Oxone-DMSO Triggered Methylene Insertion and C(sp2)−C(sp3)-H−C(sp2) Bond Formation to Access Functional Bis-Heterocycles

Kour, Jaspreet ; Venkateswarlu, Vunnam ; Verma, Praveen K. ; Hussain, Yaseen ; Dubey, Gurudutt ; Bharatam, Prasad V. ; Sahoo, Subash C. ; Sawant, Sanghapal D. (2020) Oxone-DMSO Triggered Methylene Insertion and C(sp2)−C(sp3)-H−C(sp2) Bond Formation to Access Functional Bis-Heterocycles The Journal of Organic Chemistry, 85 (7). pp. 4951-4962. ISSN 0022-3263

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Official URL: http://doi.org/10.1021/acs.joc.9b03477

Related URL: http://dx.doi.org/10.1021/acs.joc.9b03477

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.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:116259
Deposited On:12 Apr 2021 09:15
Last Modified:12 Apr 2021 09:15

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