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A Novel Aza-Nazarov Cyclization of Quinazolinonyl Enones: A Facile Access to CRing Substituted Vasicinones and Luotonins
preprintsubmitted on 04.10.2019, 22:12 and posted on 09.10.2019, 20:03 by Sivappa Rasapalli, Vamshisammeta Reddy Sammeta, Zachary F Murphy, Yanchang Huang, Jeffrey A Boerth, James A Golen, Sergey N Savinov
Our pre-print titled " A Novel Aza-Nazarov Cyclization of Quinazolinonyl Enones: A Facile Access to C-Ring Substituted Vasicinones and Luotonins" describes:· design and development of a novel variant of aza-Nazarov reaction of quinazolinonyl enones as a methodology to access pyrroloquinazolinones (14 examples)· identification of reaction conditions to achieve two types of pyrroloquinazolinones i.e., linear vs angular, through the intrinsic divergence built in to the enones· detailed computational investigation of the mechanism of this novel cyclization· application in diastereoselctive synthesis of C-ring substituted vasicinones (14 analogues)· application in synthesis of C-ring substituted luotonins (14 analogues)