The Barton-Zard reaction is a route to pyrrole derivatives via the reaction of a nitroalkene with an α-isocyanoacetate under basic conditions. It is named after Derek Barton and Samir Zard who first reported it in 1990.
The mechanism consists of five steps:
- Base catalyzed carbonyl enolizaton of the α-isocyanide.
- Michael-type addition between the α-isocyanide carbonyl enolate and the nitroalkene.
- 5-endo-dig cyclization.
- Base catalyzed elimination of the nitro group.
- 1,5-sigmatropic rearrangement leading to aromatisation.
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