Abstract
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.
Original language | English (US) |
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Pages (from-to) | 2934-2946 |
Number of pages | 13 |
Journal | ACS Omega |
Volume | 3 |
Issue number | 3 |
DOIs | |
State | Published - Mar 31 2018 |
Externally published | Yes |
Bibliographical note
Funding Information:The authors acknowledge UPE-2 and CSIR No. 02/200/ EMRII for the financial support. R.D. and R.P. acknowledge Central University of Rajasthan and CSIR for the fellowships, respectively.
Publisher Copyright:
© 2018 American Chemical Society.