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Diazabutadienes in heterocyclic syntheses: reaction of 1,3-diazabutadienes with 2-oxazolin-5-ones

✍ Scribed by Bir Sain; Satyendra P. Singh; Jagir S. Sandhu

Book ID
104225841
Publisher
Elsevier Science
Year
1991
Tongue
French
Weight
101 KB
Volume
32
Category
Article
ISSN
0040-4039

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✦ Synopsis

4+2) Cycloaddition reactions of 1-aryl-4-dimethylamino-2-phenyl-1,3-diazabutadienes with 2-oxazolin-5-ones leading to pyrimidin-6-ones are reported.

Cycloaddition reactions of azadienes have received considerable attention in heterocyclic synthesis I. In this context 1~2-and 1,4-diazabutadienes have been extensively studied, in comparison 1,3-diazabutadiones have not received much attention2. Also, there are conflicting reports in the case of the reaction of ketanes Lrith 1,3-diazabutadienes2a.

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Reaction of 4-Substituted Aminomethylene-2-phenyl-2-oxazolin-5-ones with Primary Amines. -Reaction of the title 4aminomethyleneoxazolinones (I) with primary alkyl amines in MeCN provides regioselectively the transamination products (III) in excellent yields. Similar aminolysis with primary aryl ami