Intramolecular Carbenoid Reactions of Pyrrole Derivatives Efficient Syntheses of Pyrrolizinone and Dihydroindolizinone

The copper-catalyzed pyrolysis of 1-diazo-3-(pyrrol-1-yl)-2-propanone (1a) and 1-diazo-4-(pyrrol-1-yl)-2-butanone (1b) in benzene solution gave 1 H-pyrrolizin-2-(3H)-one (4a) and 5,6-dihydroindolizin-7 (8H)-one (4b) , respectively, in quantitative yield. Similar pyrolysis of 1-diazo-4-(3-methylindol-1-yl)-2-butanone (9) was less efficient giving 1-methylbenzo[b]-5,6-dihydroindroindolizin-7 (8H)-one (10) and 4-(3-methylindol-1-yl)-but-l-en-3-one (11) in 7% and 24% yield, respectively.