Abstract
The involvement of Mannich bases derived from ortho-hydroxyacetophenones in amine-exchange reactions with pyrazole and methyl- and/or halogen-substituted pyrazoles was studied. The corresponding β-(pyrazol-1-yl)ethyl ketones resulted in excellent yield and were characterized by elemental analysis, IR, and 1H and 13C NMR spectroscopy.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
REFERENCES
E. Comanita, I. Popovici, B. Comanita, and Gh. Roman, Bull. Inst. Politehn. Iasi, 46 (50), 19 (2000).
M. Tramontini, Synthesis, 703 (1973).
M. Tramontini and L. Angiolini, Tetrahedron, 46, 1791 (1990).
H. Ran and J. Ding, CN 1,107,474 (1994); Chem. Abstr., 124, 261038 (1996).
R. I. Ishmetova, V. G. Kitaeva, and G. L. Rusinov, Zh. Org. Khim., 31, 431 (1995).
R. Schaller, H. Ehrhardt, B. Sachse, B. Buerstell, H. Bieringer, and K. Klaus (Hoechst A.-G.), EP 132,771; Chem. Abstr., 103, 160511 (1985).
A. Popov, Zh. P. Piskunova, V. N. Matvienko, G. P. Kondratenko, and Yu. I. Nikolenko, Khim.-Farm. Zh., 23, 1232 (1989).
T. Maier and H. Mildenberger, Angew. Chem., 92, 128 (1980).
J. P. Dickens, G. J. Ellames, N. J. Hare, K. R. Lawson, W. R. McKay, A. P. Metters, P. L. Myers, A. M. S. Pope, and R. M. Upton, J. Med. Chem., 34, 2356 (1991).
F. Andreani, R. Andrisano, C. Della Casa, and M. Tramontini, Tetrahedron Lett., 1059 (1968).
D. F. Rane, A. G. Fishman, and R. E. Pike, Synthesis, 694 (1984).
K. Takahashi, S. Shimizu, and M. Ogata, Synth. Commun., 17, 809 (1987).
C. Rentzea, E. Ammermann, and E. H. Pommer (BASF A.-G.), DE 3,011,258; Chem. Abstr., 96, 35250 (1982).
L. Zirngibl, Antifungal Azoles, Wiley-VCH, New York (1998), p. 113.
E. Comanita, I. Popovici, B. Comanita, and Gh. Roman, ACH-Models Chem., 134, 3 (1997).
E. Comanita, Gh. Roman, I. Popovici, and B. Comanita, J. Serb. Chem. Soc., 66, 9 (2001).
E. Comanita, I. Popovici, Gh. Roman, G. Robertson, and B. Comanita, Heterocycles, 51, 2139 (1999).
C. Montigoul, M.-J. Richard, C. Vigne, and L. Giral, J. Heterocycl. Chem., 21, 1489 (1984).
J. Elguero, R. Jacquier, and H. C. N. Tien Due, Bull. Soc. Chim. Fr., 3727 (1966).
Gh. Roman, E. Comanita, B. Comanita, and C. Draghici, J. Serb. Chem. Soc., 63, 931 (1998).
Gh. Roman, D. Nanu, E. Comanita, and B. Comanita, Turk. J. Chem., 24, 67 (2000).
K. von Auwers and K. Bähr, J. Prakt. Chem. [2], 116, 65 (1927).
G. T. Morgan and I. Ackerman, J. Chem. Soc., 123, 1308 (1923).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Roman, G., Comanita, E. & Comanita, B. N-Alkylation of Pyrazoles with Mannich Bases Derived from ortho-Hydroxyacetophenones. Chemistry of Heterocyclic Compounds 38, 1072–1076 (2002). https://doi.org/10.1023/A:1021201214319
Issue Date:
DOI: https://doi.org/10.1023/A:1021201214319