5(4H)-oxazolones. Part XIII. A new synthesis of 4-ylidene-5(4H)-oxazolones by the Stille reaction
โ Scribed by Egle Maria Beccalli; Francesca Clerici; Maria Luisa Gelmi
- Publisher
- Elsevier Science
- Year
- 1999
- Tongue
- French
- Weight
- 296 KB
- Volume
- 55
- Category
- Article
- ISSN
- 0040-4020
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โฆ Synopsis
4--Chloromethyiene-2-ph~yl-5(4H)-oxazolone 1 was used as the starting material for the preparation of a series cf 4-ylideneoxazolones 3 by the Stille reaction. When compound 1 was reacted with organostannanes 2 in the presence of the palladium caUdyst, OXaZ~OB~ 3 w~re oblailgd in good yields in mild reaction conditions. @
๐ SIMILAR VOLUMES
A bstract:~(Z-Oxa-alkylidene)-~4~~x~olones (azlactones) 1 can be transformed in acidic conditions (anhydrous HBrlCHC13) into 5-alkylidene-3-benzoyI~~2(S~-furawnes 2 which have Z configuration at the exocyclic double bond. The same reaction conducted in acetic acid as solvent gives. besides the alkyh
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