Rapid microwave-assisted solution phase synthesis of substituted 2-pyridone libraries

Tetrahedron

Volumn 60, Issue 39, 2004, Pages 8633-8644

  Gorobets, Nikolay Yu ^a   Yousefi, Behrooz H ^a   Belaj, Ferdinand ^a   Kappe, C Oliver ^a  

^a UNIVERSITY OF GRAZ   (Austria)

Author keywords

2 Pyridones; 2 Quinolones; Microwave synthesis; Multi component reactions

Indexed keywords

2,2 DIMETHYL 4 OXO 1,2,3,4 TETRAHYDROBENZO[4,5]IMIDAZO[1,2 A]QUINOLIN 6 YLCYANIDE; 2,5 DIOXO 1,2,5,6,7,8 HEXAHYDRO 3 QUINOLINE CARBOXAMIDE; 7,7 DIMETHYL 2,5 DIOXO 1,2,5,6,7,8 HEXAHYDRO 3 QUINOLINECARBONITRILE; 7,7 DIMETHYL 2,5 DIOXO 1,2,5,6,7,8 HEXAHYDRO 3 QUINOLINECARBOXAMIDE; DIMETHYLAMMONIUM 2 (2 CARBAMOYL 2 CYANO 1 ETHENYL) 5,5 DIMETHYL 3 OXO 1 CYCLOHEXEN 1 OLATE; DIMETHYLAMMONIUM 2 (2,2 DICYANOVINYL) 5,5 DIMETHYL 3 OXO 1 CYCLOHEXEN 1 OLATE; DIMETHYLAMMONIUM 3 CYANO 7,7 DIMETHYL 5 OXO 1,2,5,6,7,8 HEXAHYDRO 2 QUINOLIN 4 OLATE; METHYL 3 (4 METHOXYPHENYLCARBAMOYL) 6 METHYL 2 OXO 1,2 DIHYDRO 5 PYRIDINECARBOXYLATE; METHYL 7,7 DIMETHYL 2,5 DIOXO 1,2,5,6,7,8 HEXAHYDRO 3 QUINOLINECARBOXYLATE; N (4 METHOXYPHENYL) 1,3 DIMETHYL 2,4,7 TRIOXO 1,2,3,4,7,8 HEXAHYDROPYRIDO[2,3 D]PYRIMIDINE 6 CARBOXAMIDE; N 1 (4 METHOXYPHENYL) 2 CYANO 3 DIMETHYLAMINO 2 PROPENAMIDE; N 3 (2 PYRIDYL) 2,5 DIOXO 1,2,5,6,7,8 HEXAHYDRO 3 QUINOLINECARBOXAMIDE; N 3 (2 PYRIDYL) 7,7 DIMETHYL 2,5 DIOXO 1,2,5,6,7,8 HEXAHYDRO 3 QUINOLINECARBOXAMIDE; N 3 (4 FLUOROPHENYL) 7,7 DIMETHYL 2,5 DIOXO 1,2,4A,5,6,7,8,8A OCTAHYDRO 3 QUINOLINECARBOXAMIDE; N 3 (4 METHOXYPHENYL) 2 IMINOCOUMARIN 3 CARBOXAMIDE; N 3 (4 METHOXYPHENYL) 2,5 DIOXO 2H,5H PYRANO[3,2 C]CHROMENE 3 CARBOXAMIDE; N 3 (4 METHOXYPHENYL) 5 ACETYL 6 METHYL 2 OXO 1,2 DIHYDRO 3 PYRIDINECARBOXAMIDE; N 3 (4 METHOXYPHENYL) 6 METHYL 2,5 DIOXO 1,2,5,6 TETRAHYDROBENZO[H][1,6] NAPHTHYRIDINE 3 CARBOXAMIDE; N 3 (4 METHOXYPHENYL) 6 METHYL 2,5 DIOXO 5,6 DIHYDRO 2H PYRANO[3,2 C]QUINOLINE 3 CARBOXAMIDE; N 3 (4 METHOXYPHENYL) 7,7 DIMETHYL 2,5 DIOXO 1,2,5,6,7,8 HEXAHYDRO 3 QUINOLINECARBOXAMIDE; N 3 BENZYL 7,7 DIMETHYL 2,5 DIOXO 1,2,5,6,7,8 HEXAHYDRO 3 QUINOLINECARBOXAMIDE; N 3 PHENYL 2,5 DIOXO 1,2,5,6,7,8 HEXAHYDRO 3 QUINOLINECARBOXAMIDE; N 3 PHENYL 7,7 DIMETHYL 2,5 DIOXO 1,2,5,6,7,8 HEXAHYDRO 3 QUINOLINECARBOXAMIDE; N 3 PROPYL 2,5 DIOXO 1,2,5,6,7,8 HEXAHYDRO 3 QUINOLINECARBOXAMIDE; N 3 PROPYL 7,7 DIMETHYL 2,5 DIOXO 1,2,5,6,7,8 HEXAHYDRO 3 QUINOLINECARBOXAMIDE; N 6 (4 METHOXYPHENYL) 1,3 DIMETHYL 2,4,7 TRIOXO 1,3,4,7 TETRAHYDRO 2H PYRANO[2,3 D]PYRIMIDINE 6 CARBOXAMIDE; PIPERIDINIUM 3 [2 CYANO 2 (4 METHOXYPHENYLCARBAMOYL)ETHENYL] 2 OXO 2H CHROMEN 4 OLATE; PIPERIDINIUM 5 [2 CYANO 2 (4 METHOXYPHENYLCARBAMOYL) 1 ETHENYL] 1,3 DIMETHYL 2,4 BARBITURATE; PYRIDONE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; CHEMICAL REACTION KINETICS; DRUG SYNTHESIS; MICROWAVE RADIATION; POLYMERIZATION; PRIORITY JOURNAL; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

EID: 4344680844     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.05.100     Document Type: Article

References (53)

1. For a review see: Rigby J.H. Synlett. 2000;1-12
2. For a review see: Kappe T. Farmaco. 54:1999;309-315
3. Bar G., Parsons A., Thomas C.B. Tetrahedron Lett. 41:2000;7751-7755
4. Lee Y.R., Kweon H.I., Koh W.S., Min K.R., Kim Y., Lee S.H. Synthesis. 2001;1851-1855
5. De Clercq E. Farmaco. 54:1999;26-45
6. Parreira R.L.T., Abrahao O., Galembeck S.E. Tetrahedron. 57:2001;3243-3253
7. Pastelin G., Mendez R., Kabela E., Farah A. Life Sci. 33:1983;1787-1796
8. Presti E.L., Boggia R., Feltrin A., Menozzi G., Dorigo P., Mosti L. Farmaco. 54:1999;465-474
9. Dorigo P., Fraccarolo D., Gaion R.M., Santostasi G., Borea P.A., Floreani M., Mosti L., Maragno I. Gen. Pharm. 28:1997;781-788
10. Altomare C., Cellamare S., Summo L., Fossa P., Mosti L., Carotti A. Bioorg. Med. Chem. 8:2000;909-916
11. Anderson W.K., Dean D.C., Endo T. J. Med. Chem. 33:1990;1667-1675
12. Margolin, S. B. US Patent 5,962,478, 1999.
13. For a review see: Li Q., Mitscher L.A., Shen L.L. Med. Res. Rev. 20:2000;231-293
14. Dragovich P.S., Prins T.J., Zhou R., Brown E.L., Maldonado F.C., Fuhrman S.A., Zalman L.S., Tuntland T., Lee C.A., Patick A.K., Matthews D.A., Hendrickson T.F., Kosa M.B., Liu B., Batugo M.R., Gleeson J.-P.R., Sakata S.K., Chen L., Guzman M.C., Meador J.W. III, Ferre R.A., Worland S.T. J. Med. Chem. 45:2002;1607-1623
15. Dragovich P.S., Prins T.J., Zhou R., Johnson T.O., Brown E.L., Maldonado F.C., Fuhrman S.A., Zalman L.S., Patick A.K., Matthews D.A., Hou X., Meador J.W., Ferre R.A., Worland S.T. Bioorg. Med. Chem. Lett. 12:2002;733-738
16. Patankar S.J., Jurs P.C. J. Chem. Inf. Comput. Sci. 42:2002;1053-1068
17. Rougeot E., Moskowitz H., Miocque M. J. Heterocycl. Chem. 20:1983;1407-1409
18. Higashino T., Goto A., Miyashita A., Hayashi E. Chem. Pharm. Bull. 34:1986;4352-4355
19. Schurreit T. Arch. Pharm. 320:1987;500-506
20. Heber D. Arch. Pharm. 320:1987;445-450
21. Nohara A., Ishiguro T., Sanno Y. Tetrahedron Lett. 13:1974;1183-1186
22. Ukawa K., Ishiguro T., Wada Y., Nohara A. Heterocycles. 24:1986;1931-1941
23. Gibson K.R., Hitzel L., Mortishire-Smith R.J., Gerhard U., Jelley R.A., Reeve A.J., Rowley M., Nadin A., Owens A.P. J. Org. Chem. 67:2002;9354-9360
24. Collins I., Moyes C., Davey W.B., Rowley M., Bromidge F.A., Quirk K., Atack J.R., McKernan R.M., Thompson S.-A., Wafford K., Dawson G.R., Pike A., Sohal B., Tsou N.N., Ball R.G., Castro J.L. J. Med. Chem. 45:2002;1887-1900
25. Abu-Shanab F.A., Redhouse A.D., Thompson J.R., Wakefield B.J. Synthesis. 1995;557-560
26. Jones W.D.J., Schnettler R.A., Huber E.W. J. Heterocycl. Chem. 27:1990;511-518
27. Fukatsu H., Kato Y., Murase S., Nakagawa S. Heterocycles. 29:1989;1517-1528
28. Sircar I., Duell B.L., Bristol J.A., Weishaar R.E., Evans D.B. J. Med. Chem. 30:1987;1023-1029
29. Robertson D.W., Beedle E.E., Swartzendruber J.K., Jones N.D., Elzey T.K., Kauffman R.F., Wilson H., Hayes J.S. J. Med. Chem. 29:1986;635-640
30. Mosti L., Schenone P., Menozzi G. J. Heterocycl. Chem. 22:1985;1503-1509
31. Singh B. Heterocycles. 23:1985;1479-1482
32. Zacharias G., Wolfbeis O.S., Junek H. Monatsh. Chem. 105:1974;1283-1291
33. Fossa P., Boggia R., Presti E.L., Mosti L., Dorigo P., Floreani M. Farmaco. 52:1997;523-530
34. Junek H., Wolfbeis O.S., Sprintschnik H., Wolny H. Monatsh. Chem. 108:1977;689-702
35. For general references on microwave chemistry, see: (a) Loupy A. Microwaves in Organic Synthesis. 2002;Wiley, Weinheim
36. Hayes B.L. Microwave Synthesis: Chemistry at the Speed of Light. 2002;CEM, Matthews, NC
37. Lidstöm P., Tierney J.P. Microwave-Assisted Organic Synthesis. 2004;Blackwell, Oxford, (d) For online resources and a literature database on microwave-assisted organic synthesis, see: http://www.maos.net
38. For recent examples of the use of DMFDMA in microwave-assisted heterocyclic synthesis, see: (a) Westman J., Lundin R., Stalberg J., Ostbye M., Franzen A., Hurynowicz A. Comb. Chem. High Throughput Screening. 5:2002;565-570
39. Giacommelli G., Porcheddu A., Salaris M., Taddei M. Eur. J. Org. Chem. 2003;537-541. See also Ref. 40
40. Ried W., Schleimer B. Angew. Chem. 70:1958;164
41. Kovalenko S.M., Bylov I.E., Sytnik K.M., Chernykh V.P., Bilokin Y.V. Molecules. 5:2000;1146-1165
42. Brzozowski Z., Saczewski F. Eur. J. Med. Chem. 37:2002;709-720
43. Molteni V., Hamilton M.M., Mao L., Crane C.M., Termin A.P., Wilson D.M. Synthesis. 2002;1669-1674
44. Bogdal D. J. Chem. Res., S. 1998;468-469
45. Ramani A., Chanda B.M., Velu S., Sivasanker S. Green Chem. 1:1999;163-165
46. (a) Unit cell parameters: a 9.079(4) b 9.371(5) c 10.353(4), alpha 94.74(3) beta 113.43(4) gamma 112.70(4), space group P-1. (b) Crystallographic data (excluding structure factors) for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 219855 Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK (fax:+44-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk)
47. Stadler A., Kappe C.O. J. Comb. Chem. 3:2001;624-630
48. Shukla S., Bhatia P. J. Ind. Chem. Soc. 55:1978;281-283
49. Dorokhov V.A., Baranin S.V., Stashina G.A., Zhulin V.M. Izv. Akad. Nauk SSSR, Ser. Khim. 1989;211-212
50. Dorokhov V.A., Baranin S.V., Dib A., Bogdanov V.S., Yakovlev I.P., Stashina G.A., Zhulin V.M. Izv. Akad. Nauk SSSR, Ser. Khim. 1990;2107-2113
51. Mosti L., Schenone P., Menozzi G. J. Heterocycl. Chem. 22:1985;1503-1509
52. Pakhurova T.F., Paulins J., Gudriniece E., Dashkevich S., Ablovatskaya M.V. Khim. Geterotsikl. Soedin. 1982;1562-1563
53. Gotthardt H., Hoffmann N. Liebigs Ann. Chem. 1985;901-912