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Smiles Rearrangements in Ugi- and Passerini-Type Couplings: New Multicomponent Access to O- and N-Arylamides

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Laurent El Kaïm,* Marie Gizolme, Laurence Grimaud,* and Julie Oble;

Laboratoire Chimie et procédés, UMR 7652, Ecole Nationale Supérieure de Techniques Avancées, 32 Bd Victor, Paris 75015, France

J. Org. Chem., 2007, 72 (11), pp 4169–4180

DOI: 10.1021/jo070202e

Publication Date (Web): April 25, 2007

Section:

Benzene, Its Derivatives, and Condensed Benzenoid Compounds

Abstract

The use of Smiles rearrangement in Ugi- and Passerini-type couplings with electron-deficient phenols allows very straightforward multicomponent formation of O-aryl- and N-arylamides. Best yields were observed with the highly activated o- and p-nitrophenols, salicylic derivatives giving adducts in lower yields. The scope of these new reactions is further increased by the successful couplings of heterocyclic phenols such as hydroxypyridines and hydroxypyrimidines.

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This article has been cited by 12 ACS Journal articles (5 most recent appear below).

Challenging 50 Years of Established Views on Ugi Reaction: A Theoretical Approach
Nicolas Chéron, Romain Ramozzi, Laurent El Kaïm, Laurence Grimaud, and Paul Fleurat-Lessard
The Journal of Organic Chemistry2012 77 (3), 1361-1366
- Challenging 50 Years of Established Views on Ugi Reaction: A Theoretical Approach
  Nicolas Chéron, Romain Ramozzi, Laurent El Kaïm, Laurence Grimaud, and Paul Fleurat-Lessard
  The Journal of Organic Chemistry2012 77 (3), 1361-1366
  The Ugi reaction is one of the most famous multicomponent couplings, and its efficiency is still explained by the original mechanism suggested by Ugi in the 60s. This article aims to present a thorough theoretical study of this reaction. It describes how ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Ugi–Smiles Couplings of 4-Substituted Pyridine Derivatives: A Fast Access to Chloroquine Analogues
Laurent El Kaïm, Laurence Grimaud, and Patil Pravin
Organic Letters2012 14 (2), 476-478
- Ugi–Smiles Couplings of 4-Substituted Pyridine Derivatives: A Fast Access to Chloroquine Analogues
  Laurent El Kaïm, Laurence Grimaud, and Patil Pravin
  Organic Letters2012 14 (2), 476-478
  4-Hydroxy and mercapto pyridines were successfully tested in Ugi–Smiles couplings. Such multicomponent reactions applied to quinoline derivatives afford a very convenient and short synthesis of antimalarial analogues.
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Multicomponent Synthesis of Fused Benzimidazolopiperazines
Laurent El Kaïm, Laurence Grimaud, and Srinivas Reddy Purumandla
The Journal of Organic Chemistry2011 Article ASAP
- Multicomponent Synthesis of Fused Benzimidazolopiperazines
  Laurent El Kaïm, Laurence Grimaud, and Srinivas Reddy Purumandla
  The Journal of Organic Chemistry2011 Article ASAP
  We present a novel protocol for the efficient synthesis of fused benzimidazolo piperazines starting from a four-component Ugi–Smiles reaction and a subsequent three-step cascade involving an acid-catalyzed cyclization, an intramolecular reductive ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Smiles Cascades toward Heterocyclic Scaffolds
Laurent El Kaim, Laurence Grimaud, Xavier F. Le Goff, and Aurélie Schiltz
Organic Letters2011 13 (3), 534-536
- Smiles Cascades toward Heterocyclic Scaffolds
  Laurent El Kaim, Laurence Grimaud, Xavier F. Le Goff, and Aurélie Schiltz
  Organic Letters2011 13 (3), 534-536
  Two different Smiles rearrangements can be combined to afford a multicomponent formation of isoquinolinones and isoindolinones from nitro methyl salicylate. After a Ugi−Smiles four-component coupling, the base-triggered cyclization of the resulting ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Direct Construction of Imino-pyrrolidine-thione Scaffold via Isocyanide-Based Multicomponent Reaction
Xu Zhu, Xiao-Ping Xu, Chang Sun, Hai-Ying Wang, Kai Zhao, and Shun-Jun Ji
Journal of Combinatorial Chemistry2010 12 (6), 822-828
- Direct Construction of Imino-pyrrolidine-thione Scaffold via Isocyanide-Based Multicomponent Reaction
  Xu Zhu, Xiao-Ping Xu, Chang Sun, Hai-Ying Wang, Kai Zhao, and Shun-Jun Ji
  Journal of Combinatorial Chemistry2010 12 (6), 822-828
  A novel and efficient method has been developed for the direct construction of imino-pyrrolidine-thione scaffold via the coupling of isocyanides, heterocyclic thiols, and gem-dicyano olefins. Smiles rearrangement followed by intramolecular cyclization ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links