A new practical synthesis of 3-amino-substituted 5-aminopyrazoles and their tautomerism

Felicia Phei Lin Lim, Khai Ching Tan, Giuseppe Luna, Edward R.T. Tiekink, Anton V. Dolzhenko

    Research output: Contribution to journalArticleResearchpeer-review

    7 Citations (Scopus)

    Abstract

    It was found that 3-amino-substituted 5-aminopyrazoles could be effectively prepared via hydrolytic decarboxylation of the corresponding 3,5-diaminopyrazole-4-carboxylates under microwave irradiation. The reactions required short time (4 min) and were successfully reproduced in a larger scale and under conventional heating mimicking the microwave heating pattern. X-ray crystallography identified two different types of tautomers in crystals of related 5-aminopyrazoles with p-toluidyl and p-anisidyl moieties at the position 3, respectively.

    Original languageEnglish
    Pages (from-to)2314-2321
    Number of pages8
    JournalTetrahedron
    Volume75
    Issue number15
    DOIs
    Publication statusPublished - 12 Apr 2019

    Keywords

    • Decarboxylation
    • Hydrolysis
    • Microwave-assisted Synthesis
    • Pyrazole
    • Tautomerism

    Cite this