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

✍ Scribed by Charles W. Jefford; William Johncock

Publisher
John Wiley and Sons
Year
1983
Tongue
German
Weight
337 KB
Volume
66
Category
Article
ISSN
0018-019X

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✦ Synopsis

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‐(3__H__)‐one (4a) and 5,6‐dihydroindolizin‐7 (8__H__)‐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 (8__H__)‐one (10) and 4‐(3‐methylindol‐1‐yl)‐but‐l‐en‐3‐one (11) in 7% and 24% yield, respectively.

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