199276-69-2Relevant articles and documents
Atom-Economical Cross-Coupling of Internal and Terminal Alkynes to Access 1,3-Enynes
Liu, Mingyu,Tang, Tianhua,Apolinar, Omar,Matsuura, Rei,Busacca, Carl A.,Qu, Bo,Fandrick, Daniel R.,Zatolochnaya, Olga V.,Senanayake, Chris H.,Song, Jinhua J.,Engle, Keary M.
, p. 3881 - 3888 (2021/04/06)
Selective carbon-carbon (C-C) bond formation in chemical synthesis generally requires prefunctionalized building blocks. However, the requisite prefunctionalization steps undermine the overall efficiency of synthetic sequences that rely on such reactions, which is particularly problematic in large-scale applications, such as in the commercial production of pharmaceuticals. Herein, we describe a selective and catalytic method for synthesizing 1,3-enynes without prefunctionalized building blocks. In this transformation several classes of unactivated internal acceptor alkynes can be coupled with terminal donor alkynes to deliver 1,3-enynes in a highly regio- and stereoselective manner. The scope of compatible acceptor alkynes includes propargyl alcohols, (homo)propargyl amine derivatives, and (homo)propargyl carboxamides. This method is facilitated by a tailored P,N-ligand that enables regioselective addition and suppresses secondary E/Z-isomerization of the product. The reaction is scalable and can operate effectively with as low as 0.5 mol % catalyst loading. The products are versatile intermediates that can participate in various downstream transformations. We also present preliminary mechanistic experiments that are consistent with a redox-neutral Pd(II) catalytic cycle.
The acid-mediated intramolecular 1,3-dipolar cycloaddition of derived 2-nitro-1,1-ethenediamines for the synthesis of novel fused bicyclic isoxazoles
Page, Lee W.,Bailey, Matthew,Beswick, Paul J.,Frydrych, Simon,Gleave, Robert J.
scheme or table, p. 3388 - 3391 (2010/09/05)
The discovery of a novel synthesis of new fused bicyclic isoxazoles, for example, N-methyl-3-phenyl-5,6-dihydro-4H-isoxazolo[3,4-c]azepin-8-amine (2a), N-methyl-3-phenyl-4,5-dihydroisoxazolo[3,4-c]pyridin-7-amine (2b) and N-methyl-3-phenyl-4H-pyrrolo[3,4-
Facile synthesis of medium-sized cyclic amines based on Friedel-Crafts reaction via iminium cation by use of acetylene dicobalt complex
Mizukami, Megumi,Saito, Hiroshi,Higuchi, Toshio,Imai, Masanori,Bando, Hideo,Kawahara, Norio,Nagumo, Shinji
, p. 7228 - 7231 (2008/03/11)
An intramolecular Friedel-Crafts reaction of N-methoxymethyl sulfoneamides 3e-j containing an acetylene dicobalt moiety was found to proceed smoothly to afford eight- and nine-membered cyclic amines 4e-j in high yields.