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5-Formyltriazoles as Valuable Starting Materials for Unsymmetrically Substituted Bi-1,2,3-Triazoles.

ABSTRACT: Herein, we present the first synthetic methodologies toward non-symmetrical 5,5'-C, C-linked bi-1,2,3-triazoles starting from 5-formyl-1,2,3-triazole via two related pathways. In a first reaction, 5-formyl-1,2,3-triazole is successfully reacted with a variety of nitroalkanes and organic azides in a one-pot three-component fashion resulting in tetra-ortho-substituted bi-1,2,3-triazoles. In the second, closely related reaction, 5-formyl-1,2,3-triazole is initially converted with nitromethane to the corresponding nitroalkene, and then subsequently oxidatively cyclized with a number of organic azides toward 4-nitro substituted non-symmetrical tetra-ortho-substituted 5,5'-bi-1,2,3-triazoles. The scope of both reactions and furtherr post-functionalizations are examined, and the atropisomeric properties of the obtained bi-1,2,3-triazoles are evaluated.

SUBMITTER: Vroemans R

PROVIDER: S-EPMC7174647 | biostudies-literature | 2020

REPOSITORIES: biostudies-literature

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5-Formyltriazoles as Valuable Starting Materials for Unsymmetrically Substituted Bi-1,2,3-Triazoles.

Vroemans Robby R Horsten Tomas T Van Espen Maarten M Dehaen Wim W

Frontiers in chemistry 20200415

Herein, we present the first synthetic methodologies toward non-symmetrical 5,5'-C, C-linked bi-1,2,3-triazoles starting from 5-formyl-1,2,3-triazole via two related pathways. In a first reaction, 5-formyl-1,2,3-triazole is successfully reacted with a variety of nitroalkanes and organic azides in a one-pot three-component fashion resulting in tetra-ortho-substituted bi-1,2,3-triazoles. In the second, closely related reaction, 5-formyl-1,2,3-triazole is initially converted wi ...[more]

PMID: 32351938

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