• Recent developments in the chemistry of perhydroindoles and perhydrocinnolines

    • Fulltext

       

        Click here to view fulltext PDF


      Permanent link:
      https://www.ias.ac.in/article/fulltext/jcsc/093/06/1079-1097

    • Keywords

       

      Perhydroindoles; perhydrocinnolines; antifertility; cns depressants; analgesics; azamorphinans; aromatization; antiinflammatory activities

    • Abstract

       

      Recent synthetic routes to the tetrahydro, hexahydro and octahydro derivatives of indoles are reviewed. An interesting one is the formation of 3-amino-4-oxo-4,5,6,7-tetrahydroindoles in the reaction of 2-phenacyl cyclohexane-l,3-diones with 1,1-disubstituted hydrazines. Antifertility, cns depressant and antiinflammatory activities have been encountered for perhydroindoles besides other biological activities. Hexahydrocinnolines are obtained from the reaction of 2-phenacyl (acetonyl) cyclohexanones and cyclohexane-1,3-diones with hydrazines, while octahydrocinnolines are formed from cyclohexanone-2-acetic acids and hydrazines in two steps. 5-oxo-5,6,7,8-hexahydrocinnolines and their oximes undergo anomalous and interesting aromatisation reactions. Some hexahydrocinnolines are cns depressants while octahydrocinnolines are analgesics. More importantly, they are precursors for interesting azamorphinans.

    • Author Affiliations

       

      K Nagarajan1

      1. Hindustan CIBA-GEIGY Limited, Research Centre Goregaon East, Bombay - 400 063, India
    • Dates

       
  • Journal of Chemical Sciences | News

© 2021-2022 Indian Academy of Sciences, Bengaluru.