 1194
• 6g Xie C, Zhang Y, Huang Z, Xu P. J. Org. Chem. 2007; 72: 5431
• 6h Liu Z, Larock RC. J. Org. Chem. 2006; 72: 223
• 7a Roy B, De R, Hazra S. Monatsh. Chem. 2012; 143: 119
• 7b Čerňa I, Pohl R, Klepetářová B, Hocek M. J. Org. Chem. 2010; 75: 2302
• 8 Takeda D, Hirano K, Satoh T, Miura M. Heterocycles 2012; 86: 487
• 9 Sunderhaus JD, Martin SF. Chem. Eur. J. 2009; 15: 1300
• 10a Tyagi V, Khan S, Bajpai V, Gauniyal HM, Kumar B, Chauhan PM. S. J. Org. Chem. 2012; 77: 1414
• 10b Kumar A, Li Z, Sharma SK, Parmar VS, Van der Eycken EV. Chem. Commun. 2013; 49: 6803
• 11a Bonnaterre F, Bois-Choussy M, Zhu J. Beilstein J. Org. Chem. 2008; 4: 10
• 11b Ma Z, Xiang Z, Luo T, Lu K, Xu Z, Chen J, Yang Z. J. Comb. Chem. 2006; 8: 696
• 11c Sun H, Zhou H, Khorev O, Jiang R, Yu T, Wang X, Du Y, Ma Y, Meng T, Shen J. J. Org. Chem. 2012; 77: 10745
• 11d El Akkaoui A, Hiebel M.-A, Mouaddib A, Berteina-Raboin S, Guillaumet G. Tetrahedron 2012; 68: 9131
• 11e Yan H, Yan R, Yang S, Gao X, Wang Y, Huang G, Liang Y. Chem. Asian J. 2012; 7: 2028
• 11f Yang A, Jiang R, Khorev O, Yu T, Zhang Y, Ma L, Chen G, Shen J, Meng T. Adv. Synth. Catal. 2013; 355: 1984
• 11g Wang Y, Frett B, Li H.-y. Org. Lett. 2014; 16: 3016
• 11h Yan H, Wang Y, Pan C, Zhang H, Yang S, Ren X, Li J, Huang G. Eur. J. Org. Chem. 2014; 2754
• 12a Pericherla K, Khedar P, Khungar B, Kumar A. Chem. Commun. 2013; 49: 2924
• 12b Pericherla K, Jha A, Khungar B, Kumar A. Org. Lett. 2013; 15: 4304
• 12c Pericherla K, Kaswan P, Khedar P, Khungar B, Parang K, Kumar A. RSC Adv. 2013; 3: 18923
• 12d Dhiman S, Pericherla K, Nandwana NK, Kumar D, Kumar A. J. Org. Chem. 2014; 79: 7399
• 13a Lyons TW, Sanford MS. Chem. Rev. 2010; 110: 1147
• 13b Ackermann L. Chem. Rev. 2011; 111: 1315
• 14a Lafrance M, Lapointe D, Fagnou K. Tetrahedron 2008; 64: 6015
• 14b Peng J, Shang G, Chen C, Miao Z, Li B. J. Org. Chem. 2012; 78: 1242
• 14c Wesch T, Berthelot-Bréhier A, Leroux FR, Colobert F. Org. Lett. 2013; 15: 2490
• 14d Rong L, Liu Q, Shi Y, Tang J. Chem. Commun. 2011; 47: 2155
• 14e Gao J, Shao Y, Zhu J, Zhu J, Mao H, Wang X, Lv X. J. Org. Chem. 2014; 79: 9000
• 14f Wang C, Piel I, Glorius F. J. Am. Chem. Soc. 2009; 131: 4194
• 15a Samai S, Nandi GC, Singh P, Singh MS. Tetrahedron 2009; 65: 10155
• 15b Moosavi-Zare AR, Asgari Z, Zare A, Zolfigol MA, Shekouhy M. RSC Adv. 2014; 4: 60636
• 15c Balalaie S, Arabanian A. Green Chem. 2000; 2: 274
• 15d Sharma RK, Sharma C Prerna Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2012; 51: 1489
• 15e Hasaninejad A, Zare A, Shekouhy M, Ameri Rad J. J. Comb. Chem. 2010; 12: 844
• 15f Heravi MM, Derikvand F, Bamoharram FF. J. Mol. Catal. A: Chem. 2007; 263: 112
• 15g Kantevari S, Vuppalapati SV. N, Biradar DO, Nagarapu L. J. Mol. Catal. A: Chem. 2007; 266: 109
• 15h Das Sharma S, Hazarika P, Konwar D. Tetrahedron Lett. 2008; 49: 2216
• 16a Hennessy EJ, Buchwald SL. J. Am. Chem. Soc. 2003; 125: 12084
• 16b González JJ, García N, Gómez-Lor B, Echavarren AM. J. Org. Chem. 1997; 62: 1286
• 16c Piou T, Neuville L, Zhu J. Org. Lett. 2012; 14: 3760
• 16d García-Cuadrado D, Braga AA. C, Maseras F, Echavarren AM. J. Am. Chem. Soc. 2006; 128: 1066