35567-59-0Relevant articles and documents
Hammet constants effects in microwave cascade etherification-cyclization- krapcho reaction to access [2,3]-dihydrobenzofuran-3-ones from salicylic derivatives
Farran, Daniel,Bertrand, Philippe
, p. 989 - 1001 (2012/02/05)
Two methods were evaluated for the synthesis of substituted [2,3]-dihydro-2-methyl-benzofuran-3-ones from corresponding salicylate esters under microwave irradiation. A two-step sequence via ether intermediates was convenient for various substituted salic
Unexpected Migration and Oxidative Cyclization of Substituted 2-Acetophenone Triflates under Basic Conditions: Synthetic and Mechanistic Insights
Coe, Jotham W.,Bianco, Krista E.,Boscoe, Brian P.,Brooks, Paige R.,Cox, Eric D.,Vetelino, Michael G.
, p. 9964 - 9970 (2007/10/03)
Oxidative ring closure of alkyl-substituted 2-hydroxyacetophenone trifluoromethanesulfonate esters (triflates) occurs upon exposure to base in anaerobic DMF at 20-90 °C. Alkyl substitution is required for ring closure. A migrated enol triflate product forms at lower temperature in high yield via migration of the trifluoromethanesulfonate in the unsubstituted and monoalkyl-substituted cases. The alkyl-substituted enol triflates also enter into the benzofuran-3-one ring-forming process under thermal cyclization conditions. Potential mechanistic pathways are evaluated.