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- Title
Cycloaddition Reactions of Alkyl Cyclopropenecarboxylates Generated in situ with Nitrones: Construction of Substituted Pyrroles and 1,2-Oxazinanes.
- Authors
Hu, Junhao; Zhang, Min; Gong, Yuefa
- Abstract
A highly regioselective [3+2] cycloaddition reaction of nitrones 1 with alkyl 2-aroylcyclopropenecarboxylates generated in situ from alkyl 2-aroyl-1-chlorocyclopropanecarboxylates 2 under basic conditions is described. The reaction proceeded readily to afford ring-fused isoxazolidines 3 in moderate-to-high yields. The strained ring-fused cycloaddition products were selectively transformed into the corresponding polysubstituted pyrroles, for example, pyrrolizine derivatives, through N-O bond cleavage or 1,2-oxazinane derivatives through ring-opening by treatment with HCl ·pyridine in alcoholic solvents.
- Subjects
RING formation (Chemistry); ISOXAZOLIDINES; PYRROLES; ALKYL compounds; CHEMICAL derivatives; CHEMICAL reactions
- Publication
European Journal of Organic Chemistry, 2015, Vol 2015, Issue 9, p1970
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201403551