Abstract
Cyclic amines such as pyrrolidine and 1,2,3,4-tetrahydroisoquinoline undergo redox-annulations with α,β-unsaturated aldehydes and ketones. Carboxylic acid promoted generation of a conjugated azomethine ylide is followed by 6π-electrocylization, and, in some cases, tautomerization. The resulting ring-fused pyrrolines are readily oxidized to the corresponding pyrroles or reduced to pyrrolidines.
Publication types
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Research Support, N.I.H., Extramural
MeSH terms
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Aldehydes / chemistry*
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Amines / chemical synthesis
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Amines / chemistry*
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Azo Compounds / chemistry
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Carbon / chemistry
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Carboxylic Acids / chemistry
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Crystallography, X-Ray
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Cyclization
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Hydrogen / chemistry
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Isoquinolines / chemical synthesis
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Isoquinolines / chemistry
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Ketones / chemistry*
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Molecular Conformation
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Oxidation-Reduction
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Pyrrolidines / chemical synthesis
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Pyrrolidines / chemistry
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Thiosemicarbazones / chemistry
Substances
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Aldehydes
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Amines
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Azo Compounds
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Carboxylic Acids
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Isoquinolines
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Ketones
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Pyrrolidines
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Thiosemicarbazones
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azomethine
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Carbon
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Hydrogen
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isoquinoline
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pyrrolidine