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

Alizadeh Babak H. | Zendy; Foroumadi Alireza | Zendy; Shafiee Abass | Zendy

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

Author(s) -

Alizadeh Babak H.,

Foroumadi Alireza,

Shafiee Abass

Publication year - 2008

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.5570450340

Subject(s) - chemistry , resorcinol , reagent , ring (chemistry) , condensation , closure (psychology) , grignard reagent , organic chemistry , medicinal chemistry , physics , economics , market economy , thermodynamics

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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