A short and expeditious regiospecific synthesis of novel pyrazoles

Journal of Chemical Research - Part S

Volumn , Issue 11, 2003, Pages 746-748

  Chowdhury, S K Dutta ^a   Sarkar, Mili ^b   Mahalanabis, Kumar K ^c  

^a Jogesh Chandra Chaudhuri College   (India)

^b GURUDAS COLLEGE   (India)

^c JADAVPUR UNIVERSITY   (India)

Author keywords

Pyrazoles; cyanoenaminones; aminocrotononitrile

Indexed keywords

AMINE; NITRILE; PYRAZOLE DERIVATIVE;

ACYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 1342332607     PISSN: 03082342     EISSN: None     Source Type: Journal    
DOI: 10.3184/030823403322863184     Document Type: Article

References (41)

1. J. Elguero, Pyrazoles, in Comprehensive Heterocyclic Chemistry II, A.R. Katritzky, E.F.V. Scriven, and C.W. Rees, eds, Vol. 3, ed. I. Shinkai, Elsevier Science Ltd, Oxford, 1996, pp. 1-75.
2. (a) J.A. Picard, B.D. Roth and D.R. Sliskovic, U.S.P. 4 957 971 (Cl. 514-252; C07 D 403/04), 18 Sep 1990, US Appl. 882 327, 07 Jul 1986; 15pp. Chem. Abstr., 1991, 114, 185 784x;
3. (b) W.V. Murray and M.P. Wachter, Eur. Pat. Appl. EP 293 220 (Cl. C07 D 231/12), 30 Nov 1988, US Appl. 55 806, 29 May 1987; Chem. Abstr., 1989, 111, 23 508w;
4. (c) E.E. Allen, W.J. Greenlee, M. MacCoss and W.T. Ashton, PCT Int. Appl. WO 91 15 479 (Cl. C0 7D 261/08), 17 Oct 1991, US Appl. 501 469, 30 Mar 1990; 171 pp. Chem. Abstr., 1992, 116, 106 284z;
5. (d) Y.R. Huang and J.A. Katzenellenbogen, Org. Lett., 2002, 2, 2833.
6. J. Stetter, R. Gehring, O. Schallner, H.J. Santel, R.R. Schmidt, and K. Luerssen, (Bayer A.-G.) Ger. Offen., DE 3 625 686 (Cl. C07 D 231/22), 04 Feb 1988, Appl. 30 Jul 1986; 4pp. Chem. Abstr., 1988, 108, 167 465r.
7. P. Ooms and B. Becker, (Bayer A.-G.) Ger. Offen. DE 3 706 993 (Cl. C07 D 231/38), 15 Sep 1988, Appl. 05 Mar 1987; 19 pp. Chem. Abstr., 1989, 110, 38 988f.
8. U. Jensen-Korte, O. Schallner, J. Stetter, H.J. Wroblowsky, W. Stendel, B. Becker, B. Homeyer, and W. Behrenz, (Bayer A.-G.) Ger. Offen. DE 3 600 287 (Cl. C07 D 231/22) 16 Jul 1987, Appl. 08 Jan 1986, 28 pp. Chem. Abstr., 1988, 108, 6015d.
9. rd 1985 (Pub 1987). 5, 410-13 (Eng). VCH: Weinheim, Chem. Abstr., 1989, 110, 135 140f.
10. rd 1985 (Pub 1987). 5, 410-13 (Eng). VCH: Weinheim, Chem. Abstr., 1989, 110, 135 140f.
11. K. Izumi, T. Kitamikado, and S. Sugiura, J. Pharm. Soc. Japan 1973, 93, 1349.
12. Y. Ribeill, S. Huber, S.M. McComb, M.J. Malaska, D. Chou, and D.L.A. Perez, PCT Int. Appl. WO 60 35 884 (Cl. C07 D 231/44), 22 Jun 2000, US Appl. PV 140 680, 24Jun 1999; 62pp. Chem. Abstr., 2000, 133, 58 800s.
13. L.A. Paquette, in Principles of Modern Heterocyclic Chemistry, Benjamin-Cummings, Inc., 1968, Chapter 6, p187.
14. C.L. Habraken and J.A. Moore, J. Org. Chem., 1965, 30, 1892.
15. J.V. Greenhill, Chem. Soc. Rev., 1997, 6, 277.
16. (a) W.S. Murphy and M. Bertrand, J. Chem. Soc., Perkin Trans. 1, 1998, 4115;
17. (b) S. Krischbaum and H. Waldmann, J. Org. Chem.,. 1998, 63, 4936;
18. (c) A.W. Trautwein and G. Jung, Tetrahedron Lett., 1998, 39, 8263;
19. (d) N. Nishimura, Y. Koyano, M. Sugiura, and I. Maeba, Heterocycles, 1999, 51, 803;
20. (e) I. Maeba, Y. Nishiyama, S. Kanazawa, and A. Sato, Heterocycles, 1995, 41, 507;
21. (f) Y. Nishiyama, N. Nishimura, N. Kuroyanagi, and I. Maeba, Carbohydrate Res., 1997, 300, 283;
22. (g) N. Nishimura, M. Bauno, A. Maki, Y. Nishiyama, and I. Maeba, Carbohydrate Res., 1998, 307, 211;
23. (h) I. Maeba, Y. Ito, M. Wakimura, and C. Ito, Heterocycles, 1993, 36, 1617, 2805.
24. (a) A.R. Katritzky, R.A. Barcock, Q.H. Long, M. Balasubramanian, N. Malhotra, and J.V. Greenhill, Synthesis, 1993, 233;
25. (b) G. Bartoli, C. Cimarelli, G. Palmieri, M. Bosco and R. Dalpozzo, Synthesis, 1990, 895;
26. (c) S. El Cherif and L. Rene, Synthesis, 1988, 138;
27. (d) C. Cartaya-Maria, D.G. Henderson, and R.W. Soeder, Synth. Commun., 1997, 4275;
28. (e) A.R. Katritzky, Y. Fang, A. Donkier, and J. Xu, Synthesis, 2002, 2029;
29. (f) A. Alberola, L.F. Antolin, A.M. Gonzalez, M.A. Laguna, and F.J. Pulido, Heterocycles, 1987, 25, 393.
30. K.K. Mahalanabis, M. Sarkar, S.K. Dutta Chowdhury and C.R. Ghosal, Ind. J. Chem., 2002, 41B, 1902.
31. V.D. Piaz, G. Ciciani, and S. Chimichi, Heterocycles, 1985, 23, 365.
32. (a) B. Liu, M.-X. Wang, and Z.-T. Huang, Tetrahedron Lett. 1999, 40, 7399;
33. (b) A.A.M. Al-Shiekh, Al-Zaydi K. Mohamed, and E. Abdel-Aziz Hafez, J. Chem. Res.(M), 2000, 173
34. (c) Al-Afaleq and I. Eljazi,. Synth. Commun., 2000, 30, 1985;
35. (d) A.G.A. Elagamey and F.M.A. El-Taweel, J. Prakt. Chem., 1991, 333.
36. H. Adkins and G.M. Whitman, J. Am. Chem. Soc., 1942, 64, 150.
37. (a) H.C. Brown, J. Chem. Soc., 1938, 60, 1325;
38. (b) Org. Synth. Coll. Vol. 3, ed. E.C. Homing, John Wiley and Sons Inc. New York; Chapman and Hall, London, Ltd. 1955, pp. 29, 714;
39. rd Edition, ELBS and Longman, 1973, p. 121, p. 791.
40. A.I. Vogel, in A Text Book of Practical Organic Chemistry, 3rd edn, ELBS and Longman, 1973, p. 121.
41. E. Benary and M. Hosenfeld, Ber., 1922, 55, 3417.