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The acid‐catalyzed rearrangement of 1‐ N ‐allylindolines
Author(s) -
Izumi Taeko,
Kasahara Akira
Publication year - 1990
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570270502
Subject(s) - indoline , chemistry , catalysis , zinc , chloride , medicinal chemistry , quinoline , organic chemistry
Zinc chloride‐catalyzed rearrangement of 1‐ N ‐allylindoline and 1‐ N ‐(2‐methylallyl)indoline proceeds readily in refluxing xylene to give 7‐allylindoline and 7‐(2‐methylallyl)indoline in 73% and 86% yields, respectively. The reaction of 1‐ N ‐2‐butenylindoline and zinc chloride give rise to the mixture of 7‐(1‐methylallyl)indoline, 7‐( cis ‐ and trans ‐1‐methyl‐1‐propenyl)indoline, and 7‐( trans ‐2‐butenyl)indoline. On the other hand, the similar reaction of 1‐ N ‐(3‐methyl‐2‐butenyl)indoline with zinc chloride led to the formation of a mixture of 1,2,5,6‐tetrahydro‐4,4‐dimethyl‐4 H ‐pyrrolo[3,2,1‐ ij ]quinoline and 7‐(3‐methyl‐2‐butenyl)indoline.