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http://dx.doi.org/10.5012/bkcs.2012.33.1.39

Four-Component Synthesis of 2-(N,N-Dialkylamino)-2,4,6-Cycloheptatrien-1-One Derivatives from Tropolone, an Isocyanide, a Primary Amine and an Aldehyde via Ugi-Smiles Coupling Reaction  

Massoudi, Abdolhossain (Department of Chemistry, Payame Noor University)
Amini, Issa (Department of Chemistry, Payame Noor University)
Ramazani, Ali (Department of Chemistry, Zanjan Branch, Islamic Azad University)
Nasrabadi, Fatemeh Zeinali (Chemistry Department, Zanjan University)
Ahmadi, Yavar (Chemistry Department, Zanjan University)
Publication Information
Abstract
The use of Smiles rearrangement in Ugi-type couplings with tropolone allows very straightforward multicomponent formation of 2-(N,N-dialkylamino)-2,4,6-cycloheptatrien-1-one derivatives. The Ugi four-component reaction of isocyanides with tropolone (2-hydroxy-2,4,6-cycloheptatrien-1-one), primary amines and aldehydes proceeds smoothly and cleanly under mild conditions to afford 2-(N,N-dialkylamino)-2,4,6-cycloheptatrien-1-one derivatives in fairly good yields.
Keywords
Tropolone; Isocyanides; Primary amines; Aldehydes; Ugi-Smiles-type reaction;
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