Review of Synthesis of 1,3,4-Oxadiazole Derivatives

  title={Review of Synthesis of 1,3,4-Oxadiazole Derivatives},
  author={Kinjal D. Patel and Shraddha M. Prajapati and Shyamali N. Panchal and Hitesh D. Patel},
  journal={Synthetic Communications},
  pages={1859 - 1875}
Abstract 1,3,4-Oxadiazole nucleus shows a broad spectrum of pharmaceutical applications. Thus, in recent years scientists have developed various new methods for the synthesis of its derivatives. Here we give a review of recent developments in the synthesis over the past decade (2004–2013). GRAPHICAL ABSTRACT 
A convergent synthesis of 1,3,4-oxadiazoles from acyl hydrazides under semiaqueous conditions† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c7sc00195a Click here for additional data file.
An innovative new synthesis approach to disubstituted 1,3,4-oxadiazoles is described, inspired by Umpolung Amide Synthesis (UmAS).
Design, synthesis and molecular docking studies of some 1-(5-(2-fluoro-5-(trifluoromethoxy)phenyl)-1,2,4-oxadiazol-3-yl)piperazine derivatives as potential anti-inflammatory agents.
The facile synthesis of a series of 3,5-substituted-1,2,4-oxadiazole derivatives in good to excellent yields is reported, and some of the compounds exhibited profound activity profile when compared to the standard drug.
UV‐Induced 1,3,4‐Oxadiazole Formation from 5‐Substituted Tetrazoles and Carboxylic Acids in Flow
A range of 1,3,4‐oxadiazoles have been synthesized using a UV‐B activated flow approach starting from carboxylic acids and 5‐substituted tetrazoles, demonstrating comparable efficiency and versatility, with a diverse substrate scope, including the incorporation of highly substituted amino acids.
Mechanochemical Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazoles Mediated by PPh3-TCCA
Mechanochemical synthesis of 2,5-disubstituted 1,3,4-oxadiazoles was developed as an environmentally benign alternative to conventional solvent-based methods. In the presence of triphenylphosphine
Sequential Multicomponent Synthesis of 2-(Imidazo[1,5-α]pyridin-1-yl)-1,3,4-Oxadiazoles
A 21 membered library of 2-(imidazo[1,5-alpha]pyridine-1-yl)-1,3,4-oxadiazoles is synthesized in an unprecedented short sequence starting from an Ugi tetrazole reaction with a cleavable isocyanide
A Three-Component Ugi-Type Reaction of N-Carbamoyl Imines Enables a Broad Scope Primary α-Amino 1,3,4-Oxadiazole Synthesis.
A general synthesis of N-protected primary α-amino 1,3,4-oxadiazoles, from N-carbamoyl imines, N-isocyaniminotriphenylphosphorane (NIITP), and carboxylic acids, is described. Featuring an isocyanide
Application of NMI-TfCl-mediated amide bond formation in the synthesis of biologically relevant oxadiazole derivatives employing less basic (hetero)aryl amines
A modified methodology for the synthesis of some oxadiazoles linked to amides under mild conditions using NMI-TfCl has been found to be effective and tolerant for the amide bond formation reaction of a series of electronically deactivated and sterically challenging amines.
Application of N-Acylbenzotriazoles in the Synthesis of 5-Substituted 2-Ethoxy-1,3,4-oxadiazoles as Building Blocks toward 3,5-Disubstituted 1,3,4-Oxadiazol-2(3H)-ones.
5-Substituted-2-ethoxy-1,3,4-oxadiazoles were conveniently prepared through a one-pot sequential N-acylation/dehydrative cyclization between ethyl carbazate and N-acylbenzotriazoles in the presence
1,3,4-Oxadiazole and Heteroaromatic-Fused 1,2,4-Triazole Synthesis using Diverted Umpolung Amide Synthesis.
Diversion to 1,2,4-triazole products is described, a behavior hypothesized to also result from an analogous tetrahedral intermediate, but one formed from heteroaromatic hydrazine acceptors.


Efficient phosphonium-mediated synthesis of 2-amino-1,3,4-oxadiazoles.
This approach provides convenient access to N,N-disubstituted 2-amino-1,3,4-oxadiazoles, which are difficult to prepare using existing synthetic strategies.
Synthesis of 1,3,4-oxadiazoles from 1,2-diacylhydrazines using [Et2NSF2]BF4 as a practical cyclodehydration agent.
Various functionalized 1,3,4-oxadiazoles were synthesized and it was found that the use of acetic acid as an additive generally improved the yields.