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

Srinivasarao Yaragorla; Ravikrishna Dada; P. Rajesh; Manju Sharma

doi:10.1021/acsomega.8b00147

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

Srinivasarao Yaragorla, Ravikrishna Dada, P. Rajesh, Manju Sharma

Research output: Contribution to journal › Article › peer-review

15 Scopus citations

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)
Pages (from-to)	2934-2946
Number of pages	13
Journal	ACS Omega
Volume	3
Issue number	3
DOIs	https://doi.org/10.1021/acsomega.8b00147
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.

Publisher link

10.1021/acsomega.8b00147

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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. / Yaragorla, Srinivasarao; Dada, Ravikrishna; Rajesh, P. et al.
In: ACS Omega, Vol. 3, No. 3, 31.03.2018, p. 2934-2946.

Research output: Contribution to journal › Article › peer-review

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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.",

author = "Srinivasarao Yaragorla and Ravikrishna Dada and P. Rajesh and Manju Sharma",

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: {\textcopyright} 2018 American Chemical Society.",

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AU - Yaragorla, Srinivasarao

AU - Dada, Ravikrishna

AU - Rajesh, P.

AU - Sharma, Manju

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