ArticleChemical science2017
A convergent synthesis of 1,3,4-oxadiazoles from acyl hydrazides under semiaqueous conditions.
Article in Chemical science, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed, 45 citations in OpenAlex.
- Article
- Molecular Structure, Matrix-Isolation IR Spectrum and UV-Induced Transformations of 2-Amino-5-(4-Methoxyphenyl)-1,3,4-Oxadiazole.Molecules (Basel, Switzerland) · 2025Article
- Photoredox radical/polar crossover enables carbo-heterofunctionalization of alkenes: facile access to 1,3-difunctionalized nitro compounds.Chemical communications (Cambridge, England) · 2025Article
- An Electrosynthesis of 1,3,4-Oxadiazoles from N-Acyl Hydrazones.Chemistry (Weinheim an der Bergstrasse, Germany) · 2024Article
- Synthesis, Computational Studies, Antioxidant and Anti-Inflammatory Bio-Evaluation of 2,5-Disubstituted-1,3,4-Oxadiazole Derivatives.Pharmaceuticals (Basel, Switzerland) · 2023Article
- Preparation ofJournal of the American Chemical Society · 2022Article
- Enantioselective iodolactonization to prepare ε-lactone rings using hypervalent iodine.Chemical science · 2022Article
- Article
- Article
- The inverted ketene synthon: a double umpolung approach to enantioselective βChemical science · 2019Article
- 1,3,4-Oxadiazole and Heteroaromatic-Fused 1,2,4-Triazole Synthesis using Diverted Umpolung Amide Synthesis.Synthesis · 2017Article
Corrections and comments
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Authors and funding
2 authors at 1 institution in 2 countries.
Funding
Abstract
The 1,3,4-oxadiazole is an aromatic heterocycle valued for its low-lipophilicity in drug development. Substituents at the 2- and/or 5-positions can modulate the heterocycle's electronic and hydrogen bond-accepting capability, while exploiting its use as a carbonyl bioisostere. A new approach to 1,3,4-oxadiazoles is described wherein α-bromo nitroalkanes are coupled to acyl hydrazides to deliver the 2,5-disubstituted oxadiazole directly, avoiding a 1,2-diacyl hydrazide intermediate. Access to new building blocks of oxadiazole-substituted secondary amines is improved by leveraging chiral α-bromo nitroalkane or amino acid hydrazide substrates. The non-dehydrative conditions for oxadiazole synthesis are particularly notable, in contrast to alternatives reliant on highly oxophilic reagents to effect cyclization of unsymmetrical 1,2-diacyl hydrazides. The mild conditions are punctuated by the straightforward removal of co-products by a standard aqueous wash.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.