An efficient synthesis of (E)-(2-arylpyrazino[1,2-a]pyrimidine-4-ylidene)acetonitriles and cyanomethyl appended pyrimidines

Tetrahedron Letters

Volumn 48, Issue 4, 2007, Pages 549-553

  Pratap, Ramendra ^a   Prakash Kushwaha, Shom ^a   Goel, Atul ^a   Ram, Vishnu Ji ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

2H Pyran 2 ones; 4 Pyrimidinyl acetonitrile; Pyrazino 1,2 a pyrimidines; Ring transformation

Indexed keywords

(PYRAZINO[1,2 A]PYRIMIDIN 4 YLIDENE)ACETONITRILE DERIVATIVE; 2 AMINOPYRAZINE; 2 PYRONE DERIVATIVE; ACETONITRILE DERIVATIVE; AMIDINE; AMINOACETONITRILE; AROMATIC AMINE; BASE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRAZINE DERIVATIVE; PYRIMIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; STEREOCHEMISTRY; SYNTHESIS;

EID: 33845624218     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.11.136     Document Type: Article

References (43)

1. Trepanier D.L., Rampy L.W., Shriver K.L., Eble J.N., and Shea P.J. J. Med. Chem. 11 (1968) 1045
2. Andres, C. J.; Scola, P. M.; Grant-Young, K. A. U. S. Patent 222158, 2005; Chem. Abstr. 2005, 143, 360126g.
3. Matsutani, S.; Mizushima, Y. EP 329126, 1989; Chem. Abstr. 1990, 112, 98557r.
4. Trepanier, D. L. (Dow Chemical Co.) U. S. Patent 3558,618, January 1971; Chem. Abstr. 1971, 74, 141870y.
5. Flohr, S.; Stengelin, S.; Gossel, M.; Klabunde, T.; Stahl, P.; Safar, P.; Spoonamore, J.; Smrcina, M.; Klein, J. T.; Merriman, G. H.; Whiteley, B. K.; Lanter, C.; Bordeau, K. J.; Yang, Z., Ger. Offen. DE 10,305,885, 26 August 2004; Chem. Abstr. 2004, 141, 225526f.
6. Kim J.-W., Cho J.-H., Han T., Lee J., and Oh C.-H. Bull. Korean Chem. Soc. 27 (2006) 484
7. Denin F., Blondeau D., and Sliwa H. J. Heterocycl. Chem. 27 (1990) 1639
8. Stanovnik B., van de Bovenkamp H., Svete J., Havala A., Simonič I., and Tišler M. J. Heterocycl. Chem. 27 (1990) 359
9. Toplak R., Svete J., Grdadolnik S.G., and Stanovnik B. Collect. Czech. Chem. Commun. 64 (1999) 177
10. Lennig, P.; Stengelin, S.; Klabunde, T.; Gossel, M.; Safar, P.; Smrcina, M.; Spoonamore, J.; Merriman, G.; Klein, J. T.; Whiteley, B.; Lanter C.; Bordeau, K.; Yang, Z. PCT Int. Appl. 2006, WO 2006, 24390; Chem. Abstr. 2006, 144, 274545g.
11. Brown D.J. In: Weissberger A. (Ed). The Chemistry of Heterocyclic Compounds. The Pyrimidines Vol. 16 (1970), Wiley-Interscience, New York
12. Lister J.H. In: Weissberger A., and Taylor E.C. (Eds). The Chemistry of Heterocyclic Compounds. Fused Pyrimidines, Part II, The Purines Vol. 24 (1971), Wiley-Interscience, New York
13. Hoffmann M.G. In: Schaumann E. (Ed). Houben-Weyl, Methoden der Organischen Chemie Vol. E9 (1996), G. Thieme, Stuttgart
14. Hurst D.T. An Introduction to the Chemistry and Biochemistry of Pyrimidines, Purines and Pteridines (1980), Wiley, Chichester
15. Bojarski J.T., Mokrosz J.L., Barton H.J., and Paluchowska M.H. Adv. Heterocycl. Chem. 38 (1985) 229
16. Brown D.J. In: Katritzky A.R., and Rees C.W. (Eds). Comprehensive Heterocyclic Chemistry Vol. 3 (1984), Pergamon Press, Oxford, New York, Toronto, Sydney, Paris, Frankfurt Chapter 2.13
17. Lehn J.-M. Supramolecular Chemistry-Concepts and Perspectives (1995), VCH, Weinheim Chapter 9
18. Hanan G.S., Volkmer D., Schubert U.S., Lehn J.-M., Baum G., and Fenske D. Angew. Chem., Int. Ed. 36 (1997) 1842
19. Semenov A., Spatz J.P., Möller M., Lehn J.-M., Sell B., Schubert D., Weidl C.H., and Schubert U.S. Angew. Chem., Int. Ed. 38 (1999) 2547
20. Harriman A., and Ziessel R. Coord. Chem. Rev. 171 (1998) 31
21. Harriman A., and Ziessel R. Chem. Commun. (1996) 1707
22. Eddington N.D., Cox D.S., Roberts R.R., Butcher R.J., Edafiogho I.O., Stables J.P., Cooke N., Goodwin A.M., Smith C.A., and Scott K.R.. Eur. J. Med. Chem. 37 (2002) 635
23. Eddington N.D., Cox D.S., Roberts R.R., Stables J.P., Powell C.B., and Scott K.R. Curr. Med. Chem. 7 (2000) 417
24. Scott K.R., Rankin G.O., Stables J.P., Alexander M.S., Edafiogho I.O., Farrar V.A., Kolen K.R., Moore J.A., Sims L.D., and Tonnut A.D. J. Med. Chem. 38 (1995) 4033
25. Edafiogho I.O., Alexander M.S., Moore J.A., Farrar V.A., and Scott K.R. Curr. Med. Chem. 1 (1994) 159
26. Dannhardt G., Bauer A., and Nowe U. Arch. Pharm. 330 (1997) 74
27. Ahluwalia V.K., Kaila N., and Bala S. Indian J. Chem., Sect. B 26B (1987) 700
28. Keutzberger A., and Gillessen J. Arch. Pharm. 318 (1985) 370
29. Eicher T., and Hauptmann S. Chemie der Heterocyclen (1994), Georg Thieme, Stuttgart, New York pp 398
30. Gilchrist T.L. In: Neunhoeffer H. (Ed). Heterocyclenchemie (1995), Wiley-VCH, New York 270
31. For an efficient repetitive synthesis of (oligo)pyrimidines based upon vinamidinium salt amidine condensations, see:. Gompper R., Mair H.-J., and Polborn K. Synthesis (1997) 696
32. Bredereck H., Gompper R., and Morlock G. Chem. Ber. 90 (1957) 942
33. Bredereck H., Gompper R., Schuh H.G., and Theilig G. Angew. Chem. 71 (1959) 753
34. Iuhas P.C., Georgescu E., Georgescu F., Draghici C., and Caproiu T.M. Rev. Roum. Chim. 46 (2001) 55
35. Matsunaga T., Tohda Y., and Ariga M. J. Chem. Soc., Perkin Trans. 1 (2000) 27
36. Dodson R.M., and Seyler J.K. J. Org. Chem. 16 (1951) 461
37. Al-Hajjar F.H., and Sabri S.S. J. Heterocycl. Chem. 19 (1982) 1087
38. Simon D., Lafont O., Farnoux C.C., and Miocque M. J. Heterocycl. Chem. 22 (1985) 1551
39. Boykin D.W., Kumar A., Bajic M., Xiao G., Wilson W.D., Bender B.C., McCurdy D.R., Hall J.E., and Tidwell R.R. Eur. J. Med. Chem. 32 (1997) 965
40. Ram V.J., Verma M., Hussaini F.A., and Shoeb A. Liebigs Ann. Chem. (1991) 1229
41. Ram V.J., Verma M., Hussaini F.A., and Shoeb A. J. Chem. Res. (S) (1991) 98
42. Ram V.J., Nath M., Srivastava P., Sarkhel S., and Maulik P.R. J. Chem. Soc., Perkin Trans. 1 (2000) 3719
43. 4 272.10619, found 272.10665.