Expeditious, Metal-Free, Domino, Regioselective Synthesis of Highly Substituted 2-Carbonyl- and 2-Phosphorylfurans by Formal [3+2] Cycloaddition - Aix-Marseille Université Access content directly
Journal Articles European Journal of Organic Chemistry Year : 2012

Expeditious, Metal-Free, Domino, Regioselective Synthesis of Highly Substituted 2-Carbonyl- and 2-Phosphorylfurans by Formal [3+2] Cycloaddition

Wilfried Raimondi
  • Function : Author
Thierry Constantieux
  • Function : Author
Damien Bonne
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Jean Rodriguez
  • Function : Author
  • PersonId : 921781

Abstract

-Functionalized furans are very easily synthesized by exploiting the dual nucleophilic character of 1,2-dicarbonyls and the dual electrophilic properties of (2-chloro-2-nitroethenyl)benzenes in a one-pot, formal [3+2] cycloaddition. Using a base (DBU), the desired trisubstituted heterocycles were formed rapidly (10-30 min) in good to excellent yields (51-92 %), and this versatile, metal-free methodology was applied to the synthesis of 2-acyl- and 2-carboalkoxyfurans and furan-2-carboxamides. Additionally, by using 2-ketophosphonate derivatives as dinucleophiles, the corresponding 2-phosphorylfurans were formed in good yields (53-74 %).

Dates and versions

hal-00747378 , version 1 (31-10-2012)

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Cite

Wilfried Raimondi, Daniel Dauzonne, Thierry Constantieux, Damien Bonne, Jean Rodriguez. Expeditious, Metal-Free, Domino, Regioselective Synthesis of Highly Substituted 2-Carbonyl- and 2-Phosphorylfurans by Formal [3+2] Cycloaddition. European Journal of Organic Chemistry, 2012, pp.6119-6123. ⟨10.1002/ejoc.201201192⟩. ⟨hal-00747378⟩
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