Competitive azomethine ylide cycloaddition and carbonyl-ene reaction in the treatment of 4-(alk-2-enyl)amino-2-formylpyr-2(2H)-ones with sarcosine ethyl ester

Authors: Noguchi, Michihko; Akao, Ryosuke; Kawamoto, Hideyasu; Kuroki, Yoshiaki

Source: Journal of Chemical Research, Volume 2000, Number 10, October 2000 , pp. 470-471(2)

Publisher: Science Reviews 2000 Ltd

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Abstract:

The thermal reaction of 4-(alk-2-enyl)amino-2-formyl-2)2H)-pyrones 4 with sarcosine ethyl ester (2) gave two isomeric pyrrol[3,4-c]pyrano[4,3-d]pyridines 5 and 6, arising from the endo-cycloaddition of the resulting S- and W- shaped azomethine ylides, and [1,3]oxazines 8 via the carbonyl-ene reaction of pyrones 4 depending on the reaction conditions.

Document Type: Research article

DOI: 10.3184/030823400103165941

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