Oxone-DMSO Triggered Methylene Insertion and C(sp<sup>2</sup>)−C(sp<sup>3</sup>)-H−C(sp<sup>2</sup>) Bond Formation to Access Functional Bis-Heterocycles
Jaspreet Kour, Vunnam Venkateswarlu, Praveen Kumar Verma, Yaseen Hussain, Gurudutt Dubey, Prasad V. Bharatam, Subash C. Sahoo, Sanghapal D. Sawant
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.
Topics & Concepts
MethyleneChemistryPyrazoleMoleculeInsertion reactionCenter (category theory)Medicinal chemistryTandemStereochemistryDensity functional theoryComputational chemistryCrystallographyOrganic chemistryCatalysisComposite materialMaterials scienceCatalytic C–H Functionalization MethodsCyclopropane Reaction MechanismsSynthesis and Catalytic Reactions