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The meyer‐schuster rearrangement and hydrohalide addition of 3‐alkynyl‐3‐hydroxy‐1 H ‐isoindol‐1‐ones
Author(s) -
Omar Enouri A.,
Tu Chi,
Wigal Carl T.,
Braun Loren L.
Publication year - 1992
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.5570290445
Subject(s) - chemistry , tetrahydrofuran , halide , hydrolysis , yield (engineering) , lithium (medication) , aqueous solution , medicinal chemistry , organic chemistry , medicine , materials science , solvent , metallurgy , endocrinology
Abstract Treatment of N ‐methyl and N ‐phenylphthalimide with appropiate lithium acetylides in tetrahydrofuran obtained the acetylenic alcohols 2a through 2h . These compounds, when subjected to mildly acidic hydrolysis conditions in aqueous organic solvents, underwent Meyer‐Schuster rearrangement to yield the α,β‐unsaturated carbonyl compounds 4a through 4h which were determined to have the E configuration. The phenyl ethynyl analogs of series 4 underwent hydrohalide addition when treated with hydrogen halides in water solution.