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General and Regioselective Synthesis of Substituted Pyrroles by Metal-Catalyzed or Spontaneous Cycloisomerization of ( Z )-(2-En-4-ynyl)amines

✍ Scribed by Gabriele, Bartolo; Salerno, Giuseppe; Fazio, Alessia


Book ID
126111292
Publisher
American Chemical Society
Year
2003
Tongue
English
Weight
154 KB
Volume
68
Category
Article
ISSN
0022-3263

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Z)-(2-En-4-ynyl)amines 1 bearing an internal triple bond undergo smooth cycloisomerization into pyrroles 2 in the presence of catalytic amounts of PdCl 2 in conjunction with KCl at 25-100Β°C in anhydrous N,N-dimethylacetamide. When the triple bond is terminal, spontaneous uncatalyzed cyclization to t

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## Abstract The oxidative carbonylation of readily available (__Z__)‐(2‐en‐4‐ynyl)amines, catalyzed by the PdI~2~‐KI system, selectively afforded in satisfactory yields (40–95 %) either pyrrole‐2‐acetic ester or (pyridine‐2‐one)‐3‐acetic amide derivatives, depending on the susbtitution pattern of t