Synthesis of new heteroaromatic nitrogen ligands: Pyrimido-[4″, 5″:4′,5′]-thieno[3′,2′:4,5]thieno[3,2-d] pyrimidines and 1,2,3-triazine[4″,5″:4′,5′] thieno[3′,2′:4,5]thieno[3,2-d]-1,2,3-triazines

Journal of Heterocyclic Chemistry

Volumn 43, Issue 4, 2006, Pages 1051-1056

  Blanco, Gerardo ^a   Quintela, José M ^a   Peinador, Carlos ^a  

^a UNIVERSITY OF A CORUÑA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,3 TRIAZINE DERIVATIVE; 1,2,3 TRIAZINE[4'',5'':4',5']THIENO[3',2':4,5]THIENO[3,2 D] 1,2,3 TRIAZINE; 3,4 DIAMINOTHIENO[2,3 B]THIOPHENE 2,5 DICARBONITRILE; AROMATIC NITRO COMPOUND; HYDROCHLORIC ACID; LIGAND; NITRILE; PHOSGENE; PHOSGENIMINIUM CHLORIDE; PYRIMIDO[4'',5'':4',5']THIENO[3',2:4,5]THIENO[3,2 D]PYRIMIDINE; SODIUM NITRITE; THIENO[2,3 D]PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; INFRARED SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 33747428728     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570430435     Document Type: Article

References (59)

1. [a] N. Matzanke, R. J. Gregg, and S. M. Weinreb, Org. Prep. Proced. Int., 30, 1 (1998);
2. [b] F. Palacios, C. Alonso, P. Amezua, and G. Rubiales, J. Org. Chem., 67, 1941 (2002), and references therein;
3. [c] G. Jones, Comprehensive Heterocyclic Chemistry, ed. by A. R. Katritzky, C. W. Rees, A. J. Boulton, and A. McKillop, Pergamon, Oxford, 1984, Vol. 2;
4. (d) A. R. Renslo and R. L. Danheiser, J. Org. Chem., 63, 7840 (1998).
5. J. M. Lehn, Supramolecular Chemistry, Concepts and Perspectives, VCH, Weinheim, 1995.
6. G. Chelucci and R. P. Thummel, Chem. Rev., 102, 3129 (2002).
7. [a] A. Islam, H. Sugihara, and H. Arakawa, J. Photochem. Photobiol., 158, 131 (2003);
8. [b] M. Grätzel, Prog. Photovolt. Res. Appl., 8, 171 (2000).
9. [a] L.-N Ji, X.-H Zou, and J.-G Liu, Coord. Chem. Rev., 216-217, 513 (2001);
10. [b] D. R. McMillin and K. M. McNett, Chem. Rev., 98, 1201 (1998);
11. [c] D. S. Sigman, A. Mazumder, and D. M. Perrin, Chem. Rev., 93, 2295 (1993).
12. P. Caravan, J. J. Ellison, T. J. McMurry, and R. B. Lauffer, Chem. Rev., 99, 2293 (1999).
13. M. J. Clarke, Coord. Chem. Rev., 203, 209 (2003).
14. [a] K. Kalyanasundaram and M. Grätzel, Coord. Chem. Rev., 177, 347 (1998);
15. [b] S. M. Baxter, W. E. Jones, E. Danielson, L. Worl, G. Strouse, J. Younathan, and T. Meyer, Coord. Chem. Rev., 111, 47 (1991).
16. [a] C. V. Bird, G. W. H. Cheeseman, Eds. Comprehensive Heterocyclic Chemistry, Vol. IV, Pergamon, London, 1984, p. 1037;
17. [b] V. P. Litvinov and Y. A. L. Gol'dfarb, in Chemistry of thienothiophenes, Advanced Heterocyclic Chemistry, ed. by A. R. Katritzky and A. J. Boulton, Academic Press, New York, 1976, vol. 19, p. 123.
18. [a] P. V. Bedworth, Y. Cai, A. Jen, and S. R. Marden, J. Org. Chem., 61, 2242 (1996);
19. [b] D. M. Burland, R. D. Miller, and C. A. Walsh, Chem. Rev., 94, 31 (1994);
20. [c] K. Takahashi and M. Ogiyama, J. Chem. Soc., Chem. Commun., 1196 (1991);
21. [d] F. Garnier, Angew. Chem. Int. Ed. Engl, 28, 513 (1989).
22. D. Peters, A. B. Hörnfeldt, and S. Gronowitz, J. Heterocyclic Chem., 27, 2165 (1990).
23. S. Kukolja, S. E. Draheim, B. J. Graves, D. C. Hunden, J. L. Pfeil, R. D. G. Cooper, J. L. Ott, and F. T. Couter, J. Med. Chem., 28, 1896 (1995).
24. J. D. Prugh, G. D. Hartman, P. J. Mallorga, B. M. McKeever, S. R. Michelson, M. A. Murcko, H. Schwam, R. L. Smith, J. M. Sondey, J. P. Springer, and M. F. Surgrue, J. Med. Chem., 35, 1805 (1991).
25. J. L. Fabre, D. Farge, and C. James, German Patent 2,703,624 (1976); Chem. Abstr., 1976, 87, 168000v (1976).
26. S. Musmanni and J. P. Ferraris, J. Chem. Soc., Chem. Commun., 172 (1993).
27. D. Lorcy, K. D. Robinson, Y. Okuda, J. L. Atwood, and M. P. Cava, J. Chem. Soc., Chem. Commun., 345 (1993).
28. K. Yui, H. Ishida, Y. Aso, T. Otsubo, F. Ogura, A. Kawamoto, and J. Tanaka, Bull. Chem. Soc. Jpn., 62, 1547 (1989).
29. O. Kobayashi, Phosphorus, Sulfur, Silicon & Relat. Elem., 43, 187 (1989).
30. H. Hayata, A. Hirano, and H. Hirose, Jpn. Kokai Tokkyo Koho, JP, 1992, 043338, 761; Chem. Abstr., 118, 263832k (1992).
31. R. A. Ham and D. Bloor, Eds. Organic Materials for Nonlinear, The Royal Society of Chemistry, Cambridge, Special Publication No. 91, 1991.
32. [a] Y. A. Ibrahim, A. H. Elwahy, and A. M. Kadry, Adv. Heterocyclic Chem., 65, 235 (1996);
33. [b] G. Varvounis and T. Giannopoulos, Adv. Heterocyclic Chem., 66, 193 (1996).
34. [22a] J. M. Quintela, C. Peinador, L. M. González, R. Riguera, I. Rioja, M. C. Terencio, A. Ubeda, and M. J. Alcaraz, J. Med. Chem., 42, 4720 (1999);
35. [b] J. M. Quintela, C. Peinador, L. González, I. Devesa, M. L. Ferrándiz, M. J. Alcaraz, and R. Riguera, Bioorg. Med. Chem., 11, 863 (2003), and references therein.
36. [a] W. Ong, J. Grinstaff, D. Sobransingh, R. Toba, J. M. Quintela, C. Peinador, and A. Kaifer, J. Am. Chem. Soc., 127, 3353 (2005);
37. [b] R. Toba, J. M. Quintela, C. Peinador, E. Román, and A. Kaifer, Chem. Commun., 857 (2001);
38. [c] E. Román, M. Chas, J. M. Quintela, C. Peinador, and A. Kaifer, Tetrahedron, 58, 699 (2002);
39. [d] R. Toba, J. M. Quintela, C. Peinador, E. Román, and A. Kaifer, Chem. Commun., 1768 (2002).
40. [a] A. Khodairy, H. Abdel-Ghany, Phosphorus, Sulfur, Silicon & Relat. Elem., 162, 259 (2000);
41. [b] A. Artyomov, L. A. Rodinovskaya, A. M. Shestopalov, and V. P. Litvinov, Tetrahedron, 52, 1011 (1996);
42. [c] A. K. El-Shafei, A. M. M. El-saghier, A. Sultan, and A. M. Soliman, Phosphorus, Sulfur, Silicon & Relat. Elem., 72, 73 (1992).
43. L. M. Deck and E. P. Papadopoulos, J. Heterocyclic Chem., 37, 675 (2000) and references cited therein.
44. For a review see: Z. Janousek and H. G. Viehe, in Iminium Salts in Organic Chemistry, Advances in Organic Chemistry: Chemistry of Dichlorometileniminium Salts (Phosgeniminium Salts), ed. by H. Böhme and H. G. Viehe, John Wiley and Sons, Inc., New York, 1976, Vol. 9, p. 343.
45. For a review see: J. M. Quintela, C. Peinador, M. J. Moreira, and R. Alvarez-Sarandés, Recent. Res. Devel. In Organic Chem., 2, 409 (1998).
46. A. Comeln and G. Kirsch, J. Heterocyclic Chem., 38, 1167 (2001).
47. D. Bartholomew and I. T. Kay, Tetrahedron Lett., 2827 (1979).
48. [a] H. Kokel, J. Heterocyclic Chem., 31, 8445 (1994);
49. [b] B. Kokel, J. Heterocyclic Chem., 31, 1185 (1994);
50. [c] R. Neidlein and Zh. Wang, Synth. Commun., 27, 1223 (1997);
51. [d] J. Morris, G. P. Luke, and D. Wishka, J. Org. Chem., 61, 3218 (1996);
52. [e] C. H. M. Marsow, Tetrahedron, 48, 3659 (1992);
53. [f] J. Liebscher, Synthesis, 655 (1988).
54. W. Kantlehner, Adv. Org. Chem., 9, 65 (1979).
55. K. Hafner and H. P. Krimmer, Angew. Chem., 92, 202 (1980).
56. B. Kokel, C. Lespagnol, and H. G. Viehe, Bull. Soc. Chim. Belg., 89, 651 (1980).
57. I. Bitter, B. Pete, I. Hermecz, G. Tóth, K. Simon, M. Czugler, and Z. Mészáros, Tetrahedron Lett, 2891 (1982).
58. B. Kokel, G. Menichi, and M. Hobar-Habart, Tetrahedron Lett., 1557 (1984).
59. J. R. Beck and J. A. Yahner, J. Org. Chem., 41, 1733 (1976).