Novel regioselective preparation of 5-chloropyrazine-2-carbonitrile from pyrazine-2-carboxamide and coupling study of substituted phenyl-sulfanylpyrazine-2-carboxylic acid derivatives

Current Organic Chemistry

Volumn 9, Issue 1, 2005, Pages 49-60

  Jampílek, Josef ^a   Doležal, Martin ^a,c   Kuneš, Jiří ^a   Šatínský, Dalibor ^a   Raich, Ivan ^b  

^a Charles University in Prague Faculty of Pharmacy   (Czech Republic)

^b INSTITUTE OF CHEMICAL TECHNOLOGY   (Czech Republic)

^c Dept Pharmaceut Chem/Drug Control ^*  (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACIDS; CATALYSTS;

BENZENETHIOLS; CARBONITRILES; CARBOXAMIDES; CARBOXYLIC ACID DERIVATIVES; CHLOROPYRAZINE; COPPER CATALYST; IONIC MECHANISMS; PYRAZINES; REGIO-SELECTIVE; REGIOSELECTIVE PREPARATION;

REGIOSELECTIVITY;

3 [(3 METHOXYPHENYL)SULFANYL]PYRAZINE 2 CARBONITRILE; 3 [(3 METHOXYPHENYL)SULFANYL]PYRAZINE 2 CARBOXAMIDE; 3 [(3 METHOXYPHENYL)SULFANYL]PYRAZINE 2 CARBOXYLIC ACID; 3 [(4 METHOXYPHENYL)SULFANYL]PYRAZINE 2 CARBONITRILE; 3 [(4 METHOXYPHENYL)SULFANYL]PYRAZINE 2 CARBOXAMIDE; 5 CHLOROPYRAZINE 2 CARBONITRILE; 5 [(3 METHOXYPHENYL)SULFANYL]PYRAZINE 2 CARBONITRILE; 5 [(3 METHOXYPHENYL)SULFANYL]PYRAZINE 2 CARBOXAMIDE; 5 [(4 METHOXYPHENYL)SULFANYL]PYRAZINE 2 CARBONITRILE; 5 [(4 METHOXYPHENYL)SULFANYL]PYRAZINE 2 CARBOXAMIDE; 6 (PHENYLSULFANYL)PYRAZINE 2 CARBONITRILE; 6 [(3 METHOXYPHENYL)SULFANYL]PYRAZINE 2 CARBONITRILE; 6 [(3 METHOXYPHENYL)SULFANYL]PYRAZINE 2 CARBOXAMIDE; 6 [(3 METHOXYPHENYL)SULFANYL]PYRAZINE 2 CARBOXYLIC ACID; 6 [(4 METHOXYPHENYL)SULFANYL]PYRAZINE 2 CARBONITRILE; 6 [(4 METHOXYPHENYL)SULFANYL]PYRAZINE 2 CARBOXAMIDE; 6 [(4 METHOXYPHENYL)SULFANYL]PYRAZINE 2 CARBOXYLIC ACID; ANTIFUNGAL AGENT; CARBON; CARBOXYLIC ACID DERIVATIVE; COPPER; ETHYL 6 [(3 METHOXYPHENYL)SULFANYL]PYRAZINE 2 CARBOXYLATE; ION; METHYL 6 METHOXYPYRAZINE 2 CARBOXYLATE; PYRAZINAMIDE; PYRAZINE; PYRAZINE DERIVATIVE; RADICAL; THIOPHENOL DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

BINDING AFFINITY; CALCULATION; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHEMICAL ANALYSIS; CHEMICAL PROCEDURES; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CONTROLLED STUDY; CORRELATION ANALYSIS; DRUG SYNTHESIS; ELECTRON; PROTON NUCLEAR MAGNETIC RESONANCE; REVIEW; SUBSTITUTION REACTION;

EID: 11444263258     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/1385272053369312     Document Type: Review

References (41)

1. Nováček, L.; Palát, K.;Čeladník, M. Chem. Listy, 1963, 57, 299.
2. Foks, H. Acta Pol. Pharm., 1976, 33, 153.
3. Nováček, L.; Palát, K.; Čeladník, M.; Kubala, E. Cesk. Farm., 1972, 21, 145.
4. Nováček, L.; Palát, K.;Čeladník, M.; Holik, M. Coll. Czech. Chem. Commun., 1972, 37, 862.
5. Asai, M. Yakugaku Zasshi, 1961, 81, 1475.
6. Palamidessi, G.; Vigevani, A.; Zarini, F. J. Heterocycl. Chem., 1974, 11, 607.
7. Klein, B.; Hetman, N.E.; O'Donnell, M.E. J. Org. Chem., 1963, 28, 1682.
8. Okada, S.; Kosasayama, A.; Konno, T.; Uchimaru, F. Chem. Pharm. Bull., 1971, 19, 1344.
9. Klein, B.; Berkowitz, J. J. Amer. Chem. Soc., 1959 81, 160.
10. O Ochiai, K. Chem. Pharm. Bull., 1960, 8, 33.
11. Foks, H. Acta Pol. Pharm., 1976, 33, 153.
12. Foks, H.; Sawlewicz, J. Acta Pol. Pharm., 1964, 21, 458.
13. Foks, H.; Sawlewicz, J. Acta Pol. Pharm., 1966, 23, 437.
14. Doležal, M. Ph.D. Thesis. Charles University, Prague 1996.
15. Jampílek, J. Ph.D. Thesis. Charles University, Prague 2004.
16. Palmer, M.H. In The Structure and Reactions of Heterocyclic Compounds; Edward Arnold Publisher Ltd.: London, 1967 pp. 89-92.
17. Sato, N. J. Chem. Res. Miniprint, 1984, 10, 2860.
18. Zhang, Y.; Wade, M.M.; Scorpio, A.; Zhang, H.; Sun, Z. J. Antimicrob. Chemother., 2003, 52, 790.
19. Doležal, M.; Bajerová, J.; Buchta, V. In Proc. Liblice 2001 Conf., November 19-21 2001, Nymburk, Czech Republic, Chem. Listy, 2001, 95, 748.
20. Krinková, J.; Doležal, M.; Hartl, J.; Buchta, V.; Pour, M. Farmaco, 2002, 57, 71.
21. Jampílek, J.; Doležal, M.; Raich, I.; Liška, F. In Proc. ESOR-9 Conf, July 12-17, 2003, Oslo, Norway, pp. 169.
22. Jampílek, J.; Doležal, M.; Kuneš, J.; Víchová, P.; Jun, D.; Raich, I.; O'Connor, R.; Clynes, M. Curr. Org. Chem., 2004, 8, 1235.
23. Bernardi, L.; Palamidessi, G.; Leone, A.; Larini, G. Gaz. Chim. Ital., 1961, 91, 1431.
24. Kushner, S.; Williams, J.H. J. Amer. Chem. Soc., 1952, 74, 3617.
25. Foks, H.; Janowiec, M.; Zieleniecki, M. Pol. J. Pharmacol. Pharm., 1977, 29, 663.
26. Ricci, D.; Maggiali, C.A.; Ronchini, F.; Tirillini, B.; Fraternale, D. Phytochemistry, 1991, 30, 2821.
27. Albert, D.R. J. Chem. Soc., 1956, 2066.
28. Jampílek, J.; Doležal, M.; Deigner, H.P. Folia Pharm. Univ. Carol., 2002, 27/28, 69. http://www.fafcuni.cz/folia/27/2709jampilek.htm.
29. Abe, Y.; Shigeta, Y.; Uchimaru, F. Japan 1969, 69/12/898.
30. Jampílek, J.; Doležal, M.; Dvo řák, B. In Proc. ECSOC-6 Conf., September 1-30, 2002, S.K. Lin, J.A. Seijas Ed.; CD-ROM edition, MDPI, Basel, 2002, http://www.mdpi.net/ec/papers/ecsoc6/187/Jamp2002.htm.
31. Frisch, M.J.; Trucks, G.W.; Schlegel, H.B.; et al. Gaussian 98 (Revision A.9), Gaussian Inc., Pittsburgh, PA, 1998.
32. Frisch, M.J.; Trucks, G.W.; Schlegel, H.B.; et al. Gaussian 03 (Revision B.03), Gaussian Inc., Pittsburgh, PA, 2003
33. Becke, A.D.J. Chem. Phys., 1993, 98, 5648.
34. Hesper, B.H.; Merz, K.M.; Kolman, P.A. J. Comp. Chem., 1990, 11, 431.
35. Singh, U.C.; Kolman, P.A. J. Comp. Chem., 1984, 5, 129.
36. Barone, V.; Cossi, M. J Phys. Chem. A, 1998, 102, 1995.
37. Stewart, J.J.P. J. Comp. Chem., 1989, 10, 209.
38. Stewart, J.J.P. J. Comp. Chem., 1989, 10, 221.
39. Dlabal, K.; Palát, K.; Lyčka, A.; Odlerová, Ž . Collect. Czech. Chem. Commun., 1990, 55, 2493.
40. Sato, N.; Arai, S. J. Heterocycl. Chem., 1982, 19, 407.
41. Swain, C.G.; Lupton, E.C. J. Amer. Chem. Soc., 1968 90, 4328.