TY - JOUR
T1 - Highly Regioselective Synthesis of Oxindolyl-Pyrroles and Quinolines via a One-Pot, Sequential Meyer-Schuster Rearrangement, Anti-Michael Addition/C(sp3)-H Functionalization, and Azacyclization
AU - Yaragorla, Srinivasarao
AU - Dada, Ravikrishna
AU - Rajesh, P.
AU - Sharma, Manju
N1 - Publisher Copyright:
© 2018 American Chemical Society.
PY - 2018/3/31
Y1 - 2018/3/31
N2 - A one-pot, sequential Meyer-Schuster (MS) rearrangement of oxindole-derived propargyl alcohols to the corresponding α,β-unsaturated enones and their anti-Michael addition, followed by intramolecular azacyclization is described in a highly regioselective manner using Ca(OTf)2 as the promoter. Further, we described the one-pot MS rearrangement, followed by C(sp3)-H functionalization of 2-methyl azaarenes at α-carbon of these doubly activated alkenes. Control experiments and computational calculations were performed to propose the reaction mechanism.
AB - A one-pot, sequential Meyer-Schuster (MS) rearrangement of oxindole-derived propargyl alcohols to the corresponding α,β-unsaturated enones and their anti-Michael addition, followed by intramolecular azacyclization is described in a highly regioselective manner using Ca(OTf)2 as the promoter. Further, we described the one-pot MS rearrangement, followed by C(sp3)-H functionalization of 2-methyl azaarenes at α-carbon of these doubly activated alkenes. Control experiments and computational calculations were performed to propose the reaction mechanism.
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U2 - 10.1021/acsomega.8b00147
DO - 10.1021/acsomega.8b00147
M3 - Article
AN - SCOPUS:85043527172
SN - 2470-1343
VL - 3
SP - 2934
EP - 2946
JO - ACS Omega
JF - ACS Omega
IS - 3
ER -