title: The divergent synthesis of nitrogen heterocycles by rhodium(II)-catalyzed cycloadditions of 1-sulfonyl 1,2,3-triazoles with 1,3-dienes.
abstract: The first rhodium(II)-catalyzed aza-[4+3] cycloadditions of 1-sulfonyl 1,2,3-triazoles with 1,3-dienes have been developed, and enable the efficient synthesis of highly functionalized 2,5-dihydroazepines from readily available precursors. In some cases, the reaction pathway could divert to formal aza-[3+2] cycloadditions, thus leading to 2,3-dihydropyrroles. In this context, the titled reaction represents a capable tool for the divergent synthesis of two types of synthetically valuable aza-heterocycles from common rhodium(II) iminocarbene intermediates.
authors.affiliation: The Comprehensive AIDS Research Center, Department of Pharmacology & Pharmaceutical Sciences, School of Medicine, Tsinghua University, Beijing 100084 (China).
authors.forename: Hai
authors.initials: H
authors.lastname: Shang
authors.forename: Yuanhao
authors.initials: Y
authors.lastname: Wang
authors.forename: Yu
authors.initials: Y
authors.lastname: Tian
authors.forename: Juan
authors.initials: J
authors.lastname: Feng
authors.forename: Yefeng
authors.initials: Y
authors.lastname: Tang
mesh_terms: D000466:Alkadienes / Q000737:chemistry*; D001381:Azepines / Q000737:chemistry; D002384:Catalysis; D061565:Cycloaddition Reaction; D006571:Heterocyclic Compounds / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives / Q000737:chemistry; D009584:Nitrogen / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry*; D014230:Triazoles / Q000737:chemistry*
chemical_list: D000466:Alkadienes; D001381:Azepines; D006571:Heterocyclic Compounds; D014230:Triazoles; C030011:carbene; D012238:Rhodium; D009584:Nitrogen; D008697:Methane
keywords: carbenes; cycloaddition; nitrogen heterocycles; rhodium; synthetic methods