ISSN:
0075-4617
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
Dakin West Reaction, IV1). - Reaction of α-Amino Dicarboxylic Acids with Carboxylic Acid Anhydrides2)The Dakin West reaction of N-acylaspartic anhydrides yields furo[3,2-d]oxazoles 5 and 14, 2(5H)-furanones 8 or 6H-1,3-oxazin-6-ones 9, depending on the reaction conditions. N-Thiobenzoylaspartic acid is converted into 6H-1,3-thiazin-6-one (12) by treatment with acetic anhydride and 3-picoline. Glutamic acid gives 1,5-diacetyl-2-pyrrolidone (22) in high yield on warming with acetic anhydride and 4-(dimethylamino)pyridine. Possible mechanisms for the formation of the different products are discussed.
Notes:
N-Acylasparaginsäureanhydride liefern bei der Dakin-West-Reaktion je nach den Reaktionsbedingungen Furo[3,2-d]oxazole 5 und 14, 2(5H)-Furanone 8 oder 6H-1,3-Oxazin-6-one 9. Aus N-Thiobenzoylasparaginsäure, Acetanhydrid und 3-Picolin entsteht das 6H-1,3-Thiazin-6-on (12). Glutaminsäure wird von Acetanhydrid und 4-(Dimethylamino)pyridin in guter Ausbeute in 1,5-Diacetyl-2-pyrrolidon (22) übergeführt. Mechanismen für die Bildung der verschiedenen Produkte werden diskutiert.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.197419741104
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