BEHAVIOR OF IMIDAZOLE, 1,2,4-TRIAZOLE, AND BENZOTRIAZOLE IN AZA-MICHAEL REACTIONS WITH CROTONIC ACID

Document Type : Original Article

Authors

aScientific and Technological Center of Organic and Pharmaceutical Chemistry, NAS RA, Azatutyan 26 ave., Yerevan, 0014, Republic of Armenia

Abstract

To achieve high yields in chemical reactions, ensuring optimal conditions is crucial. This involves the complete use of starting materials and the absence of by-products. Aza-Michael reactions, particularly the additions of azoles to activated double bonds, significantly meet these criteria. The aza-Michael reaction plays a crucial role in the total synthesis of natural products and complex molecules, highlighting its practical utility in various industrial applications. Moreover, aza-Michael reaction is used to synthesize β-amino acids and β-amino ketones, which are valuable intermediates in the production of various biologically active compounds, including antibiotics and anticancer agents. It has been demonstrated that imidazole, its basicity plays a significant role with the reaction of crotonic acid leading to its quaternization with crotonic acid and the subsequent formation of imidazole cyanamate. For 1,2,4-triazole and benzotriazole, are attributed to the non-autocatalytic nature of the reactions and the reaction temperature.

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Articles in Press, Accepted Manuscript
Available Online from 06 October 2025
  • Receive Date: 21 November 2024
  • Revise Date: 04 February 2025
  • Accept Date: 04 October 2025