Copper-Catalyzed Transformation of Hydrazones into Halogenated Azabutadienes, Versatile Building Blocks for Organic Synthesis

A one-step copper-catalyzed reaction of aldehyde-derived N-substituted hydrazones with CCl4 resulted in efficient synthesis of 4,4-dichloro-1,2-diazabuta-1,3-dienes. It was proven that this C-C bond-forming cascade reaction operates via an addition of trichloromethyl radical to the C=N bond of hydrazone followed by a base-induced elimination of HCl. The reaction was found to be very general, as diverse hydrazones possessing various aromatic groups at N-site, as well as aromatic, aliphatic, and heterocyclic substituents at C-site, are capable partners for coupling with a wide range of polyhalogenated compounds (CCl3Br, CBr4, CCl3CN, CCl3COOEt, CCl3CF3, CBr3CF3) to produce a family of functionalized 1,2-diazabuta-1,3-dienes. It was demonstrated that the prepared heterodienes are highly versatile building blocks for straightforward assembly of various valuable acyclic and heterocyclic molecules. © 2016 American Chemical Society.

Authors
Nenajdenko V.G.1 , Shastin A.V.1, 2 , Gorbachev V.M.1 , Shorunov S.V.1 , Muzalevskiy V.M.1 , Lukianova A.I.1 , Dorovatovskii P.V.3 , Khrustalev V.N. 4
Journal
Publisher
American Chemical Society
Number of issue
1
Language
English
Pages
205-209
Status
Published
Volume
7
Year
2017
Organizations
  • 1 Department of Chemistry, Lomonosov Moscow State University, Moscow, 119899, Russian Federation
  • 2 Institute of Problems of Chemical Physics, Russian Academy of Sciences, Chernogolovka, 142432, Russian Federation
  • 3 National Research Center, Kurchatov Institute, Moscow, 123182, Russian Federation
  • 4 Peoples' Friendship University of Russia, Moscow, 117198, Russian Federation
Keywords
copper; heterodiene; homogeneous catalysis; hydrazones; reaction mechanisms
Date of creation
19.10.2018
Date of change
19.10.2018
Short link
https://repository.rudn.ru/en/records/article/record/5650/