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Green alternatives for the synthesis of tetrazolic acids

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Chemistry of Heterocyclic Compounds Aims and scope

Tetrazolic acids (5-substituted 1H-tetrazoles) are of great interest due to their bioisosterism with carboxylic acids, which accounts for plethora of their pharmacological activities and medicinal applications. Many reports deal with the synthesis of tetrazolic acids using different reactions and synthetic methods. This review intends to summarize most of the green approaches available for obtaining these heterocycles. The starting point in the discussion is the application of multicomponent reactions for the construction of structurally diverse products. However, the most commonly used reaction to afford tetrazolic acids is 1,3-dipolar cycloaddition of azide ion to nitriles. Hence, transition from homogeneous catalysis employed in the early examples of this method to heterogeneous catalysis applying recoverable reagents is highlighted. Similarly, the quest for eco-friendly reaction medium is thoroughly described stressing the use of novel systems like ionic liquids and deep eutectic solvents, reactions in aqueous medium, and solvent-free conditions. Further discussion emphasizes the advantages offered by solid-phase synthesis and nonconventional microwave-assisted reactions. Finally, several examples of successful combinations of different green tactics in a same experimental procedure are presented. Thereby, this article aims to provide the main trends for achieving synthesis of tetrazolic acids using environmentally benign procedures reported in the literature while giving perspectives of possible future advances in this topic.

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Gerardo M. Ojeda-Carralero acknowledges VLIR-UOS for the financial support in frame of Flemish-Cuba cooperation project (CU2018TEA458A101).

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Authors and Affiliations

  1. Center for Natural Product Research, Faculty of Chemistry, University of Havana, Zapata y G Ave, 10400, Havana, Cuba

    Gerardo M. Ojeda-Carralero & Arianna Valdés-Palacios

  2. Laboratory for Organic and Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, University of Leuven (KU Leuven), Celestijnenlaan 200F, B-3001, Leuven, Belgium

    Gerardo M. Ojeda-Carralero

  3. Laboratory of Organic Synthesis, Faculty of Chemistry, University of Havana, Zapata y G Ave, 10400, Havana, Cuba

    Julieta Coro

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  1. Gerardo M. Ojeda-Carralero
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  2. Julieta Coro
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Correspondence to Gerardo M. Ojeda-Carralero or Julieta Coro.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(4), 408–421

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Ojeda-Carralero, G.M., Coro, J. & Valdés-Palacios, A. Green alternatives for the synthesis of tetrazolic acids. Chem Heterocycl Comp 56, 408–421 (2020). https://doi.org/10.1007/s10593-020-02676-7

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