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

Autor:	Mayur D. Baravkar, Anand H. Shinde, Sagar Arepally, Duddu S. Sharada
Rok vydání:	2016
Předmět:	Benzimidazole Annulation 010405 organic chemistry Stereochemistry Isocyanide Organic Chemistry chemistry.chemical_element 010402 general chemistry 01 natural sciences 0104 chemical sciences Catalysis chemistry.chemical_compound Nickel chemistry Nucleophile Cascade Intramolecular force
Zdroj:	The Journal of Organic Chemistry. 82:331-342
ISSN:	1520-6904 0022-3263
Popis:	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 a wide variety of substrates and represents a new approach for multiple C-N bond formations. The methodology has been successfully applied to the syntheses of hitherto unreported imidazo-fused benzimidazoquinazolines via a deprotection-GBB reaction sequence. Further, a florescence study reveals the potential of the present strategy for the discovery of highly fluorescent probes.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::e01b3b4c40c68967cbde4ca2af4431b5 https://doi.org/10.1021/acs.joc.6b02423 Zobrazit plný text záznamu