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Organocatalytic Triazole Formation, Followed by Oxidative Aromatization: Regioselective Metal‐Free Synthesis of Benzotriazoles
Author(s) -
Ramachary Dhevalapally B.,
Shashank Adluri B.
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201301412
Subject(s) - aromatization , regioselectivity , chemistry , cycloaddition , catalysis , pyrrolidine , amine gas treating , combinatorial chemistry , selectivity , aryl , organic chemistry , triazole , bicyclic molecule , alkyl
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.