Novel Synthesis of 1,2-Substituted 4-Quinolones

Abstract

An efficient method for the straightforward synthesis of N-functionalized 4-quinolones and 1,2-substituted 4-quinolones from simple 2-aminoacetophenones has been developed.

Key words

2-aminoacetophenone - 4-quinolone - echinopsine

• References

• 1 Pozharskii AF, Soldatenkov AT, Katritzky AR. Heterocycles in Life and Society . Wiley; Chichester, UK: 1997: 135
• 2a Mitscher LA. Chem. Rev. 2005; 105: 559
• 2b Cheng G, Hao H, Dai M, Liu Z, Yuan Z. Eur. J. Med. Chem. 2013; 66: 555
• 3a Chen Y.-L, Fang K.-C, Sheu J.-Y, Hsu S.-L, Tzeng C.-C. J. Med. Chem. 2001; 44: 2374
• 3b Asahina Y, Iwase K, Iinuma F, Hosaka M, Ishizaki T. J. Med. Chem. 2005; 48: 3194
• 3c Odagiri T, Inagaki H, Sugimoto Y, Nagamochi M, Miyauchi RN, Kuroyanagi J, Kitamura T, Komoriya S, Takahashi H. J. Med. Chem. 2013; 56: 1974
• 4a Li L, Wang H.-K, Kuo S.-C, Wu T.-S, Mauger A, Lin CM, Hamel E, Lee K.-H. J. Med. Chem. 1994; 37: 3400
• 4b Nakamura S, Kozuka M, Bastow KF, Tokuda H, Nishino H, Suzuki M, Tatsuzaki J, Natschke SL. M, Kuo S.-C, Lee K.-H. Bioorg. Med. Chem. 2005; 13: 4396
• 4c Chang Y.-H, Hsu M.-H, Wang S.-H, Huang L.-J, Qian K, Morris-Natschke SL, Hamel E, Kuo S.-C, Lee K.-H. J. Med. Chem. 2009; 52: 4883
• 5a Cross RM, Monastyrskyi A, Mutka TS, Burrows JN, Kyle DE, Manetsch R. J. Med. Chem. 2010; 53: 7076
• 5b Cross RM, Namelikonda NK, Mutka TS, Luong L, Kyle DE, Manetsch R. J. Med. Chem. 2011; 54: 8321
• 5c Zhang Y, Clark JA, Connelly MC, Zhu F, Min J, Guiguemde WA, Pradhan A, Iyer L, Furimsky A, Gow J, Parman T, Mazouni FE, Phillips MA, Kyle DE, Mirsalis J, Guy RK. J. Med. Chem. 2012; 55: 4205
• 6 Edmont D, Rocher R, Plisson C, Chenault J. Bioorg. Med. Chem. Lett. 2000; 10: 1831
• 7 Lucero BdA, Gomes CR. B, Frugulhetti IC. de P. P, Faro LV, Alvarenga L, Souza MC. B. V, de Souza TM. L, Ferreira VF. Bioorg. Med. Chem. Lett. 2006; 16: 1010
• 8a Cecchetti V, Parolin C, Moro S, Pecere T, Filipponi E, Calistri A, Tabarrini O, Gatto B, Palumbo M, Fravolini A, Palu G. J. Med. Chem. 2000; 43: 3799
• 8b Sato M, Motomura T, Aramaki H, Matsuda T, Yamashita M, Ito Y, Kawakami H, Matsuzaki Y, Watanabe W, Yamataka K, Ikeda S, Kodama E, Matsuoka M, Shinkai H. J. Med. Chem. 2006; 49: 1506
• 8c Pasquini S, Mugnaini C, Tintori C, Botta M, Trejos A, Arvela RK, Larhed M, Witvrouw M, Michiels M, Christ F, Debyser Z, Corelli F. J. Med. Chem. 2008; 51: 5125
• 9a Reitsema RH. Chem. Rev. 1948; 43: 43
• 9b López SE, Rebollo O, Salazar J, Charris JE, Yánez C. J. Fluorine Chem. 2003; 120: 71
• 9c Boteva AA, Krasnykh OP. Chem. Heterocycl. Compd. 2009; 45: 757
• 9d Romek A, Opatz T. Eur. J. Org. Chem. 2010; 5841
• 9e Liu Q.-L, Li Q.-L, Fei X.-D, Zhu Y.-M. ACS Comb. Sci. 2011; 13: 19
• 9f Zhao J, Zhao Y, Fu H. Org. Lett. 2012; 14: 2710
• 9g Iaroshenko VO, Knepper I, Zahid M, Dudkin S, Kuzora R, Villinger A, Langer P. Org. Biomol. Chem. 2012; 10: 2955
• 9h Shao J, Huang X, Hong X, Liu B, Xu B. Synthesis 2012; 44: 1798
• 9i Victor NJ, Muraleedharan KM. Adv. Synth. Catal. 2014; 356: 3600
• 9j Ji X, Wang Z, Tan M, Huang H, Deng GJ. Asian J. Org. Chem. 2018; 7: 711
• 9k Wang D, Sun P, Jia p, Peng J, Yue Y, Chen C. Synthesis 2017; 49: 1851
• 9l Xu X, Zhang X. Org. Lett. 2017; 19: 4984
• 10 Camps R. Ber. Dtsch. Chem. Ges. 1899; 32: 3228
• 11a Li JJ. Name Reactions: A Collection of Detailed Reaction Mechanisms 2nd Ed. Springer-Verlag; Berlin: 2003: 81
• 11b Zewge D, Chen C.-Y, Deer C, Dormer PG, Hughes DL. J. Org. Chem. 2007; 72: 4276
• 12 Gould RG, Jacobs WA. J. Am. Chem. Soc. 1939; 61: 2890
• 13a Niementowski S. Ber. Dtsch. Chem. Ges. 1894; 27: 1394
• 13b Fuson RC, Burness DM. J. Am. Chem. Soc. 1946; 68: 1270
• 13c Son JK, Kim SI, Jahng Y. Heterocycles 2001; 55: 1981
• 14a Kalinin VN, Sbostakovsky MV, Ponomaryov AB. Tetrahedron Lett. 1992; 33: 373
• 14b Torii S, Okumoto H, Xu LH, Sadakane M, Shostakovsky MV, Ponomaryov AB, Kalinin VN. Tetrahedron 1993; 49: 6773
• 14c Haddad N, Tan J, Farina V. J. Org. Chem. 2006; 71: 5031
• 14d Huang J, Chen Y, King AO, Dilmeghani M, Larsen RD, Faul MM. Org. Lett. 2008; 10: 2609
• 14e Zhao T, Xu B. Org. Lett. 2010; 12: 212
• 14f Takahashi I, Morita F, Kusagaya S, Fukaya H, Kitagawa O. Tetrahedron: Asymmetry 2012; 23: 1657
• 14g Iaroshenko VO, Knepper I, Zahid M, Kuzora R, Dudkin S, Villinger A, Langer P. Org. Biomol. Chem. 2012; 10: 2955
• 14h Fei X.-D, Zhou Z, Li W, Zhu Y.-M, Shen J.-K. Eur. J. Org. Chem. 2012; 3001
• 14i Iaroshenko VO, Zahid M, Mkrtchyan S, Gevorgyan A, Altenburger K, Knepper I, Villinger A, Sosnovskikh VY, Langer P. Tetrahedron 2013; 69: 2309
• 14j Wang Y, Liang H, Chen C, Wang D, Peng J. Synthesis 2015; 47: 1851
• 15a Jones CP, Anderson KW, Buchwald SL. J. Org. Chem. 2007; 72: 7968
• 15b Bernini R, Cacchi S, Fabrizi G, Sferrazza A. Synthesis 2009; 1209
• 16 Seppänen O, Muuronen M, Helaja J. Eur. J. Org. Chem. 2014; 4044
• 17 Radl S, Dax S. Curr. Med. Chem. 1994; 1: 262
• 18a Alvarez M, Salas M, Rigat L, de Veciana A, Joule JA. J. Chem. Soc., Perkin Trans. 1 1992; 351
• 18b Bichovski P, Haas TM, Kratzert D, Streuff J. Chem. Eur. J. 2015; 21: 2339
• 18c Biswas K, Peterkin TA. N, Bryan MC, Arik L, Lehto SG, Sun H, Hsieh F.-Y, Xu C, Fremeau RT, Allen JR. J. Med. Chem. 2011; 54: 7232
• 18d Hirano J, Hamase K, Zaitsu K. Tetrahedron 2006; 62: 10065
• 18e Ji X, Li D, Wang Z, Tan M, Huang H, Deng GJ. Eur. J. Org. Chem. 2017; 6652
• 18f Li M, Li L, Gea H. Adv. Synth. Catal. 2010; 352: 2445
• 18g Markees DG, Schwab LS. Helv. Chim. Acta 1972; 55: 1319
• 18h Stanislav R, Iva O. Collect. Czech. Chem. Commun. 2014; 69: 822
• 18i Taylor NJ, Emer E, Preshlock S, Schedler M, Tredwell M, Verhoog S, Mercier J, Genicot C, Gouverneur VR. J. Am. Chem. Soc. 2017; 139: 8267
• 18j Ueno S, Shimizu R, Maeda R, Kuwano R. Synlett 2012; 23: 1639
• 19 The Merck Index . 13th ed. Merck & Co; Whitehouse Station, USA: 2001: p. 618
• 20a Price JR. Aust. J. Sci. Res., Ser. A 1949; 2: 272
• 20b Maslova MM, Marchenko NB, Polshakov VI, Glushkov RG. Khim.-Farm. Zh. 1993; 27: 57
• 20c Reuman M, Eissenstat MA, Weaver JD. Tetrahedron Lett. 1994; 35: 8303
• 21a Conrad M, Limpach L. Ber. Dtsch. Chem. Ges. 1887; 20: 944
• 21b Conrad M, Eckhardt F. Ber. Dtsch. Chem. Ges. 1889; 22: 73
• 21c Meyer H. Monatsh. Chem. 1906; 27: 255
• 22a Knorr L, Fertig E. Ber. Dtsch. Chem. Ges. 1897; 30: 937
• 22b Troeger J, Dunker E. J. Prakt. Chem. 1926; 112: 196
• 22c Troeger J, Müller W. Arch. Pharm. (Weinheim, Ger.) 1914; 252: 459
• 23 Frank J, Mészáros Z, Kömives T, Márton AF, Dutka F. J. Chem. Soc., Perkin Trans. 2 1980; 401
• 24a Dobrowolski JC, Katen A, Fraser BH, Bhadbhade M, Black DStC, Kumar N. Tetrahedron Lett. 2016; 57: 5442
• 24b Pan G.-F, Su L, Zhang Y.-L, Guo S.-H, Wang Y.-Q. RSC Adv. 2016; 6: 25375
• 25 Derabli C, Mahdjoub S, Boulcina R, Boumoud B, Merazig H, Debache A. Chem. Heterocycl. Compd. 2016; 52: 99
• 26a Xia Y, Yang Z.-Y, Xia P, Bastow KF, Tachibana Y, Kuo S.-C, Hamel E, Hackl T, Lee K.-H. J. Med. Chem. 1998; 41: 1155
• 26b Xia Y, Yang Z.-Y, Xia P, Bastow KF, Nakanishi Y, Lee K.-H. Bioorg. Med. Chem. Lett. 2000; 10: 699
• 27a Saito K, Moriya Y, Akiyama T. Org. Lett. 2015; 17: 3202
• 27b Bunce RA, Nammalwar B. J. Heterocycl. Chem. 2011; 48: 613
• 27c Wang J.-F, Liao Y.-X, Kuo P.-Y, Gau Y.-H, Yang D.-Y. Synlett 2006; 2791
• 28 Ding D, Li X, Wang X, Du Y, Shen J. Tetrahedron Lett. 2006; 47: 6997
• 29 Genelot M, Dufaud V, Djakovitch L. Tetrahedron 2011; 67: 976
• 30a Coppola GM. J. Heterocycl. Chem. 1982; 19: 727
• 30b Yoshino Y, Kurahashi T, Matsubara S. J. Am. Chem. Soc. 2009; 131: 7494
• 31 Tambe YB, Somesh S, Arunendra P, Reddy LR. Synth. Commun. 2012; 42: 1341
• 32 Mehra MK, Mukund PT, Arun V, Kumar I, Dalip K. Org. Biomol. Chem. 2017; 15: 4956
• 33 Arava VR, Bandatmakuru SR. Synthesis 2013; 45: 1039
• 34 Audisio D, Messaoudi S, Peyrat J.-FO, Brion J.-D, Alami M. J. Org. Chem. 2011; 76: 4995
• 35 Carr RM, Sutherland DR. J. Labelled Compd. Radiopharm. 1994; 34: 961
• 36a Almeida AI. S, Silva AM. S, Cavaleiro JA. S. Synlett 2010; 462
• 36b Cross RM, Monastyrskyi A, Mutka TS, Burrows JN, Kyle DE, Manetsch R. J. Med. Chem. 2010; 53: 7076
• 37 Venkataraman S, Barange DK, Pal M. Tetrahedron Lett. 2006; 47: 7317
• 38a Zhao T, Xu B. Org. Lett. 2010; 12: 212
• 38b Hessian KO, Flynn BL. Org. Lett. 2005; 8: 243
• 38c Cross RM, Manetsch R. J. Org. Chem. 2010; 75: 8654