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Sequencing [3+2]-cycloaddition and multicomponent reactions: A regioselective microwave-assisted synthesis of 1,4-disubstituted 1,2,3-triazoles using ionic liquid supported Cu(II) precatalysts in methanol

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Abstract Heterocyclic compounds with two to three nitrogen atoms play a pivotal role in the normal life cycle of a cell. Further the design and synthesis of a quality heterocyclic… Click to show full abstract

Abstract Heterocyclic compounds with two to three nitrogen atoms play a pivotal role in the normal life cycle of a cell. Further the design and synthesis of a quality heterocyclic compound library with N-atoms as new chemical probes active, is vital in drug discovery. In this context, an efficient one-pot multicomponent strategy for the synthesis of a mini library of 1,4-disubstituted 1,2,3-triazoles is described. This new multicomponent one-pot method features a combination of ionic liquid supported Cu(II) precatalysts in methanol catalyzed [3+2]-cycloaddition with microwave irradiation reactions. The synthetic manipulation involved the efficient reduction of ionic liquid supported Cu(II) catalyst by methanol followed by [3+2] cycloaddition with alkynes using in situ generated azides to obtain 1,2,3-triazoles regioselectively.

Keywords: ionic liquid; cycloaddition; disubstituted triazoles; liquid supported; synthesis

Journal Title: Tetrahedron Letters
Year Published: 2020

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