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C(sp2)–H Functionalization of 2H‑Indazoles at C3-Position via Palladium(II)-Catalyzed Isocyanide Insertion Strategy Leading to Diverse Heterocycles

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journal contribution
posted on 08.03.2016, 00:00 by Shinde Vidyacharan, Arumugavel Murugan, Duddu S. Sharada
Herein, we have reported an efficient Pd-catalyzed C–H functionalization of 2H-indazole at C3-position via an isocyanide insertion strategy for the synthesis of unprecedented benzoxazinoindazoles, indazoloquinaoxalines and benzoxazinoindazolones for the first time. Our new method provides an operationally simple and versatile route for a selective synthesis of 2-(2H-indazol-2-yl)­phenols. Furthermore, we developed a sequential one-pot strategy for the synthesis of benzoxazinoindazolone under metal-oxidant-free conditions. We also achieved the isocyanide insertion between C­(sp2)–H and oxygen heteroatom for the first time. The key features of the present protocol are construction of 4 bonds in one-pot, synthesis of new skeletally diverse scaffolds, broad substrate scope, high yields and environmentally benign conditions.