The preparation of 1H-pyrazole-1-carboxylic acid, 1,1-dimethylethyl esters from dilithiated C(α),N-hydrazones of hydrazinecarboxylic acid, 1,1-dimethylethyl ester

Synthetic Communications

Volumn 26, Issue 19, 1996, Pages 3659-3669

  Church, A Cameron ^a   Koller, Madlene U ^a   Hines, Margaret A ^a   Beam, Charles F ^a  

^a School of Business   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PYRAZOLE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029788412     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919608003780     Document Type: Article

References (37)

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7. The trimetalation of C(α),N-hydrazones requires more time than dimetalation of C(α),N-carboalkoxyhydrazones, and the latter entry compounds are usually easier to prepare. See also: (a) Newkome, G.P. and Fishel, D.C., J. Org. Chem., 1966, 31, 677. (b) Lock, G. and Stach, K., Ber., 1944, 77B, 293. Harnsberger, H.F., Cochran, E.L., and Szmant, H.H., J. Am. Chem. Soc., 1955, 77, 5048.
8. The trimetalation of C(α),N-hydrazones requires more time than dimetalation of C(α),N-carboalkoxyhydrazones, and the latter entry compounds are usually easier to prepare. See also: (a) Newkome, G.P. and Fishel, D.C., J. Org. Chem., 1966, 31, 677. (b) Lock, G. and Stach, K., Ber., 1944, 77B, 293. Harnsberger, H.F., Cochran, E.L., and Szmant, H.H., J. Am. Chem. Soc., 1955, 77, 5048.
9. The trimetalation of C(α),N-hydrazones requires more time than dimetalation of C(α),N-carboalkoxyhydrazones, and the latter entry compounds are usually easier to prepare. See also: (a) Newkome, G.P. and Fishel, D.C., J. Org. Chem., 1966, 31, 677. (b) Lock, G. and Stach, K., Ber., 1944, 77B, 293. Harnsberger, H.F., Cochran, E.L., and Szmant, H.H., J. Am. Chem. Soc., 1955, 77, 5048.
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19. (e) Brewbaker, J.L. and Hart, H., J. Am. Chem. Soc., 1969, 91, 711.
20. 1H-Pyrazole-1-carboxylic acids, 1,1-dimethylethyl ester, recent citations: (a) Barluenga, J., Rubio, E., Rubio, V., Muniz, L., Iglesias, M., and Gotar, V., J. Chem. Res. Synap., 1985, 124. (b) Al-Hajjar, F.S., and Sabri, S.S., J. Heterocycl. Chem., 1986, 23, 727. Gerus, I.I., Gorbunova, M.G., Vdovenko, V.P., Yagupol'skii, Y.L., and Kukhar, V.P., Zh. Org. Khim., 1990, 26, 1877. (d) Attanasi, O.A., Filippone, P., and Mei, A., Tetrahedron, 1992, 48, 1707.
21. 1H-Pyrazole-1-carboxylic acids, 1,1-dimethylethyl ester, recent citations: (a) Barluenga, J., Rubio, E., Rubio, V., Muniz, L., Iglesias, M., and Gotar, V., J. Chem. Res. Synap., 1985, 124. (b) Al-Hajjar, F.S., and Sabri, S.S., J. Heterocycl. Chem., 1986, 23, 727. Gerus, I.I., Gorbunova, M.G., Vdovenko, V.P., Yagupol'skii, Y.L., and Kukhar, V.P., Zh. Org. Khim., 1990, 26, 1877. (d) Attanasi, O.A., Filippone, P., and Mei, A., Tetrahedron, 1992, 48, 1707.
22. 1H-Pyrazole-1-carboxylic acids, 1,1-dimethylethyl ester, recent citations: (a) Barluenga, J., Rubio, E., Rubio, V., Muniz, L., Iglesias, M., and Gotar, V., J. Chem. Res. Synap., 1985, 124. (b) Al-Hajjar, F.S., and Sabri, S.S., J. Heterocycl. Chem., 1986, 23, 727. Gerus, I.I., Gorbunova, M.G., Vdovenko, V.P., Yagupol'skii, Y.L., and Kukhar, V.P., Zh. Org. Khim., 1990, 26, 1877. (d) Attanasi, O.A., Filippone, P., and Mei, A., Tetrahedron, 1992, 48, 1707.
23. 1H-Pyrazole-1-carboxylic acids, 1,1-dimethylethyl ester, recent citations: (a) Barluenga, J., Rubio, E., Rubio, V., Muniz, L., Iglesias, M., and Gotar, V., J. Chem. Res. Synap., 1985, 124. (b) Al-Hajjar, F.S., and Sabri, S.S., J. Heterocycl. Chem., 1986, 23, 727. Gerus, I.I., Gorbunova, M.G., Vdovenko, V.P., Yagupol'skii, Y.L., and Kukhar, V.P., Zh. Org. Khim., 1990, 26, 1877. (d) Attanasi, O.A., Filippone, P., and Mei, A., Tetrahedron, 1992, 48, 1707.
24. Pyrazoles and related heterocyclic compounds are well documented (Chemical Abstracts) for their agricultural potential as herbicides, fungicides, bacteriocides, insecticides, and plant growth stimulators. See also: Chene, A., Peignier, R., Vors, J.P., Mortier, J., Cantegril, R., and Croisat, D., Eur. Pat. Appl. EP 538,156, 1991; Chem. Abstr., 1993, 119, P 160271t.
25. Pyrazoles and related heterocyclic compounds are well documented (Chemical Abstracts) for their agricultural potential as herbicides, fungicides, bacteriocides, insecticides, and plant growth stimulators. See also: Chene, A., Peignier, R., Vors, J.P., Mortier, J., Cantegril, R., and Croisat, D., Eur. Pat. Appl. EP 538,156, 1991; Chem. Abstr., 1993, 119, P 160271t.
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27. Mirone, P and Vampiri, M., Atti Accad. Nazl. Lincei, Rend. Classe Sci. Fis., Mat. e Nat., 1952, 12, 583; Chem. Abstr., 1952, 46, 9423.
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31. All chemicals were purchased from Aldrich Chemical Co.
32. 3), and 6.40-8.18 (m, ArH and NH).
33. Microanalyses for C, H, and N were obtained from Quantitative Technologies, Inc., Box 470, Salem Industrial Park, Whitehouse, NJ 08888 and Robertsons Laboratory, 29 Samson Avenue, Madison, NJ 07940 [Compd. No. from Table]. Calcd.for 1: C, 69.38; H, 5.56; N, 7.36. Found: C, 69.12; H, 5.58; N, 7.40. Calcd. for 2: C, 68.79; H, 6.47; N, 6.42. Found: C, 68.85; H, 6.46; N, 6.29. Calcd. for 3 (solvated): C, 72.23; H, 6.50; N, 7.32. Found: C, 72.43, 72.17; H, 6.78, 6.63; N, 7.09. Calcd. for 4: C, 69.31; H, 6.71; N, 6.21. Found: C, 69.01; H, 6.67; N, 6.17. Calcd. for 5: C, 65.54; H, 5.50; N, 7.28. Found: C, 65.73; H; 5.42; N, 7.30. Calcd. for 6: C, 62.09; H, 5.66; N, 6.30. Found: C, 61.91; H, 5.59; N, 6.24. Calcd. for 7: C, 65.54; H, 5.50; N, 7.28. Found: C, 65.54; H, 5.52; N, 7.33. Calcd. for 8 (solvated): C, 62.87; H, 6.59; N, 6.11. Found: C, 62.88; H, 6.78; N, 6.03. Calcd. for 9: C, 65.44; H, 6.41; N, 6.36. Found: C, 65.50; H, 6.48; N, 6.21. Calcd. for 10: C, 69.21; H, 7.74; N, 10.76. Found: C, 69.31; H, 7.68; N, 10.70. Calcd. for 11: C, 70.04; H, 8.08; N, 10.21. Found: C, 70.07; H, 8.23; N, 10.16. Calcd. for 12: C, 58.10; H, 6.38; N, 10.43. Found: C, 58.24; H, 6.52; N, 10.43. Calcd. for 13: C, 63.62; H, 7.63; N, 10.60. Found: C, 63.87; H, 7.47; N, 10.63. Calcd. for 14: C, 63.62; H, 7.63; N, 10.60. Found: C, 63.73; H, 7.61; N, 10.52. Calcd. for 15: C, 62.38; H, 7.25; N, 11.19. Found: C, 62.38; H, 7.27; N, 11.23. Calcd. for 16: C, 67.91; H, 6.65; N, 6.60. Found: C, 67.80; H, 6.62; N, 6.49.
34. We would anticipate cleavage of the carbo-t-butoxy group under these conditions.
35. Higher melting point N-H pyrazoles, if present, would have easily been isolated andidentified. See ref. 2.
36. (a) Park, D.J., Fulmer, T.D., and Beam, C.F., J. Heterocycl. Chem., 1981, 18, 649.
37. (b) Mack, H.M., Davis, E.A., Kadkhodayan, B., Taylor, R.A., Duncan, D.C., and Beam, C.F., J. Heterocycl. Chem., 1987, 24, 1733.