Free accessResearch articleFirst published online 2000-10
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 †
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.
NoguchiM., AkaoR., GotohM., KawamotoH., KakehiA., J. Chem. Res. Submitted to
3.
InazumiT., YamadaK., KurokiY., KakehiA., NoguchiM., J. Chem. Soc., Perkin Trans. 1, 1994, 557; M. Gotoh, T. Mizui, B. Sun, K. Hirayama, M. Noguchi, J. Chem. Soc., Perkin Trans. 1, 1995, 1857.
4.
NoguchiM., MizukoshiT., KakehiA., Tetrahedron, 1996, 52, 13081; M. Noguchi, T. Mizukoshi, T. Uchida, Y. Kuroki, Tetrahedron, 1996, 52, 13097; M. Noguchi, T. Mizukoshi, S. Nakagawa, A. Kakehi, Tetrahedron, 1996, 52, 13111.