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  • Organocatalytic triazole formation, followed by oxidative aromatization: regioselective metal-free synthesis of benzotriazoles.

Organocatalytic triazole formation, followed by oxidative aromatization: regioselective metal-free synthesis of benzotriazoles.

Chemistry (Weinheim an der Bergstrasse, Germany) (2013-09-17)
Dhevalapally B Ramachary, Adluri B Shashank
ABSTRACT

Herein we report on our studies on the sequential one-pot combinations of amine-catalyzed multicomponent reactions (MCRs). We have developed the copper-free synthesis of functionalized bicyclic N-aryl-1,2,3-triazole and N-arylbenzotriazole products 4 and 5 from the simple unmodified starting materials through [3+2]-cycloaddition ([3+2]-CA) and oxidative aromatization reactions in one pot under amine catalysis. The sequential one-pot reaction proceeds in good yields with high selectivity by using pyrrolidine as the catalyst from the simple unmodified substrates of enones, aryl azides, and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). Furthermore, we have demonstrated the medicinal applications of products 4 and 5 through simple organic reactions.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
2,3-Dichloro-5,6-dicyano-p-benzoquinone, 98%
Sigma-Aldrich
Pyrrolidine, ≥99.5%, purified by redistillation
Sigma-Aldrich
Pyrrolidine, ≥99.0%
Sigma-Aldrich
Pyrrolidine, FG
Sigma-Aldrich
Pyrrolidine, 99%