REARRANGEMENTS OF 1,2,4-OXADIAZOLE: ''ONE RING TO RULE THEM ALL''

Authors

  • Antonio Palumbo Piccionello Università degli Studi di Palermo
  • Andrea Pace Università degli Studi di Palermo
  • Silvestre Buscemi Università degli Studi di Palermo

DOI:

https://doi.org/10.1007/4036

Keywords:

1, 2, 4-oxadiazole, ANRORC, Boulton–Katritzky rearrangement, heterocyclic rearrangement, photochemistry

Abstract

1,2,4-Oxadiazoles are heterocycles characterized by low aromaticity and the presence of a weak O–N bond and are widely studied due to their tendency to rearrange into more stable heterocyclic compounds. This review covers literature from the last fifteen years, highlighting the general features of 1,2,4-oxadiazoles and their applications. Regarding the reactivity, the development of classical reactions (thermal and photochemical rearrangements) is presented in terms of synthetic utility and mechanistic insight. Among the relevant rearrangement reactions, the Boulton–Katritzky Rearrangement (BKR), Migration – Nucleophilic Attack – Cyclization (MNAC), and Addition of the Nucleophile, Ring Opening, and Ring Closure (ANRORC) reactions are discussed, together with recent noteworthy syntheses and applications of the 1,2,4-oxadiazole ring.

Author Biographies

Antonio Palumbo Piccionello, Università degli Studi di Palermo

Dipartimento di Scienze e Tecnologie Biologiche Chimiche e Farmaceutiche-STEBICEF

Assistant Professor

Andrea Pace, Università degli Studi di Palermo

Silvestre Buscemi, Università degli Studi di Palermo

Published

2017-11-03