Study on the cyclization of 6-arylethynylpyrimidine-5-carbaldehydes with tert-butylamine: microwave versus thermal preparation of pyrido[4,3-d]pyrimidines

Tetrahedron

Volumn 65, Issue 29-30, 2009, Pages 5752-5759

  Cikotiene, Inga ^a   Kairys, Visvaldas ^b   Buksnaitiene, Rita ^a   Morkunas, Marius ^a   Rudys, Simonas ^a   Brukstus, Algirdas ^a   Fernandes, Miguel X ^b  

^a VILNIUS UNIVERSITY   (Lithuania)

^b UNIVERSITY OF MADEIRA   (Portugal)

Author keywords

[No Author keywords available]

Indexed keywords

2 METHYLTHIO 7 PHENYL 4 PYRROLIDIN 1 YLPYRIDO[4,3 D]PYRIMIDINE; 4 AMINO 7 (4 ETHYLPHENYL) 2 METHYLTHIOPYRIDO[4,3 D]PYRIMIDINE; 4 AMINO 7 (4 THYLPHENYL) 2 METHYLTHIOPYRIDO[4,3 D]PYRIMIDINE; 4 ANILINO 2 METHYLTHIO 7 PHENYLPYRIDO[4,3 D]PYRIMIDINE; 4 ANILINO 7 (4 ETHYLPHENYL) 2 METHYLTHIOPYRIDO[4,3 D]PYRIMIDINE; 4 N BENZYLAMINO 2 METHYLTHIO 7 PHENYLPYRIDO[4,3 D]PYRIMIDINE; 4 N BENZYLAMINO 7 (4 ETHYLPHENYL)PYRIDO[4,3 D]PYRIMIDINE; 4 N BENZYLAMINO 7 PHENYLPYRIDO[4,3 D]PYRIMIDINE; 4 N ETHYLAMINO 2 METHYLTHIO 7 PHENYLPYRIDO[4,3 D]PYRIMIDINE; 4 N METHYLAMINO 2 METHYLTHIO 7 PHENYLPYRIDO[4,3 D]PYRIMIDINE; 7 (4 ETHYLPHENYL) 2 METHYLTHIO 4 PIPERIDIN 1 YLPYRIDO[4,3 D]PYRIMIDINE; 7 (4 ETHYLPHENYL) 2 METHYLTHIO 4 PYRROLIDIN 1 YLPYRIDO[4,3 D]PYRIMIDINE; 7 (4 FLUOROPHENYL) 2 METHYLTHIO 4 MORFOLIN 4 YLPYRIDO[4,3 D]PYRIMIDINE; 7 (4 FLUOROPHENYL) 2 METHYLTHIO 4 PYRROLIDIN 1 YLPYRIDO[4,3 D]PYRIMIDINE; 7 PHENYL 4 MORPHOLIN 4 YLPYRIDO[4,3 D]PYRIMIDINE; 7 PHENYL 4 PYRROLIDIN 1 YLPYRIDO[4,3 D]PYRIMIDINE; ALDEHYDE DERIVATIVE; BUTYLAMINE; PYRIMIDINE DERIVATIVE; TERT BUTYLAMINE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; CYCLIZATION; DRUG SYNTHESIS; HEATING; INTERMETHOD COMPARISON; MICROWAVE RADIATION; PRIORITY JOURNAL;

EID: 84961978655     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.05.015     Document Type: Article

References (35)

1. In: Stang P.J., and Diederich F. (Eds). Modern Acetylene Chemistry (1995), VCH, Weinheim, Germany
2. In: Patai S. (Ed). Chemistry of Triple-Bonded Functional Groups (1994), Wiley, New York, NY
3. Takeda A., Kamijo S., and Yamamoto Y. J. Am. Chem. Soc. 122 (2000) 5662
4. Gabriele B., Salerno G., and Fazio A. Org. Lett. 2 (2000) 351
5. Arcadi A., Cacchi S., Del Rosario M., Fabrizi G., and Marinelli F. J. Org. Chem. 61 (1996) 9280
6. Cacchi S., Fabrizi G., and Moro L. Tetrahedron Lett. 39 (1998) 5101
7. Roesh K.R., and Larock R.C. Org. Lett. 1 (1999) 553
8. Roesh K.R., and Larock R.C. J. Org. Chem. 67 (2002) 86
9. Dai G., and Larock R.C. Org. Lett. 3 (2001) 4035
10. Dai G., and Larock R.C. Org. Lett. 4 (2002) 193
11. Zhang H., and Larock R.C. J. Org. Chem. 67 (2002) 7048
12. Huang Q., Hunter J.A., and Larock R.C. Org. Lett. 3 (2001) 2973
13. Huang Q., Hunter J.A., and Larock R.C. J. Org. Chem. 67 (2002) 3437
14. Susvilo I., Brukstus A., and Tumkevicius S. Synlett (2003) 1151
15. Tumkevicius S., Susvilo I., and Brukstus A. Chem. Heterocycl. Comp. (2004) 1546
16. Cikotiene I., Morkunas M., Motiejaitis D., Rudys S., and Brukstus A. Synlett (2008) 1693
17. Cikotiene I., and Morkunas M. Synlett (2009) 284
18. Susvilo I., Palskyte R., Tumkevicius S., and Brukstus A. Chem. Heterocycl. Comp. (2004) 489
19. Raymond E., Faivre S., and Armand J.P. Drugs 60 (2000) 15
20. Smaill J.B., Palmer B.D., Rewcastle G.W., Denny W.A., McNamara D.J., Dobrusin E.M., Bridges A.J., Zhou H., Showalter H.D.H., Winters R.T., Leopold W.R., Fry D.W., Nelson J.M., Slintak V., Elliot W.L., Roberts B.J., Vincent P.W., and Patmore S.J. J. Med. Chem. 42 (1999) 1803
21. Jang M.J., de Jonghe S., Gao L.J., Rozenski J., and Herdewijn P. Eur. J. Med. Chem. (2006) 4257
22. Cikotiene I., Morkunas M., Rudys S., Buksnaitiene R., and Brukstus A. Synlett (2008) 2799
23. Synfacts (2009) 16 (highlighted by)
24. Clark J., Shahhet M.S., Korakas D., and Varvounis G. J. Heterocycl. Chem. (1993) 1065
25. Kasparec J., Adams J.L., Sisko J., and Silva D. Tetrahedron Lett. 44 (2003) 4567
26. Cikotiene I., Pudziuvelyte E., Brukstus A., and Tumkevicius S. Tetrahedron 63 (2007) 8145
27. Becke A.D. J. Chem. Phys. 98 (1993) 5648
28. Lee C., Yang W., and Parr R.G. Phys. Rev. B 37 (1988) 785
29. Hehre W.J., Ditchfield R., and Pople J.A. J. Chem. Phys. 14 (1978) 91
30. Harihanan P.C., and Pople J.A. Theor. Chim. Acta 28 (1973) 213
31. Miertus S., Scrocco E., and Tomasi J. J. Chem. Phys. 55 (1981) 117
32. Cossi M., Barone V., Cammi R., and Tomasi J. J. Chem. Phys. Lett. 225 (1996) 327
33. Cances E., Mennucci B., and Tomasi J. J. Chem. Phys. 107 (1997) 3032
34. Schmidt M.W., Baldridge K.K., Boatz J.A., Elbert S.T., Gordon M.S., Jensen J.H., Koseki S., Matsunaga N., Nguyen K.A., Su S., Windus T.L., Dupuis M., and Montgomery Jr. J.A. J. Comput. Chem. 14 (1993) 1347
35. Laurence C., Nicolet P., Dalati M.T., Abboud J.-L.M., and Notario R. J. Phys. Chem. 98 (1994) 5807