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An anomalous reaction of a 4-chlorocoumarin dimer with amines: the formation of benzopyranocoumarin derivatives from the dimer

✍ Scribed by Masaki Hasegawa; Hirohiko Miura; Masayuki Kuroda; Minoru Hayashi; Yukihiko Hashimoto; Kazuhiko Saigo

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
220 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

Reaction of an anti head-to-tail 4-chlorocoumarin dimer with amines afforded benzopyranocoumarin derivatives in high yields; the reaction is quite different from the expected reaction of coumarin dimer derivatives with amines. On the basis of spectral information, a possible reaction mechanism is proposed through a tandem lactone ringopening reaction, elimination, cycloreversion of cyclobutene, addition-elimination, and Michael addition.

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