Barton–Zard reaction
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The Barton–Zard reaction is a route to pyrrole derivatives via the reaction of a nitroalkene with an α-isocyanide under basic conditions.[1] It is named after Derek Barton and Samir Zard who first reported it in 1985.[2]
Mechanism
The mechanism consists of five steps:
- Base catalyzed carbonyl enolization of the α-isocyanide.
- Michael-type addition between the α-isocyanidecarbonyl enolate and the nitroalkene.
- 5-endo-dig cyclization (see: Baldwin's rules).
- Base catalyzed elimination of the nitro group.
- Tautomerization leading to aromatisation.
Scope
The nitro compound may be aromatic rather than just an alkene.
References
- ISBN 9781118354421. pp.43-4
- .
- .
- PMID 14725469.
- doi:10.3987/REV-07-622 (inactive 2024-03-07).)
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: CS1 maint: DOI inactive as of March 2024 (link