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A One-Pot Synthesis-Functionalization Strategy for Streamlined Access to 2,5-Disubstituted 1,3,4-Oxadiazoles from Carboxylic Acids.

ABSTRACT: A one-pot 1,3,4-oxadiazole synthesis-arylation strategy for accessing 2,5-disubstituted 1,3,4-oxadiazoles, from carboxylic acids, N-isocyaniminotriphenylphosphorane (NIITP), and aryl iodides, is reported. The reaction sequence, featuring a second stage copper-catalyzed 1,3,4-oxadiazole arylation, was found to tolerate (hetero)aryl, alkyl, and alkenyl carboxylic acids, and (hetero)aryl iodide coupling partners. The effectiveness of the two-stage strategy was exemplified by the late-stage functionalization of five carboxylic acid-containing APIs, and an extension to the synthesis of aminated 1,3,4-oxadiazoles using N-benzoyloxy amine coupling partners was also demonstrated.

SUBMITTER: Matheau-Raven D

PROVIDER: S-EPMC9486941 | biostudies-literature | 2022 Sep

REPOSITORIES: biostudies-literature

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A One-Pot Synthesis-Functionalization Strategy for Streamlined Access to 2,5-Disubstituted 1,3,4-Oxadiazoles from Carboxylic Acids.

Matheau-Raven Daniel D Dixon Darren J DJ

The Journal of organic chemistry 20220902 18

A one-pot 1,3,4-oxadiazole synthesis-arylation strategy for accessing 2,5-disubstituted 1,3,4-oxadiazoles, from carboxylic acids, <i>N</i>-isocyaniminotriphenylphosphorane (NIITP), and aryl iodides, is reported. The reaction sequence, featuring a second stage copper-catalyzed 1,3,4-oxadiazole arylation, was found to tolerate (hetero)aryl, alkyl, and alkenyl carboxylic acids, and (hetero)aryl iodide coupling partners. The effectiveness of the two-stage strategy was exemplified by the late-stage f ...[more]

PMID: 36054913

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