Barton–Zard reaction
From Wikipedia, the free encyclopedia
The Barton-Zard reaction is a route to pyrrole derivatives via the reaction of a nitroalkene with an α-isocyanoacetate under basic conditions.[1] It is named after Derek Barton and Samir Zard who first reported it in 1990.
Mechanism
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.[1]
References
- ↑ 1.0 1.1 Jie Jack Li (2013). Heterocyclic Chemistry in Drug Discovery. New York: Wiley. ISBN 9781118354421. pp.43-4
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