Synthesis of pyrazoles and oxyquinoxalines from 2,4‐dioxohexenoales

Authors

H. El Khadem, Michigan Technological University
Zaki El‐Shafei, Alexandria University
Latif Rateb, Alexandria University
Hassan Mokhtar, Alexandria University

Document Type

Article

Publication Date

1-1-1973

Department

Department of Chemistry; Department of Chemical Engineering

Abstract

Condensation of ethyl 2,4‐dioxo‐6‐phenylhex‐5‐enoates (I; R = H, I; R = Me, I, R = Ph) with various hydrazines yielded ethyl 5‐styrylpyrazole‐3‐carboxylates (III), which were hydrolyzed to the acids (IV), and ozonized to 5‐keto pyrazole esters (VI) and acids (VII). Reduction of the 5‐formylpyrazoles (VI; R = II) with borohydride afforded the 5‐hydroxymethyl derivatives (VIII). The same 2,4‐dioxohexenoates (I) when treated with o‐phenylenediamine gave 2‐oxy‐quinoxalines (V; R = H, V; R = Me, V; R = Ph). The uv spectra data of these compounds are given.

Publisher's Statement

Copyright © 1973 Journal of Heterocyclic Chemistry. Publisher’s version of record: https://doi.org/10.1002/jhet.5570100104

Publication Title

Journal of Heterocyclic Chemistry

Recommended Citation

El Khadem, H., El‐Shafei, Z., Rateb, L., & Mokhtar, H. (1973). Synthesis of pyrazoles and oxyquinoxalines from 2,4‐dioxohexenoales. Journal of Heterocyclic Chemistry, 10(1), 15-19. http://doi.org/10.1002/jhet.5570100104
Retrieved from: https://digitalcommons.mtu.edu/michigantech-p/3731