Regioselective annulation of propargyl alcohols with ambident-enols: A Ca(II)-catalyzed trisubstituted benzochromene synthesis |
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| Authors: | Srinivasarao Yaragorla Abhishek Pareek Ravikrishna Dada |
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| Affiliation: | School of Chemistry, University of Hyderabad, P.O. Central University, Hyderabad 500046, Telangana, India |
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| Abstract: | Highly regioselective, 6-endo cyclization between propargyl alcohols and ambident enols such as naphthols, 4-hydroxy coumarin, cyclohexane-1,3-dione, 5,5-dimethylcyclohexane-1,3-dione is described using Ca(OTf)2 under solvent free conditions. The reaction proceeds through a cascade annulation which involves an etherification, Claisen type rearrangement, allene formation and endocyclization. Further, we extended this method to the synthesis of iodo-derivative and demonstrated the reactivity in cross-coupling reactions. |
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| Keywords: | Propargyl alcohols Ambident nucleophiles Benzochromenes Calcium catalysis Claisen rearrangement |
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