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Differences in reactions of vinyl derivatives of pyrrole and thiophene with acetylenic esters
Author(s) -
Lee Chang Kiu,
Ahn Yu Mi
Publication year - 1989
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.5570260224
Subject(s) - chemistry , thiophene , regioselectivity , adduct , pyrrole , cycloaddition , reactivity (psychology) , propenyl , medicinal chemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology
1‐Methyl‐2‐vinylpyrrole and 2‐vinylthiophene showed remarkable differences in reactivity and regioselectivity upon reaction with methyl propiolate, respectively forming dimethyl 1‐methylindole‐4,7‐dicarboxylate and dimethyl benzo[ b ]thiophene‐4,6‐dicarboxylate. 1‐Methyl‐2‐(1‐propenyl)pyrrole reacted with dimethyl ace‐tylenedicarboxylate to give Diels‐Alder and Michael‐type adducts. On the other hand, 2‐(1‐propenyl)thiophene gave a 1:2 adduct which results via an initial cycloaddition and subsequent ene reaction.