An Azomethine Ylide Approach to Complex Alkaloid-like Heterocycles

The nitrone above is readily available via the intramolecular aza Diels−Alder reaction of an amino acid derived triene in acetic acid. Subsequent treatment of the nitrone in refluxing toluene with substituted actetylenes produced the pictured pyrrole. At lower temperatures a 2,3-dihydroisoxazole, wh...

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Bibliographic Details
Published in:Journal of organic chemistry 2007-04, Vol.72 (8), p.3097-3099
Main Authors: Murray, William V, Francois, David, Maden, Amy, Turchi, Ignatius
Format: Article
Language:English
Subjects:
Alkaloids - chemistry
Azo Compounds - chemistry
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Heterocyclic Compounds, 4 or More Rings - chemistry
Molecular Structure
Organic chemistry
Preparations and properties
Pyrroles - chemical synthesis
Pyrroles - chemistry
Thiosemicarbazones - chemistry
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Description
Summary:The nitrone above is readily available via the intramolecular aza Diels−Alder reaction of an amino acid derived triene in acetic acid. Subsequent treatment of the nitrone in refluxing toluene with substituted actetylenes produced the pictured pyrrole. At lower temperatures a 2,3-dihydroisoxazole, which is the product of a 3 + 2 dipolar cycloaddition, is produced. Upon heating in refluxing toluene the 2,3-dihydroisoxazole is converted to the pyrrole.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo062579a