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Oxone-DMSO Triggered Methylene Insertion and C(sp2)-C(sp3)-H-C(sp2) Bond Formation to Access Functional Bis-Heterocycles. 2020
Jaspreet Kour, and
Vunnam Venkateswarlu, and
Praveen K Verma, and
Yaseen Hussain, and
Gurudutt Dubey, and
Prasad V Bharatam, and
Subash C Sahoo, and
Sanghapal D Sawant
Medicinal Chemistry Division, CSIR-Indian Institute of Integrative Medicine, Canal Road, Jammu 180001, India.
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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