Transition-Metal-Free One-Pot Tandem Synthesis of 4-Quinolone and 4H-Thiochromen-4-one Derivatives Through Sequential Nucleophilic Addition–Elimination–S_NAr Reaction

Abstract

4-Quinolone and 4H-thiochromen-4-one derivatives are readily synthesized in a tandem one-pot manner in good to excellent yields. Starting from (Z)-β-chlorovinyl ketones, an intermolecular nucleo­philic addition of amines or sodium hydrogen sulfide to (Z)-β-chloro­vinyl ketones was followed by elimination of chlorine anion to give Z-enamine or thioenol intermediates, which can be transformed to 4-quinolone or 4H-thiochromen-4-one products through intramolecular S_NAr reaction, respectively.

Key words

quinolones - 4H-thiochromen-4-ones - nucleophilic addition - elimination - S_NAr - tandem synthesis - transition-metal-free

• References

• 1 Pozharskii AF. Soldatenkov AT. Katritzky AR. Heterocycles in Life and Society . Wiley; Chichester, UK: 1997: 135-164
• 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 BA. 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
• 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
• 17a Mehta VP. Punji B. RSC Adv. 2013; 3: 11957
• 17b Sun C.-L. Shi Z.-J. Chem. Rev. 2014; 114: 9219
• 18 March J. Advanced Organic Chemistry, Reactions, Mechanisms and Structure. 4th ed. Wiley; New York: 1992: 641
• 19 Bunnett JF. Hrutford BF. J. Am. Chem. Soc. 1961; 83: 1691
• 20a Peng J. Ye M. Zong C. Hu F. Feng L. Wang X. Wang Y. Chen C. J. Org. Chem. 2011; 76: 716
• 20b Peng J. Chen T. Chen C. Li B. J. Org. Chem. 2011; 76: 9507
• 20c Peng J. Shang G. Chen C. Miao Z. Li B. J. Org. Chem. 2013; 78: 1242
• 20d Peng J. Zhao Y. Zhou J. Ding Y. Chen C. Synthesis 2014; 46: 2051
• 20e Chen C. Shang G. Zhou J. Yu Y. Li B. Peng J. Org. Lett. 2014; 16: 1872
• 20f Zhao G. Chen C. Yue Y. Yu Y. Peng J. J. Org. Chem. 2015; 80: 2827
• 20g Wang H. Chen C. Huang Z. Yao L. Li B. Peng J. Synthesis 2015; 47: 2457
• 20h Yu Y. Yue Y. Wang D. Li X. Chen C. Peng J. Synthesis 2016; 48: 3941
• 21a Peng J. Zong C. Ye M. Chen T. Gao D. Wang Y. Chen C. Org. Biomol. Chem. 2011; 9: 1225
• 21b Chen C. Chen C. Li B. Tao J. Peng J. Molecules 2012; 17: 12506
• 22a Pohland AE. Benson WR. Chem. Rev. 1966; 66: 161
• 22b Gooßen LJ. Rodríguez N. Gooßen K. Angew. Chem. Int. Ed. 2009; 48: 9592 ; Angew. Chem. 2009, 121, 9770
• 23a Wang B. Wang S. Li P. Wang L. Chem. Commun. 2010; 46: 5891
• 23b Gandeepan P. Parthasarathy K. Su T.-H. Cheng C.-H. Adv. Synth. Catal. 2012; 354: 457
• 24 Nakazumi H. Ueyama T. Kitao T. J. Heterocycl. Chem. 1984; 21: 193
• 25 Couquelet J. Tronche P. Niviere P. Andraud G. Trav. Soc. Pharm. Montpellier 1963; 23: 214
• 26 Nakazumi H. Ueyama T. Kitao T. J. Heterocycl. Chem. 1985; 22: 1593
• 27 Holshouser MH. Loeffler LJ. Hall IH. J. Med. Chem. 1981; 24: 853
• 28a Razdan RK. Bruni RJ. Mehta AC. Weinhardt KK. Papanastassiou ZB. J. Med. Chem. 1978; 21: 643
• 28b Kumar P. Bodas MS. Tetrahedron 2001; 57: 9755
• 28c Willy B. Müller TJ. J. Synlett 2009; 1255
• 28d Fuchs FC. Eller GA. Holzer W. Molecules 2009; 14: 3814
• 28e Willy B. Frank W. Müller TJ. J. Org. Biomol. Chem. 2010; 8: 90
• 28f Kobayashi K. Kobayashi A. Ezaki K. Heterocycles 2012; 85: 1997
• 28g Li M. Cao H. Wang Y. Lv X.-L. Wen L.-R. Org. Lett. 2012; 14: 3470
• 28h Yang X. Li S. Liu H. Jiang Y. Fu H. RSC Adv. 2012; 2: 6549
• 28i Kobayashi K. Kobayashi A. Ezaki K. Heterocycles 2012; 85: 1997
• 28j Inami T. Kurahashi T. Matsubara S. Org. Lett. 2014; 16: 5660
• 28k Sangeetha S. Muthupandi P. Sekar G. Org. Lett. 2015; 17: 6006
• 28l Shen C. Spannenberg A. Wu X.-F. Angew. Chem. Int. Ed. 2016; 55: 5067
• 28m Sosnovskikh VY. Chem. Heterocycl. Compd. 2016; 52: 427
• 29 Wang X. Cheng G. Cui X. Chem. Commun. 2014; 50: 652
• 30a Shim SC. Chae SA. Lee DY. Lim HS. Kalinin VN. J. Korean Chem. Soc. 1994; 38: 774
• 30b Ding D. Li X. Wang X. Du Y. Shen J. Tetrahedron Lett. 2006; 47: 6997
• 30c Tollari S. Penoni A. Cenini S. J. Mol. Catal. A: Chem. 2000; 152: 47
• 30d Sun F. Zhao X. Shi D. Tetrahedron Lett. 2011; 52: 5633
• 30e Tang J. Huang X. Synth. Commun. 2003; 33: 3953
• 30f Genelot M. Bendjeriou A. Dufaud V. Djakovitch L. Appl. Catal., A 2009; 369: 125
• 30g Lee JI. Bull. Korean Chem. Soc. 2009; 30: 710
• 30h Lee JI. Kim MJ. Bull. Korean Chem. Soc. 2011; 32: 1383
• 30i French KL. Angel AJ. Williams AR. Hurst DR. Beam CF. J. Heterocycl. Chem. 1998; 35: 45
• 30j Truce WE. Goldhamer DL. J. Am. Chem. Soc. 1959; 81: 5795