In Situ-Generated\nFormamidine as a Carbon/Nitrogen\nSource for Enaminone Formation: One-Pot Synthesis of Functionalized\n4‑Acyl-1,2,3-triazoles

<i>N</i>,<i>N</i>-Dimethylformamide\nwas reacted\nwith hexamethyldisilazane to generate an <i>N</i>,<i>N</i>-dimethylformimidamide intermediate; thereafter, a reaction\nwith acetophenones/β-diketones was induced to form enaminones.\nThe one-pot synthetic protocol described in this paper can be applied\nto synthesize 1,4-disubstituted 1,2,3-triazoles and 1,4,5-trisubstituted\n1,2,3-triazoles, in which organic azides are used as substrates under\noptimized conditions. Furthermore, this protocol uses readily available\nmaterials, is nearly free of solvent, can be applied to gram-scale\noperations, and leads to the formation of structurally diverse products\nwith favorable yields.

Publication Details

Journal
Figshare
Published
2024-08-19
DOI
https://doi.org/10.1021/acs.joc.4c01054.s001
Primary Topic
Synthesis and Characterization of Pyrroles
Type
article
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article

In Situ-Generated\nFormamidine as a Carbon/Nitrogen\nSource for Enaminone Formation: One-Pot Synthesis of Functionalized\n4‑Acyl-1,2,3-triazoles

Figshare
Synthesis and Characterization of Pyrroles
article

In Situ-Generated\nFormamidine as a Carbon/Nitrogen\nSource for Enaminone Formation: One-Pot Synthesis of Functionalized\n4‑Acyl-1,2,3-triazoles

article en

Abstract

<i>N</i>,<i>N</i>-Dimethylformamide\nwas reacted\nwith hexamethyldisilazane to generate an <i>N</i>,<i>N</i>-dimethylformimidamide intermediate; thereafter, a reaction\nwith acetophenones/β-diketones was induced to form enaminones.\nThe one-pot synthetic protocol described in this paper can be applied\nto synthesize 1,4-disubstituted 1,2,3-triazoles and 1,4,5-trisubstituted\n1,2,3-triazoles, in which organic azides are used as substrates under\noptimized conditions. Furthermore, this protocol uses readily available\nmaterials, is nearly free of solvent, can be applied to gram-scale\noperations, and leads to the formation of structurally diverse products\nwith favorable yields.

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Openalex Percentile: Top 80%
Synthesis and Characterization of Pyrroles
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