Bicyclic [b]-Heteroannulated Pyridazine Derivatives. 10. Acid Cleavage of Some Beta-Keto Esters in the Reaction with 4,4-Dimethyl- and 4-Penyltetrahydropyridazine-3,6-dione 3-Hydrazones

• Autorzy: Wejroch K. , Karolak-Wojciechowska J. , Lange J. , Sośnicki J. G.
• Języki publikacji: EN

Abstrakty

EN

4,4-Dimethyltetrahydropyridazine-3,6-dione 3-hydrazone (1) reacted with _-keto esters in refluxing ethanol to give the acid cleavage products: 7,8-dihydro-3,8,8-trimethyltriazolo[ 4,3-b]pyridazin-6(5H)-one (7) and esters 9. The yield of the reaction in most cases was nearly quantitative. At room temperature mostly the simple condensation products 4 were isolated. In analogous reactions, 4-phenyltetrahydropyridazine-3,6- dione 3-hydrazone (2) was found to be much less reactive. The hydrazone-ester condensation products 4 and some 5 were converted into the corresponding pyrazolylpyridazine derivatives 10 and 11, respectively, by heating above their melting points; the formation of 7 was noted in the reactions with 4. The results support the concept of different tautomeric preferences in 1 and 2.

Słowa kluczowe

EN

Beta-keto esters; acid cleavage; pyridazine-3,6-dione 3-hydrazone

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2002
• Tom: Vol. 76 / nr 11
• Strony: 1577--1586
• Opis fizyczny: Bibliogr. 12 poz., rys.

Twórcy

autor

Wejroch K.

• Department of Chemistry, University of Technology, Noakowskiego 3, 00-664 Warsaw, Poland

autor

Karolak-Wojciechowska J.

• Institute of General and Ecological Chemistry, Technical University, Żwirki 36, 90-924 Łódź, Poland

autor

Lange J.

• Department of Chemistry, University of Technology, Noakowskiego 3, 00-664 Warsaw, Poland

autor

Sośnicki J. G.

• Institute of Chemistry and Environmental Protection, Technical University

Bibliografia

• 1. Lange J., Tondys H., Koberda W. and Gniewosz M., Synth. Commun., 23, 1371 (1993).
• 2. Lange J., Karolak-Wojciechowska J., Gniewosz M. and Plenkiewicz J., Pharmazie, 49, 21 (1994).
• 3. Lange J., Karolak-Wojciechowska J., Pytlewska E., Plenkiewicz J., Kuliński T. and Rump S., J. Heterocycl. Chem., 34, 389 (1997).
• 4. Wejroch K,, Karolak-Wojciechowska J., Lange J., Sośnicki J., Jagodziński T. and Kielak A., J. Heterocycl. Chem., 38, 877 (2001).
• 5. Kaupp G., Frey H. and Behmann G., Synthesis, 555 (1985).
• 6. Joshi K.C. and Chand P., Heterocycles, 16, 43 (1981). 
• 7. DomeanuM., Stefanescu E. and GiosuG., Rev. Med.-Chir., 91,541 ( 1987); Chem. Abstr., 109,170343a (1988).
• 8. Zimmer H. and Amer A., Heterocycles, 26, 1177 (1987).
• 9. Sawhney S.N., Sharmla P.K. and Gupta A., Indian J. Chem., 31B, 421 (1992).
• 10. Alaka B.V., Patnaik D. and Rout M.K., J. Indian Chem. Soc., 59, 1168 (1982).
• 11. Sheldrick G.M., SHELXS-97-2. Program for the Solution of Crystal Structures from Diffraction Data. University of Göttingen, Germany, 1997.
• 12. Sheldrick G.M., SHELXL-97-2. Program for the Refinement of Crystal Structures from Diffraction Data. University of Gottingen, Germany, 1997.