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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Oxone-DMSO Triggered Methylene Insertion and C(sp2)-C(sp3)-H-C(sp2) Bond Formation to Access Functional
Jaspreet Kour1,2, Vunnam Venkateswarlu1,2, Praveen K Verma1
1Medicinal Chemistry Division, CSIR-Indian Institute of Integrative Medicine, Canal Road, Jammu 180001, India.
Abstract:
Metal-free insertion of a methylene group was achieved for the construction of a new C(sp2)-C(sp3)-H-C(sp2) bond in order to prepare novel bis-heterocyclic scaffolds. The complete mechanistic investigations included experimental study and DFT calculations, and various symmetric and unsymmetric bis-pyrazoles as well as other pyrazole-based bis-heterocyclic molecules were prepared in moderate to high yields. Further modification of the bridged methylene group in the unsymmetric pyrazoles generated a chiral center to extend the scope of this method.
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