Synthesis of Pyrrolidines and Pyrroles by Tandem Amination/Cyanation/Alkylation and Amination/Oxidation Sequences. Issue 26 (1st August 2014)

• Record Type: Journal Article
• Authors: Han, Junbin; Lu, Zhichao; Hammond, Gerald B.; Xu, Bo
• Is Part Of: European journal of organic chemistry. Issue 26(2014)
• Page Start: 5786
• Page End: 5792
• Publication Date: 2014-08-01
• Subjects: Synthetic methods -- Tandem reactions -- Reaction mechanisms -- Nitrogen heterocycles -- Amination; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201402748
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: Copper‐catalyzed three‐component tandem amination/cyanation/alkylation of the primary‐amine‐tethered alkynes1 gave α‐CN‐substituted pyrrolidines6 in good yields and regioselectivities. In addition, silver‐mediated tandem amination/oxidation of the secondary‐amine‐tethered alkynes7 produced functionalized pyrroles8 in good yields. All reactions were conducted in one pot without any protection/deprotection steps. Abstract : Copper‐catalyzed three‐component tandem amination/cyanation/alkylation of the primary‐amine‐tethered alkynes1 gives α‐CN‐substituted pyrrolidines6 in good yields and regioselectivities. In addition, silver‐mediated tandem amination/oxidation of the secondary‐amine‐tethered alkynes7 produces functionalized pyrroles8 in good yields.