6-endo-dig Cycloisomerization of N-Propargyl Aminoquinoxalines: A New Route to 1,4,8-Triazaphenanthrenes

This paper is dedicated in the memory of Prof Jean F. Normant, a great mentor and a wonderful person.

‡ S.V. and G.L.D. contributed equally to this work.

Abstract

We report the preparation of novel 1,4,8-triazaphenanthrenes and show that the target compounds are efficiently obtained from the corresponding 6-aminoquinoxalines after N-propargylation followed by copper-catalyzed 6-endo-dig cycloisomerization and aromatization. The cyclization was found to be completely regioselective.

Key words

copper - silver - regioselectivity - N-heterocycles - Lewis acids

• References

• 1 Legros J, Figadère B. Nat. Prod. Rep. 2015; 32: 1541
• 2a Fakhfakh MA, Franck X, Fournet A, Hocquemiller R, Figadère B. Tetrahedron Lett. 2001; 42: 3847
• 2b Quintin J, Franck X, Hocquemiller R, Figadère B. Tetrahedron Lett. 2002; 43: 3547
• 2c Fakhfakh MA, Prinat E, Mouscadet JF, Fournet A, Franck X, Hocquemiller R, Figadère B. Bioorg. Med. Chem. 2003; 11: 5013
• 2d Seck M, Franck X, Hocquemiller R, Figadère B, Peyrat JF, Provot O, Brion JD, Alami M. Tetrahedron Lett. 2004; 45: 1881
• 2e Hui X, Desrivot J, Bories C, Loiseau P, Franck X, Hocquemiller R, Figadère B. Bioorg. Med. Chem. Lett. 2006; 16: 815
• 2f Hui X, Schmidt F, Fakhfakh MA, Franck X, Hocquemiller R, Figadère B. Heterocycles 2007; 72: 353
• 2g Schmidt F, Champy P, Seon-Meniel B, Franck X, Raisman-Vozari R, Figadère B. Plos ONE 2009; 4: e6215
• 2h Schmidt F, Le Douaron G, Amar M, Seon-Meniel B, Raisman-Vozari R, Figadere B. Bioorg. Med. Chem. 2010; 18: 5103
• 2i Le Douaron G, Schmidt F, Amar M, Kadar H, Debortoli L, Latini A, Seon-Meniel B, Ferrié L, Michel PP, Touboul D, Brunelle A, Raisman-Vozari R, Figadere B. Eur. J. Med. Chem. 2015; 89: 467
• 3 Le Douaron G, Ferrié L, Sepulveda JE, Amar M, Seon-Meniel B, Raisman-Vozari R, Michel PP, Figadere B. J. Med. Chem. 2016; in press; DOI: 10.1021/acs.jmedchem.6600297
• 4a Scheurer H, Zsindely J, Schmid H. Helv. Chim. Acta 1973; 56: 478
• 4b Abbiati G, Acradi A, Bianchi G, Giuseppe SD, Marinelli F, Rossi E. J. Org. Chem. 2003; 68: 6959
• 4c Pastine SJ, Youn SW, Sames D. Org. Lett. 2003; 5: 1055
• 4d Zhang X, Yao T, Campo MA, Larock RC. Org. Lett. 2005; 7: 763
• 4e Holman MA, Williamson NW, Ward AD. Aust. J. Chem. 2005; 58: 368
• 4f Kuninobu Y, Inoue Y, Takai K. Chem. Lett. 2007; 36: 1422
• 4g Minnihan EC, Colletti SL, Toste FD, Shen HC. J. Org. Chem. 2007; 72: 6287
• 4h Godet T, Belmont P. Synlett 2008; 2513
• 4i Cacchi S, Fabrizi G, Filisti E. Org. Lett. 2008; 10: 2629
• 4j Jiang C, Xu M, Wang S, Wang H, Yao Z.-J. J. Org. Chem. 2010; 75: 4323
• 4k Zhang X, Yao T, Campo MA, Larock RC. Tetrahedron 2010; 66: 1177
• 4l Komeyama K, Igawa R, Takaki K. Chem. Commun. 2010; 46: 1748
• 4m Manzo AM, Perboni A, Broggini G, Rigamonti M. Synthesis 2011; 127
• 4n Majumdar KC, Nandi RK, Ganai S, Taher A. Synlett 2011; 116
• 4o Symeonidis TS, Kalltsakis MG, Litinas KE. Tetrahedron Lett. 2011; 52: 5452
• 4p Gurunathan S, Paramasicam TP. Tetrahedron Lett. 2011; 52: 1783
• 4q Zhu M, Fu W, Xun C, Deng D, Ji B, Zou G. J. Fluorine Chem. 2012; 135: 195
• 4r Roy B, Ansary I, Samanta S, Majumdar KC. Tetrahedron Lett. 2012; 53: 5119
• 4s Symeonidis TS, Lykakis IN, Litinas KE. Tetrahedron 2013; 69: 4612
• 4t Aichhorn S, Himmelsbach M, Schöfberger W. Org. Biomol. Chem. 2015; 13: 9373
• 5a Berger DM, Dutia MD, Demorin FF, Boschelli DH, Powell DW, Tsou H, Wissner A, Zhang N, Ye F, Wu B. PCT Int. Appl WO 2001047892, 2001
• 5b Carta A, Briguglio I, Piras S, Corona P, Boatto G, Nieddu M, Giunchedi P, Marongiu ME, Giliberti G, Iuliano F, Blois S, Ibba C, Busonera B, La Colla P. Bioorg. Med. Chem. 2011; 19: 7070
• 6a Lursker F, Evans RL. J. Am. Chem. Soc. 1946; 68: 874
• 6b Ohta A, Hasagow K, Amano K, Mori C, Ohsawa A, Ikeda K, Watanabe T. Chem. Pharm. Bull. 1979; 27: 2596
• 6c Ganguli BS, Singh B, Ferandes PS. Indian J. Heterocycl. Chem. 1994; 269
• 6d Kondo S, Shiozawa T, Terao Y. Chem. Pharm. Bull. 1997; 45: 722
• 7 Hazra CK, Oestreich M. Org. Lett. 2012; 14: 4010
• 8 Fengping X, Chen Y, Liu Y, Wang J. Tetrahedron 2008; 64: 2755
• 9 Normant JF, Bourgain M. Tetrahedron Lett. 1971; 27: 2583
• 10 Fantazier RM, Putsma ML. J. Am. Chem. Soc. 1968; 90: 5490
• 11a Kohn W, Sham L. Phys. Rev. A: At., Mol., Opt. Phys. 1965; 140: 1133
• 11b Hohenberg P, Khon W. Phys. Rev. B: Condens. Matter Mater. Phys. 1964; 136: 864
• 12a Becke AD. J. Chem. Phys. 1993; 98: 5648
• 12b Lee C, Yang W, Parr RG. Phys. Rev. B: Condens. Matter Mater. Phys. 1988; 37: 785
• 13 Hehre WJ, Radom L, Schleyer PV. R, Pople JA. Ab Initio Molecular Orbital Theory . Wiley; New York: 1986
• 14 Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA. Jr, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas Ö, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ. Gaussian 09, Revision A.02. Gaussian Inc; Wallingford CT: 2009
• 15 Chimera is developed by the Resource for Biocomputing, Visualization, and Informatics at the University of California, San Francisco (supported by NIGMS P41-GM103311).