title: Organocatalytic triazole formation, followed by oxidative aromatization: regioselective metal-free synthesis of benzotriazoles.
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.
authors.affiliation: Catalysis Laboratory, School of Chemistry, University of Hyderabad, Hyderabad-500 046 (India), Fax: (+91) 40-23012460. ramsc@uohyd.ernet.in, ramchary.db@gmail.com.
authors.forename: Dhevalapally B
authors.initials: DB
authors.lastname: Ramachary
authors.forename: Adluri B
authors.initials: AB
authors.lastname: Shashank
mesh_terms: D000588:Amines / Q000737:chemistry*; D001386:Azides / Q000138:chemical synthesis; D016227:Benzoquinones / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D057930:Click Chemistry; D003300:Copper; D061565:Cycloaddition Reaction; D011759:Pyrrolidines / Q000737:chemistry*; D013237:Stereoisomerism; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000588:Amines; D001386:Azides; D016227:Benzoquinones; D011759:Pyrrolidines; D014230:Triazoles; C000928:dichlorodicyanobenzoquinone; D003300:Copper; C012771:benzotriazole; C032519:pyrrolidine
keywords: amines; azides; click chemistry; cycloaddition; multicomponent reactions; triazoles