TY - JOUR
T1 - Regioselective annulation of propargyl alcohols with ambident-enols
T2 - A Ca(II)-catalyzed trisubstituted benzochromene synthesis
AU - Yaragorla, Srinivasarao
AU - Pareek, Abhishek
AU - Dada, Ravikrishna
N1 - Publisher Copyright:
© 2017 Elsevier Ltd
PY - 2017/12/6
Y1 - 2017/12/6
N2 - 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.
AB - 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.
KW - Ambident nucleophiles
KW - Benzochromenes
KW - Calcium catalysis
KW - Claisen rearrangement
KW - Propargyl alcohols
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U2 - 10.1016/j.tetlet.2017.10.077
DO - 10.1016/j.tetlet.2017.10.077
M3 - Article
AN - SCOPUS:85033363078
SN - 0040-4039
VL - 58
SP - 4642
EP - 4647
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 49
ER -