Nickel-Catalyzed Aerobic Oxidative Isocyanide Insertion: Access to Benzimidazoquinazoline Derivatives via Sequential Double Annulation Cascade (SDAC) strategy

Shinde, A H and Arepally, S and Baravkar, M D and D S, Sharada (2017) Nickel-Catalyzed Aerobic Oxidative Isocyanide Insertion: Access to Benzimidazoquinazoline Derivatives via Sequential Double Annulation Cascade (SDAC) strategy. The Journal of Organic Chemistry, 2017 (82). pp. 331-342. ISSN 0022-3263

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Abstract

An efficient protocol for the synthesis of quinazoline derivatives through nickel-catalyzed ligand/base-free oxidative isocyanide insertion under aerobic conditions with intramolecular bis-amine nucleophiles has been developed. A one-pot sequential double annulation cascade (SDAC) strategy involving an opening of isatoic anhydride and annulation to benzimidazole and further nickel-catalyzed intramolecular isocyanide insertion has also been demonstrated. The method is operationally simple to implement with wide substrates and represents a new approach for multiple C-N bond formations. The methodology has been successfully applied for the syntheses of hitherto unreported imidazo fused benzimidazoquinazoline via deprotection-GBB reaction sequence. Further, the florescence study reveals the potential of the present strategy for discovery of highly fluorescent probes.

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