Direct transformation of Baylis-Hillman acetates into N-substituted quinolones through an SN2′→ SNAr→(Δ3,4-Δ2,3 shift)→oxidation sequence

Synthesis

Volumn , Issue 20, 2011, Pages 3379-3388

  Napoleon, John Victor ^a   Kannoth Manheri, Muraleedharan ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY MADRAS   (India)

Author keywords

antibiotics; cyclizations; photooxidations; quinolines; radical reactions

Indexed keywords

BAYLIS-HILLMAN ACETATES; CYCLIZATIONS; QUINOLINES; QUINOLONES; RADICAL REACTIONS; SENSITIZED OXIDATION; SYNTHETIC ELABORATION; THERAPEUTIC AGENTS;

ANTIBIOTICS; CYCLIZATION; PHOTOOXIDATION; REACTION KINETICS;

OXIDATION;

1 METHYL 2 PYRROLIDINONE; ACETIC ACID DERIVATIVE; ACETONITRILE; AROMATIC AMINE; BENZYLAMINE; CIPROFLOXACIN; DICHLOROETHANE; LEVOFLOXACIN; METHANOL; METHYLENE BLUE; NORFLOXACIN; OXYGEN; QUINOLINE DERIVED ANTIINFECTIVE AGENT; TETRAHYDROFURAN; TOLUENE;

ARTICLE; BAYLIS HILLMAN REACTION; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; LIGHT EXPOSURE; OXIDATION; SOLID STATE; STRUCTURE ACTIVITY RELATION; X RAY DIFFRACTION;

EID: 80053931202     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1260189     Document Type: Article

References (45)

1. Emmerson A M., Jones A M., J. Antimicrob. Chemother. 2003 51 13
2. Anderson V R., Perry C M., Drugs 2008 68 535
3. Wolfson J S., Hooper D C., Ann. Intern. Med. 1988 108 238
4. Raja A, Lebbos J, Kirkpatrick P, Nat. Rev. Drug Discovery 2004 3 733
5. Sato M, Kawakami H, Motomura T, Aramaki H, Matsuda T, Yamashita M, Ito Y, Matsuzaki Y, Yamataka K, Ikeda S, Shinkai H, J. Med. Chem. 2009 52 4869
6. Hadjeri M, Peiller E.-L, Beney C, Deka N, Lawson M A., Dumontet C, Boumendjel A, J. Med. Chem. 2004 47 4964
7. Mahmoudi N, Ciceron L, Franetich J.-F, Farhati K, Silvie O, Eling W, Sauerwein R, Danis M, Mazier D, Derouin F, Antimicrob. Agents Chemother. 2003 47 2636
8. Ito C, Itoigawa M, Furukawa A, Hirano T, Murata T, Kaneda N, Hisada Y, Okuda K, Furukawa H, J. Nat. Prod. 2004 67 1800
9. Joseph B, Darro F, Béhard A, Lesur B, Collignon F, Decaestecker C, Frydman A, Guillaumet G, Kiss R, [nl] J. Med. Chem. 2002 45 2543
10. Hopkins A L., Ren J, Milton J, Hazen R J., Chan J H., Stuart D I., Stammers D K., J. Med. Chem. 2004 47 5912
11. Boteva A A., Krasnykh O P., Chem. Heterocycl. Compd. (Engl. Transl.) 2009 45 757; and references cited therein
12. Huang J, Chen Y, King A O., Dilmeghani M, Larsen R D., Faul M M., Org. Lett. 2008 10 2609
13. Mitscher L A., Chem. Rev. 2005 105 559; and references cited therein
14. Gould R G. Jr., Jacobs W A., J. Am. Chem. Soc. 1939 61 2890
15. Bouzard D, DiCesare P, Essiz M, Jacquet J P., Remuzon P, Weber A, Oki T, Masuyoshi M, J. Med. Chem. 1989 32 537; and references cited therein
16. Hong W P., Lee K.-J, Synthesis 2006 963
17. Kim J N., Lee K Y., Kim H S., Kim T Y., Org. Lett. 2000 2 343
18. Kim J N., Lee K Y., Ham H.-S, Kim H R., Ryu E K., Bull. Korean Chem. Soc. 2001 22 135
19. Amarante G W., Benassi M, Pascoal R N., Eberlin M N., Coelho F, Tetrahedron 2010 66 4370
20. Lee K Y., Kim J M., Kim J N., Bull. Korean Chem. Soc. 2002 23 1493
21. Lee K Y., Kim J N., Bull. Korean Chem. Soc. 2002 23 939
22. Basavaiah D, Reddy R M., Kumaragurubaran N, Sharada D S., Tetrahedron 2002 58 3693
23. Felpin F.-X, Coste J, Zakri C, Fouquet E, Chem. Eur. J. 2009 15 7238
24. Pathak R, Madapa S, Batra S, Tetrahedron 2006 63 451
25. Kim K H., Lee H S., Kim J N., Tetrahedron Lett. 2009 50 1249
26. Taylor S M., Stubley-Beedham C, Stell J G. P., Biochem. J. 1984 220 67
27. Oleinick N L., Morris R L., Belichenko I, Photochem. Photobiol. Sci. 2002 1 1
28. Sissi C, Palumbo M, Curr. Med. Chem.: Anti-Cancer Agents 2003 3 439
29. Bunting J W., Fitzgerald N P., Can. J. Chem. 1985 63 655
30. 4=Bn), 6.7, and 7.7 have been deposited with the Cambridge Crystallographic Data Centre as supplementary publications CCDC 779998, CCDC 771058, and CCDC 771059, respectively; copies can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44 (1223)336033 or email: deposit@ccdc.cam.ac.uk].
31. Kim J N., Kim H S., Gong J H., Chung Y M., Tetrahedron Lett. 2001 42 8341
32. Ferroud C, Rool P, Santamaria J, Tetrahedron Lett. 1998 39 9423
33. Darmanyan A P., Lee W, Jenks W S., J. Phys. Chem. A 1999 103 2705
34. Roberts R M. G., Ostovic D, Kreevoy M M., J. Org. Chem. 1983 48 2053
35. Alberti M N., Orfanopoulos M, Chem. Eur. J. 2010 16 9414
36. Stratakis M, Orfanopoulos M, Tetrahedron 2000 56 1595
37. Fukuzumi S, Ishikawa M, Tanaka T, J. Chem. Soc., Perkin Trans. 2 1989 1037
38. Raghuvanshi R S., Singh K N., Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2008 47 1735
39. Memarian H R., Abdoli-Senejani M, Tangestaninejad S, J. Iran. Chem. Soc. 2006 3 285
40. Zerbes R, Naab P, Franckowiak G, Diehl H, US Patent 5639886 1997
41. Mokrushina G A., Kotovskaya S K., Baskakova Z M., Petrova G M., Kolmakova T V., Charushin V N., Rusinov V L., Chupakhin O N., Khim.-Farm. Zh. 1996 30 46
42. Volle J.-N, Schlosser M, Eur. J. Org. Chem. 2000 823
43. Han E.-G, Kim H J., Lee K.-J, Tetrahedron 2009 65 9616
44. ODel D K., Nicholas K M., J. Org. Chem. 2003 68 6427
45. Yoshikawa K, Kobayashi S, Nakamoto Y, Haginoya N, Komoriya S, Yoshino T, Nagata T, Mochizuki A, Watanabe K, Suzuki M, Kanno H, Ohta T, Bioorg. Med. Chem. 2009 17 8221