Modular Synthesis of Quinazolinone-Fused Phenanthridinones by a Palladium-Catalyzed Cascade C–H/N–H Arylation Process

Abstract

An efficient palladium-catalyzed protocol for the tandem synthesis of quinazolinone-fused phenanthridinones from 2-aryl­quinazolinones and o-dihaloarenes is described. This reaction sequence comprises direct intermolecular C–H arylation of 2-arylquinazolinones followed by an intramolecular aryl amidation reaction, affording 14H-quinazolino[3,2-f]phenanthridin-14-one derivatives in moderate to good yields.

Key words

palladium - C–H arylation - amidation - tandem reactions - ring-fused quinazolinones

• References

• 1a Mhaske SB, Argade NP. Tetrahedron 2006; 62: 9787
• 1b Kshirsagar UA. Org. Biomol. Chem. 2015; 13: 9336
• 2 Sharma PC, Kaur G, Pahwa R, Sharma A, Rajak H. Curr. Med. Chem. 2011; 18: 4786
• 3a Padala SR, Padi PR, Thipireddy V. Heterocycles 2003; 60: 183
• 3b Witt A, Bergman J. Curr. Org. Chem. 2003; 7: 659
• 3c Ma Z, Hano Y, Nomura T. Heterocycles 2005; 65: 2203
• 3d Connolly DJ, Cusack D, O’Sullivan TP, Guiry PJ. Tetrahedron 2005; 61: 10153
• 3e Demeunynck M, Baussanne I. Curr. Med. Chem. 2013; 20: 794
• 3f Khan I, Ibrar A, Abbas N, Saeed A. Eur. J. Med. Chem. 2014; 76: 193
• 3g He L, Li H, Chen J, Wu X.-F. RSC Adv. 2014; 4: 12065
• 3h Khan I, Ibrar A, Abbas N, Saeed A. Eur. J. Med. Chem. 2015; 90: 124
• 3i Abdou IM, Al-Neyadi SS. Heterocycl. Commun. 2015; 21: 115

For recent reviews, see:
• 4a Ohno H. Asian J. Org. Chem. 2013; 2: 18
• 4b Chiusoli GP, Catellani M, Costa M, Motti E, Della Ca’ N, Maestri G. Coord. Chem. Rev. 2010; 254: 456
• 4c Lyons TW, Sanford MS. Chem. Rev. 2010; 110: 1147
• 5a Sun J, Tan Q, Yang W, Liu B, Xu B. Adv. Synth. Catal. 2014; 356: 388
• 5b Liu M, Shu M, Yao C, Yin G, Wang D, Huang J. Org. Lett. 2016; 18: 824
• 6 Tilley JW, Coffen DL, Schaer BH, Lind J. J. Org. Chem. 1987; 52: 2469
• 7 Xu T, Alper H. Org. Lett. 2015; 17: 1569
• 8 Liang D, He Y, Zhu Q. Org. Lett. 2014; 16: 2748
• 9a Chen J, Feng JB, Natte K, Wu XF. Chem. Eur. J. 2015; 21: 16370
• 9b Chen J, Natte K, Wu XF. Tetrahedron Lett. 2015; 56: 6413
• 10 Chen J, Natte K, Spannenberg A, Neumann H, Langer P, Beller M, Wu XF. Angew. Chem. Int. Ed. 2014; 53: 7579
• 11 Li H, Li W, Spannenberg A, Baumann W, Neumann H, Beller M, Wu X.-F. Chem. Eur. J. 2014; 20: 8541
• 12a Yang W, Chen J, Huang X, Ding J, Liu M, Wu H. Org. Lett. 2014; 16: 5418
• 12b Yang W, Qiao R, Chen J, Huang X, Liu M, Gao W, Ding J, Wu H. J. Org. Chem. 2015; 80: 482
• 13 Gupta PK, Yadav N, Jaiswal S, Asad M, Kant R, Hajela K. Chem. Eur. J. 2015; 21: 13210
• 14 Banerji B, Bera S, Chatterjee S, Killi SK, Adhikary S. Chem. Eur. J. 2016; 22: 3506
• 15a Peng J, Chen T, Chen C, Li B. J. Org. Chem. 2011; 76: 9507
• 15b Peng J, Shang G, Chen C, Miao Z, Li B. J. Org. Chem. 2013; 78: 1242
• 15c Chen C, Shang G, Zhou J, Yu Y, Li B, Peng J. Org. Lett. 2014; 16: 1872
• 15d Zhao G, Chen C, Yue Y, Yu Y, Peng J. J. Org. Chem. 2015; 80: 2827
• 15e Wang H, Chen C, Huang Z, Yao L, Li B, Peng J. Synthesis 2015; 47: 2457
• 16a Louie J, Hartwig JF. Tetrahedron Lett. 1995; 36: 3609
• 16b Guram AS, Rennels RA, Buchwald SL. Angew. Chem. Int. Ed. 1995; 34: 1348 ; Angew. Chem. 1995, 107, 1456
• 16c Yin J, Buchwald SL. Org. Lett. 2000; 2: 1101
• 16d Yin J, Buchwald SL. J. Am. Chem. Soc. 2002; 124: 6043

Selected reviews on chelation-assisted Pd-catalyzed C–H functionalizations:
• 17a Alberico D, Scott ME, Lautens M. Chem. Rev. 2007; 107: 174
• 17b Daugulis O, Do H.-Q, Shabashov D. Acc. Chem. Res. 2009; 42: 1074
• 17c Ackermann L, Vicente R, Kapdi AR. Angew. Chem. Int. Ed. 2009; 48: 9792
• 17d Engle KM, Mei T.-S, Wasa M, Yu J.-Q. Acc. Chem. Res. 2012; 45: 788
• 17e Wu Y, Wang J, Mao F, Kwong FY. Chem. Asian J. 2014; 9: 26
• 17f Giri R, Thapa S, Kafle A. Adv. Synth. Catal. 2014; 356: 1395
• 17g Dastbaravardeh N, Christakakou M, Haider M, Schnürch M. Synthesis 2014; 46: 1421
• 18 Dupont J, Consorti CS, Spencer J. Chem. Rev. 2005; 105: 2527
• 19a Surry DS, Buchwald SL. Angew. Chem. Int. Ed. 2008; 47: 6338 ; Angew. Chem. 2008, 120, 6438
• 19b Surry DS, Buchwald SL. Chem. Sci. 2011; 2: 27
• 20 Campeau L.-C, Parisien M, Jean A, Fagnou K. J. Am. Chem. Soc. 2006; 128: 581
• 21a Guo S, Li Y, Tao L, Zhang W, Fan X. RSC Adv. 2014; 4: 59289
• 21b Abdel-Jalil RJ, Völter W, Saeed M. Tetrahedron Lett. 2004; 45: 3475