Department of Chemistry, Indian Institute of Technology Hyderabad (IITH) , Kandi, Sangareddy 502 285, Telangana, India.
J Org Chem. 2017 Jan 6;82(1):331-342. doi: 10.1021/acs.joc.6b02423. Epub 2016 Dec 12.
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.
发展了一种在有氧条件下通过镍催化配体/无碱的氧化异氰化物插入反应，以分子内双伯胺亲核试剂合成喹唑啉衍生物的有效方法。还证明了一种涉及异邻苯二甲酸酐开环和苯并咪唑环化以及进一步的镍催化分子内异氰化物插入的一锅法顺序双环化级联（SDAC）策略。该方法操作简单，可使用多种底物，并为多种 C-N 键形成提供了新方法。该方法已成功应用于通过脱保护-GBB 反应序列合成迄今为止未报道的咪唑并[2,1-b]苯并咪唑并喹唑啉。此外，荧光研究表明本策略具有发现高荧光探针的潜力。
