Helvetica chimica acta

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

CW Jefford, W Johncock

Index: Jefford, Charles W.; Johncock, William Helvetica Chimica Acta, 1983 , vol. 66, # 8 p. 2666 - 2671

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Citation Number: 20

Abstract

Abstract 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- ...