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New synthetic route towards 2,2-dimethylchromene and synthesis of substituted 7-(dimethylpropargyl)chromene

✍ Scribed by Babak H. Alizadeh; Alireza Foroumadi; Abass Shafiee

Book ID: 102341249
Publisher: Journal of Heterocyclic Chemistry
Year: 2008
Tongue: English
Weight: 336 KB
Volume: 45
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570450340

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✦ Synopsis

Abstract

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Trifluoromethansufonic acid (TFA) was found a proper reagent for regioselectively ring closure of resorcinol to afford 7‐hydroxy‐2,2‐dimethyl‐2,3‐dihydrochromen‐4‐one 3. The propargylation of 3 gave rise to 2,2‐dimethyl‐7‐(2‐methylbut‐3‐yn‐2‐yloxy)‐2,3‐dihydrochromen‐4‐one 4. Condensation of 4 with substituted phenyl or benzyl Grignard reagents afforded substituted phenyl or benzylidene chromenes 6a‐d and 4‐(substitutedbenzylidene)‐3,4‐dihydro chromenes 8a‐e, respectively.

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