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ChemInform Abstract: 5(4H)-Oxazolones. Part 11. Cycloaddition Reaction of Oxazolones and Muenchnones to Triphenylvinylphosphonium Salts as Synthetic Equivalents of Alkynes.

✍ Scribed by F. CLERICI; M. L. GELMI; P. TRIMARCO

Publisher: John Wiley and Sons
Year: 2010
Weight: 39 KB
Volume: 29
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199834141

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✦ Synopsis

5(4H)-Oxazolones. Part 11. Cycloaddition Reaction of Oxazolones and Muenchnones to Triphenylvinylphosphonium Salts as Synthetic Equivalents of Alkynes.

-The title reaction provides pyrroles with high regioselectivity. Interestingly, addition of the phosphonium salt (IV) to oxazolones like (I) does not yield the expected pyrrole carboxylic acids, whereas the addition to muenchnones [cf.(VII)] affords the desired products. The reaction of oxazolones with (IV) under mild conditions allows the isolation of pyrrolines of type (V) which easily eliminate the phosphonium group. -

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