Synthesis of pyrazinothienopyrimidine derivatives by the application of the intramolecular and intermolecular aza-wittig reaction/heterocyclization

Synthesis

Volumn , Issue 9, 2008, Pages 1397-1403

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

^a UNIVERSITY OF A CORUÑA   (Spain)

Author keywords

Azides; Cyclizations; Heterocycles; Nitrogen; Wittig reaction

Indexed keywords

CARBOXYLIC ACIDS; CYCLIZATION; DERIVATIVES; REACTION KINETICS; SYNTHESIS (CHEMICAL);

HETEROCYCLES; PYRAZINOTHIENOPYRIMIDINE DERIVATIVES; WITTIG REACTION;

PYRIDINE;

2 ETHYL 3 PHENYLYPYRAZINO[2',3':4,5]THIENO[3,2 D]PYRIMIDIN 4(3H) ONE; 2 ISOPROPYL 3 PHENYLYPYRAZINO[2',3':4,5]THIENO[3,2 D]PYRIMIDIN 4(3H) ONE; 2 METHYL 3 PHENYLYPYRAZINO[2',3':4,5]THIENO[3,2 D]PYRIMIDIN 4(3H) ONE; 2,3 DIPHENYLYPYRAZINO[2',3':4,5]THIENO[3,2 D]PYRIMIDIN 4(3H) ONE; 3 BENZYL 2 ETHYLYPYRAZINO[2',3':4,5]THIENO[3,2 D]PYRIMIDIN 4(3H) ONE; 3 BENZYL 2 ISOPROPYLYPYRAZINO[2',3':4,5]THIENO[3,2 D]PYRIMIDIN 4(3H) ONE; 3 BENZYL 2 METHYLYPYRAZINO[2',3':4,5]THIENO[3,2 D]PYRIMIDIN 4(3H) ONE; 3 BENZYL 2 PHENYLYPYRAZINO[2',3':4,5]THIENO[3,2 D]PYRIMIDIN 4(3H) ONE; ALKENE DERIVATIVE; BENZENE DERIVATIVE; BIS(PYRAZINOTHIENOPYRIMIDINYL)BENZENE DERIVATIVE; N (HETEROARYL)PHOSPHAZENE DERIVATIVE; PHOSPHAZENE DERIVATIVE; PYRAZINO[2',3':4,5]THIENO[3,2 D]PYRIMIDINE DERIVATIVE; PYRIMIDINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; MOLECULAR INTERACTION; SYNTHESIS; WITTIG REACTION;

EID: 44049106648     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1072514     Document Type: Article

References (40)

1. For recent contributions, see: (a) Cushman, M.; Sambaiah, T.; Jin, G.; Illarionov, B.; Fischer, M.; Bacher, A. J. Org. Chem. 2004, 69, 601.
2. (b) Haraguchi, K.; Kubota, Y.; Tanaka, H. J. Org. Chem. 2004, 69, 1831.
3. (c) Depecker, G.; Patino, N.; Giorgio, C. D.; Terreux, R.; Cabrol-Bass, D.; Bailly, C.; Aubertin, A.-M.; Condom, R. Org. Biomol. Chem. 2004, 2, 74.
4. For reviews on the synthesis and biological activity of thienopyridines, see: (a) Litvinov, V. P.; Dotsenko, V. V.; Krivokolysko, S. G. Russ. Chem. Bull. Int. Ed. 2005, 54, 864.
5. (b) Bakhite, E. A.-G. Phosphorus, Sulfur, Silicon Relat. Elem. 2003, 178, 929.
6. (a) Chambhare, R. V.; Khadse, B. G.; Bobde, A. S.; Bahekar, R. H. Eur. J. Med. Chem. 2003, 38, 89.
7. (b) Walter, H. WO Patent 9914202, 1999; Chem. Abstr. 1999, 130, 252368.
8. (a) Sishoo, C. J.; Shirsath, V. S.; Rathod, I. S.; Yande, V. D. Eur. J. Med. Chem. 2000, 35, 351.
9. (b) Santagati, M.; Modica, M.; Santagati, A.; Russo, F.; Spampinato, S. Pharmazie 1996, 51, 7.
10. (a) Quintela, J. M.; Peinador, C.; González, L.; Devesa, I.; Ferrándiz, M. L.; Alcaraz, M. J.; Riguera, R. Biorg. Med. Chem. 2003, 11, 863.
11. (b) Quintela, J. M.; Peinador, C.; González, L.; Iglesias, R.; Paramá, A.; Alvarez, F.; Sanmartín, M.; Riguera, R. Eur. J. Med. Chem. 2003, 38, 265.
12. (c) Rioja, I.; Ubeda, A.; Terencio, M. C.; Guillén, I.; Riguera, R.; Quintela, J. M.; Peinador, C.; González, L.; Alcaraz, M. J. Eur. J. Pharmacol. 2000, 397, 207.
13. (d) Quintela, J. M.; Peinador, C.; Gonzalez, L. M.; Rioja, I.; Terencio, M. C.; Ubeda, A.; Alcaraz, M. J.; Riguera, R. J. Med. Chem. 1999, 42, 4720.
14. (e) Quintela, J. M.; Peinador, C.; Veiga, C.; González, L.; Botana, L. M.; Alfonso, A.; Riguera, R. Bioorg. Med. Chem. 1998, 6, 1911.
15. (f) Quintela, J. M.; Peinador, C.; Veiga, M. C.; Botana, L. M.; Alfonso, A.; Riguera, R. Eur. J. Med. Chem. 1998, 33, 887.
16. (g) Peinador, C.; Ojea, V.; Quintela, J. M. J. Heterocycl. Chem. 1992, 29, 1693.
17. (a) Chill, L.; Aknin, M.; Kashman, Y. Org. Lett. 2003, 5, 2433.
18. (b) Pettit, G. R.; Tan, R.; Xu, J.; Ichihara, Y.; Williams, M. D.; Boyd, M. R. J. Nat. Prod. 1998, 61, 995.
19. (c) Immamura, N.; Nishijima, M.; Takadera, T.; Adachi, K.; Sakai, M.; Sano, H. J. Antibiot. 1997, 50, 8.
20. (a) Baker, D. C.; Hand, E. S.; Plowman, J.; Rampal, J. B.; Safavy, A.; Haugwitz, R. D.; Narayanan, V. L. Anticancer Drug Des. 1987, 2, 297.
21. (b) For a recent review, see: Pawar, V. G.; De Borggraeve, W. H. Synthesis 2006, 2799.
22. For a recent example, see: Burns, C. J.; Wilks, A. F.; Bu, X. WO Patent 2005054230, 2005; Chem. Abstr. 2005, 143, 60004.
23. For reviews, see: (a) Palacios, F.; Alonso, C.; Aparicio, D.; Rubiales, G.; de los Santos, J. M. Tetrahedron 2007, 63, 523.
24. (b) Palacios, F.; Aparicio, D.; Rubiales, G.; Alonso, C.; de los Santos, J. M. Curr. Org. Chem. 2006, 10, 2371.
25. (c) Eguchi, S. Top. Heterocycl. Chem. 2006, 6, 113.
26. (d) Eguchi, S. ARKIVOC 2005, (ii), 98.
27. (e) Arqués, A.; Molina, P. Curr. Org. Chem. 2004, 8, 827.
28. (f) Fresneda, P. M.; Molina, P. Synlett 2004, 1.
29. (a) Blanco, G.; Quintela, J. M.; Peinador, C. Tetrahedron 2007, 63, 2034.
30. (b) Blanco, G.; Seguí, N.; Quintela, J. M.; Peinador, C.; Chas, M.; Toba, R. Tetrahedron 2006, 62, 11124.
31. (c) Vázquez, D.; Peinador, C.; Quintela, J. M. Tetrahedron 2004, 60, 275.
32. (d) Álvarez-Sarandés, R.; Peinador, C.; Quintela, J. M. Tetrahedron 2001, 57, 5413.
33. Okawa, T.; Toda, M.; Eguchi, S.; Kakehi, A. Synthesis 1998, 1467.
34. Molina, P.; Conesa, C.; Velasco, M. D. Liebigs Ann./Recl. 1997, 107.
35. Wamhoff, H.; Hermann, S.; Stölben, S.; Nieger, M. Tetrahedron 1993, 49, 581.
36. Ding, M.-W.; Huang, N.-Y.; He, H.-W. Synthesis 2005, 1601.
37. Zbiral, E.; Bauer, E.; Stroh, J. Monatsh. Chem. 1971, 102, 168.
38. Lowe-Ma, C. K.; Nissan, R. A.; Wilson, W. S. J. Org. Chem. 1990, 55, 3755.
39. Crystallographic data (excluding structure factors) for 6b and 9a have been deposited with the Cambridge Crystallographic Data Center as supplementary publication numbers 6b: CCDC 668435, and 9a: CCDC 668436. Copies of the data may be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK (fax:+44 1223 33603 or e-mail: deposit@ccdc.cam.ac.uk).
40. Sheldrick, G. M. SHELXL-97 Program; University of Göttingen: Germany, 1997.