Reaction between isocyanides and dialkyl acetylenedicarboxylates in the presence of 2,4-dihydro-3H-pyrazol-3-ones. One-pot synthesis of highly functionalized 7-oxo-1H,7H-pyrazolo[1,2-a]pyrazoles

Tetrahedron

Volumn 61, Issue 16, 2005, Pages 3963-3966

  Adib, Mehdi ^a   Sayahi, Mohammad Hosein ^a   Aghaaliakbari, Behnaz ^b   Bijanzadeh, Hamid Reza ^c  

^a UNIVERSITY OF TEHRAN   (Iran)

^b UNIVERSITY OF KASHAN   (Iran)

^c TARBIAT MODARES UNIVERSITY   (Iran)

Author keywords

2,4 Dihydro 3H pyrazol 3 ones; 7 Oxo 1H,7H pyrazolo 1,2 a pyrazoles; Acetylenic esters; Isocyanides; Three component reactions

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; CYANIDE; DIETHYL 3 (CYCLOHEXYLAMINO) 5 METHYL 7 OXO 1H,7H PYRAZOLO[1,2 A]PYRAZOLE 1,2 DICARBOXYLATE; DIETHYL 3 (CYCLOHEXYLAMINO) 5 PHENYL 7 OXO 1H,7H PYRAZOLO[1,2 A]PYRAZOLE 1,2 DICARBOXYLATE; DIETHYL 3 (TERT BUTYLAMINO) 5 METHYL 7 OXO 1H,7H PYRAZOLO[1,2 A]PYRAZOLE 1,2 DICARBOXYLATE; DIETHYL 3 (TERT BUTYLAMINO) 5 PHENYL 7 OXO 1H,7H PYRAZOLO[1,2 A]PYRAZOLE 1,2 DICARBOXYLATE; DIMETHYL 3 (CYCLOHEXYLAMINO) 5 METHYL 7 OXO 1H,7H PYRAZOLO[1,2 A]PYRAZOLE 1,2 DICARBOXYLATE; DIMETHYL 3 (CYCLOHEXYLAMINO) 5 PHENYL 7 OXO 1H,7H PYRAZOLO[1,2 A]PYRAZOLE 1,2 DICARBOXYLATE; DIMETHYL 3 (TERT BUTYLAMINO) 5 METHYL 7 OXO 1H,7H PYRAZOLO[1,2 A]PYRAZOLE 1,2 DICARBOXYLATE; DIMETHYL 3 (TERT BUTYLAMINO) 5 PHENYL 7 OXO 1H,7H PYRAZOLO[1,2 A]PYRAZOLE 1,2 DICARBOXYLATE; PYRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; PRIORITY JOURNAL; SYNTHESIS;

EID: 19344370920     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.02.050     Document Type: Article

References (22)

1. J.F. Swinbourne, H.J. Hunt, and G. Klinkert Adv. Heterocycl. Chem. 23 1987 103
2. S. Radl A.R. Katritzky C.W. Rees E.V.F. Scriven Comprehensive Heterocyclic Chemistry 1996 Pergamon London 747 832 Chapter 8.31, and references therein
3. Y. Fujimura, Y. Shiraki, Y. Nawata, and I. Matsunaga J. Pharm. Soc. Jpn. 106 1986 1002
4. M.S. Hadley, F.D. King, B. McRitchie, and D.H. Turner Bioorg. Med. Chem. Lett. 2 1992 1293
5. J.M. Indelicato, and C.E. Pasini J. Med. Chem. 31 1988 1227
6. N.E. Allen, J.N. Hobbs, D.A. Preston, J.R. Turner, and C.Y.E. Wu J. Antibiot. 43 1990 92
7. L.N. Jungheim, D.B. Boyd, J.M. Indelicato, C.E. Pasini, D.A. Preston, and W.E. Alborn Jr. J. Med. Chem. 34 1991 1732
8. D.B. Boyd J. Med. Chem. 36 1993 1443
9. R.J. Ternansky, S.E. Draheim, A.J. Pike, F.T. Counter, J.A. Eudaly, and J.S. Kasher J. Med. Chem. 36 1993 3224
10. C. Turk, L. Golič, L. Selič, J. Svete, and B. Stanovnik Arkivoc (v) 2001 87
11. C. Turk, J. Svete, B. Stanovnik, L. Golič, S. Golič- Grdadolnik, A. Golobič, and L. Selič Helv. Chim. Acta 84 2001 146
12. A. El-Alali, and A.S. Al-Kamali Can. J. Chem. 80 2002 1293
13. I. Yavari, M. Adib, F. Jahani-Moghaddam, and H.R. Bijanzadeh Tetrahedron 58 2002 6901
14. I. Yavari, M. Adib, and M.H. Sayahi Tetrahedron Lett. 43 2002 2927
15. I. Yavari, M. Adib, and L. Hojabri Tetrahedron 58 2002 6895
16. I. Yavari, M. Adib, and M.H. Sayahi J. Chem. Soc., Perkin Trans. 1 13 2002 1517
17. I. Ugi Isonitrile Chemistry 1971 Academic London
18. I. Ugi Angew. Chem., Ed. Engl. 21 1982 810
19. A. Dömling, and I. Ugi Angew. Chem., Int. Ed. 39 2000 3168
20. V. Nair, A.U. Viond, J.S. Nair, A.R. Sreekanth, and N.P. Rath Tetrahedron lett. 41 2000 6675
21. H.M. Walborsky, and M.P. Presiasamy S. Patai Z. Rappaport The Chemistry of Functional Groups, Supplement C 1983 Wiley New York 835 837 Chapter 20
22. E.C. Taylor, R.L. Robey, D.K. Johnson, and A. McKillop Organic Synthesis Collect. Vol. 6 1988 Wiley New York pp 791