Work

Metal-Free Synthesis of Polysubstituted Triazoloquinoxalines Using Alkynols as the Key Building Blocks

Year: 2024

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide o -Phenylenediamines, o -nitroanilines, and Boc- o -phenylenediamines were converted to N -Ts/Ns- o -phenylenediamines, followed by Mitsunobu alkylation with prop-2-yn-1-ols. After one-pot azidation, the resulting intermediates underwent Huisgen cycloaddition, which yielded Ts/Ns-dihydrotriazoloquinoxalines. Cleavage of the arylsulfonyl moiety provided (dihydro)triazoloquinoxalines with the possibility of modifying the N 5 position. The application of but-3-yn-1-ols and pent-4-yn-1-ols allowed the preparation of benzotriazolodiazepines and benzotriazolodiazocines. The developed protocols enable the preparation of diversely substituted products from readily available starting materials under mild and metal-free conditions.

Source: ACS Omega

DOI: 10.1021/acsomega.4c03979

Authors: Berenika Masaryk, Miroslav Soural

Institution: Palacký University Olomouc

Language: English

Topic: Click Chemistry and Applications

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $1,935

Funders: Grantová Agentura České Republiky, Univerzita Palackého v Olomouci