4.7 Article

Tandem Michael-anti-Michael Addition-Mediated Orthogonal Strapping of Diynones: Regioselective Spirocyclopentannulation of Oxindoles and Pyrazolones and DFT Validation

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JOURNAL OF ORGANIC CHEMISTRY
卷 87, 期 1, 页码 884-891

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AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c02667

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  1. Council of Scientific and Industrial Research (CSIR)
  2. Department of Science and Technology (DST), New Delhi [GAP-584]
  3. Science and Engineering Research Board [PDF/2020/001111]
  4. Dr. Reddy's Laboratory (DRL)

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An efficient protocol for the synthesis of orthogonally strap diynones through one pot transition-metal-free reaction has been developed. Insights into the regioselective tandem Michael-anti-Michael processes have been gleaned through DFT calculations.
An efficient protocol involving the transformation of sequentially generated recursive anions from heterocyclic precursors to orthogonally strap diynones through one pot transition-metal-free spirocyclopentannulation has been devised, employing oxindoles and pyrazolones as prototypical platforms. Insights into these regioselective tandem Michael-anti-Michael processes have been gleaned through DFT calculations.

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