Synthesis of π-conjugated thiophenes starting from substituted 3-oxopropanenitriles via Gewald reaction

Tetrahedron

Volumn 64, Issue 49, 2008, Pages 11262-11269

  Puterová, Zita ^a,b   Andicsová, Anita ^a   Végh, Daniel ^a  

^a SLOVAK UNIVERSITY OF TECHNOLOGY   (Slovakia)

^b Faculty of Natural Sciences   (Slovakia)

Author keywords

[No Author keywords available]

Indexed keywords

2 ((9H FLUOREN 9 YLIDENE)METHYL) 1 METHYL 1H PYRROLE; 3 (1 METHYL 1H PYRROL 2 YL) 3 OXOPROPANENITRILE; 3 OXO 3 (THIOPHEN 2 YL)PROPANENITRILE; 3 OXO 3 PHENYLPROPANENITRILE; 5 AMINO 3 (THIOPHEN 2 YL)THIOPHENE 2,4 DICARBONITRILE; METHYL 2 AMINO 5 CYANO 4 (1 METHYL 1H PYRROL 2 YL) THIOPHENE 3 CARBOXYLATE; METHYL 2 AMINO 5 CYANO 4 (5 (9H FLUOREN 9 YLIDENE) METHYLPYRROL 2 YL)THIOPHEN 3 CARBOXYLATE; METHYL 2 AMINO 5 CYANO 4 (THIOPHENE 2 YL)THIOPHENE 3 CARBOXYLATE; METHYL 2 AMINO 5 CYANO 4 PHENYLTHIOPHENE 3 CARBOXYLATE; METHYL 2 AMINO 5 METHYL 4 [3' METHOXYCARBONYL 5' CYANO 4' (THIOPHEN 2'' YL)THIOPHEN] 3 CARBOXYLATE; METHYL 5 CYANO 2 PROPIONYL 4 (THIOPHEN 2 YL)THIOPHEN 3 CARBOXYLATE; METHYL 5 CYANO 4 (THIOPHEN 2 YL)THIOPHENE 3 CARBOXYLATE; NITRILE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; DIMERIZATION; GEWALD REACTION; POLYMERIZATION; PRIORITY JOURNAL; SULFONATION; SYNTHESIS;

EID: 54549084268     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.09.032     Document Type: Article

References (63)

1. For recent syntheses of various derivatives from substituted 3-oxopropanenitriles, see:
2. Magnus N.A., Staszak M.A., Udodong U.E., and Wepsiec J.P. Org. Process Res. Dev. 10 (2006) 899
3. Alias S., Andreu R., Blesa M.J., Franco S., Garin J., Gragera A., Orduna J., Romero P., Villacampa B., and Allain J. J. Org. Chem. 72 (2007) 6440
4. Hughes T.V., Emanuel S.L., Beck A.K., Wetter S.K., Connolly P.J., Karnachi P., Reuman M., Seraj S., Fuentes-Pesquera A.R., Gruninger R.H., Middleton S.A., Lin R., Davis J.M., and Moffat D.F.C. Bioorg. Med. Chem. 17 (2007) 3266
5. Zhu D., Ankati H., Mukherjee Ch., Yang Y., Biehl E.R., and Hua L. Org. Lett. 9 (2007) 2561
6. Ryabukhin S.V., Plaskon A.S., Ostapchuk E.N., Volochnyuk D.M., Shishkin O.V., Shivanyuk A.N., and Tolmachev A.A. Org. Lett. 9 (2007) 4215
7. Burgaz E.V., Yilmaz M., Pekel A.T., and Öktemer A. Tetrahedron 63 (2007) 7229
8. Kubač D., Kaplan O., Elišáková V., Pátek M., Vojtech V., Slámová K., Tóthová A., Lemaire M., Gallienne E., Lutz-Wahl S., Fischer L., Kuzma M., Pelantová H., van Pelt S., Bolte J., Křen V., and Martinková L. J. Mol. Catal. B: Enzym. 50 (2008) 107
9. Fleming F.F., and Iyer P.S. Synthesis (2006) 893
10. Shirakawa H., Louis E.J., MacDiarnid A.G., Chiang C.K., and Heeger A.J. J. Chem. Soc., Chem. Commun. (1977) 578
11. Shirakawa H. Synth. Met. 125 (2002) 3
12. MacDiarmid A.G. Synth. Met. 125 (2002) 11
13. Heeger A.J. Synth. Met. 125 (2002) 23
14. Application of oligothiophenes and other π-conjugated organic oligomers is outlined in:
15. Hoeben F.J.M., Jonkheijm P., Meijer E.W., and Schenning A.P.H.J. Chem. Rev. 105 (2005) 1491
16. Constanzo F., Tonelli D., Scalmani G., and Cornil J. Polymer 47 (2006) 6692
17. Sonar P., Benmansour H., Geiger T., and Schlüter A.D. Polymer 48 (2007) 4996
18. Schueppel R., Schmidt K., Ulrich C., Schulze K., Wynands D., Brédas J.L., Brier E., Reinold E., Bu H.B., Bauerle P., Maenning B., Pfeiffer M., and Leo K. Phys. Rev. B 77 (2008) 08531
19. Recent publications on sophisticated synthesis of oligothiophenes with predicted structure with an use in opto-electronics:
20. Otsubo T., Aso Y., Takimyja A., Nakanishi H., and Sumi N. Synth. Met. 133-134 (2003) 325
21. Didier D., Sergeyev S., and Geerts Y.H. Tetrahedron 63 (2007) 941
22. Zrig S., Rémy P., Andrioletti B., Rose E., Asselberghs I., and Clays K. J. Org. Chem. 73 (2008) 1563
23. Aldakov D., Querner C., Kervella Y., Jousselme B., Demadrille R., Rossito E., Reiss P., and Pron A. Microchim. Acta 160 (2008) 335
24. Cornelis D., Peeters H., Zrig S., Andrioletti B., Rose E., Verbiest T., and Koeckelbierghs G. Chem. Mater. 20 (2008) 2133
25. Studies of an influence of substitution and chain length of oligothiophenes to opto-electronical properties:
26. Torsi L., Dodabalapur A., Rothberg L.J., Fung A.W., and Katz H.E. Science 272 (1996) 1462
27. Čík G., Zálupský P., Cirák J., Tomčík P., and Végh D. Synth. Met. 139 (2003) 355
28. The use of the Gewald reaction and its modifications on synthesis of various organic compounds reported here:
29. Sabnis R.W., Rangnekar D.W., and Sonawane N.D. J. Heterocycl. Chem. 36 (1999) 333
30. Gewald K. Angew. Chem. 73 (1961) 114
31. Gronowitz S., and Fortea-Laguna J. Acta Pharm. Suecica 5 (1968) 563
32. Adachi I., Yamamori T., Hiramatsu Y., Sakai K., Mihara S.I., Kawakami M., Masui M., Uno O., and Ueda M. Chem. Pharm. Bull. 36 (1988) 4389
33. Naumann B., Böhm R., Fülöp F., and Bernáth G. Pharmazie 51 (1991) 4
34. Gütschow M., and Neumann U. J. Med. Chem. 41 (1998) 5437
35. Castanedo G.M., and Sutherlin D.P. Tetrahedron Lett. 42 (2001) 7181
36. Lütjens H., Zickraf A., Figler J., Ollsson R.A., and Scammels P.J. J. Med. Chem. 46 (2003) 1870
37. Linag Fu T., and Jing Wang I. Dyes Pigments 76 (2008) 590
38. For deaminations on substituted 2-aminothiophenes see:
39. Mitchell R., and Iyer V.S. J. Am. Chem. Soc. 118 (1996) 772
40. Švedov V.I., Rižkova V.K., and Grinev A.N. Khim. Get. Soed. 6 (1967) 1010
41. Hallas G., and Choi J.H. Dyes Pigments 40 (1999) 99
42. Yen M.S., and Wang I.J. Dyes Pigments 67 (2005) 183
43. Christie R.M., and Freer B.G. Dyes Pigments 33 (1997) 107
44. Hawskey D., Griffin D.A., and Leeper F.J. J. Chem. Soc., Perkin Trans. 1 (2001) 144
45. Drauz, K.; Kleeman, A.; Wolf-Heuss, E. U.S. Patent 4,716,237, December 1987.
46. Polívka Z., Holubek J., Metyš J., and Protiva M. Collect. Czech. Chem. Commun. 49 (1984) 621
47. Ji Y., Trenkle W.C., and Wovles J.W. Org. Lett. 8 (2006) 1161
48. Slätt J., Romero I., and Bergman J. Synthesis 16 (2004) 2760
49. Elnagdi M.H., Elmoghayar M.R.H., and Elgemeie E.H. Synthesis (1984) 1
50. Charas A., Morgado J., Martinho J.M.G., Alcacer R., Lim S.F., Friend L.H., and Cacialli F. Polymer 44 (2003) 1843
51. Lukeš V., Matis M., Végh D., Štefko M., Hrdlovič P., and Laurinc V. Synth. Met. 148 (2005) 179
52. Lukeš V., Végh D., Hrdlovič P., Štefko M., Matuszna K., and Laurinc V. Synth. Met. 157 (2007) 770
53. Perašínová L., Štefko M., Végh D., and Kožíšek J. Acta Crystallogr. E64 (2008) o274
54. Fujita M., Hirayama T., and Ikeda T. Bioorg. Med. Chem. 10 (2002) 3113
55. Gütschow M., Kuerschner L., Neumann U., Pietsch M., Löser R., Koglin N., and Eger K. J. Med. Chem. 42 (1999) 5437
56. Pietsch M., and Gütschow M. J. Med. Chem. 48 (2005) 8270
57. Gudrieniece E.Yu., Pālītis E.L., and Barkāne V.P. Izv. Akad. Nauk. Latv. SSR 614 (1983) 563
58. Litvinov V.P. Russ. Chem. Rev. 68 (1999) 39
59. Cohen, M. P.; D'Sidocky, R. M. U.S. Patent 4,873,291, October 1989.
60. Barnes D.M., Haight A.R., Hameury T., McLaughlin M.A., Mei J., Tedrow J.S., and Riva Toma J.D. Tetrahedron 62 (2006) 11311
61. Puterová Z., Végh D., Gottasová R., and Végh Z. ARKIVOC XII (2005) 36
62. Ottoni O., de Neder A.V.F., Dias A.K.B., Cruz R.P.A., and Aquino L.B. Org. Lett. 3 (2001) 1005
63. Gazit A., Osherov N., Posner I., Yaish P., Poradosu E., Gilon Ch., and Levitzki A. J. Med. Chem. 34 (1991) 1896