Dioxopyrrolines. LX. Cycloaddition Reaction of 4-Benzoyl-5-ethoxycarbonyl-1-phenyl-1H-pyrrole-2, 3-dione to Olefins : An Inverse-Electron-Demand Hetero Diels-Alder Reaction

Thermal cycloaddition of 4-benzoyl-5-ethoxycarbonyl-1-phenyl-1H-Pyrrole-2, 3-dione (dioxopyrroline) 1 to electron-rich olefins smoothly proceeded in a highly regio- and stereoselective manner to give pyranopyrrole derivatives in excellent yields. The reaction is a typical inverse-electron-demand het...

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Veröffentlicht in:	Chemical & pharmaceutical bulletin 1996/04/15, Vol.44(4), pp.670-674
Hauptverfasser:	HORIGUCHI, Yoshie, SANO, Takehiro, TSUDA, Yoshisuke
Format:	Artikel
Sprache:	eng
Schlagworte:	1H-pyrrole-2, 3-dione Chemistry dioxopyrroline Exact sciences and technology hetero Diels-Alder reaction Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms Organic chemistry Preparations and properties pyranopyrrole thermal cyloaddition reaction
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Beschreibung
Zusammenfassung:	Thermal cycloaddition of 4-benzoyl-5-ethoxycarbonyl-1-phenyl-1H-Pyrrole-2, 3-dione (dioxopyrroline) 1 to electron-rich olefins smoothly proceeded in a highly regio- and stereoselective manner to give pyranopyrrole derivatives in excellent yields. The reaction is a typical inverse-electron-demand hetero Diels-Alder reaction, in which dioxopyrroline behaves as an electron-deficient diene.
ISSN:	0009-2363 1347-5223
DOI:	10.1248/cpb.44.670