Ibrahim Hamada Mohamed, Behbehani Haider
Chemistry Department, Faculty of Science, Kuwait University, P.O. Box 5969, Safat 13060, Kuwait.
Chemistry Department, Faculty of Science, Fayoum University, P.O. Box 63514, Fayoum 63514, Egypt.
J Org Chem. 2020 Dec 4;85(23):15368-15381. doi: 10.1021/acs.joc.0c02186. Epub 2020 Nov 4.
An appropriate and efficient Q-tube-assisted palladium-catalyzed strategy for the synthesis of novel, unparalleled diaza-dibenzo[,]azulene and diaza-benzo[]fluorene derivatives has been sophisticated, which includes oxygen and AcOH-induced oxidative C(sp)-C(sp) cross-dehydrogenative coupling reactions of 1-amino-2-imino-4-arylpyridine-3-carbonitriles with benzocyclic ketones such as benzosuberone, tetralone, thiochromone, and chromone, respectively. This Q-tube gas purging kit assisted-protocol features safe due to easy pressing and sealing, a wide substrate scope, easy workup and purifying phases, and the use of O as a benign oxidant, in addition to being scalable and having a high atom economy. The suggested mechanistic pathway includes a formal dehydrative step followed by palladium AcOH-induced C(sp)-C(sp) oxidative cross-coupling. In this study, X-ray crystallographic analysis has been used to authenticate the targeted products.
一种合适且高效的Q管辅助钯催化策略已被开发出来,用于合成新型、独特的二氮杂二苯并[,]薁和二氮杂苯并[]芴衍生物,该策略包括分别使1-氨基-2-亚氨基-4-芳基吡啶-3-腈与苯并环酮(如苯并环庚酮、萘满酮、硫代色酮和色酮)发生氧气和乙酸诱导的氧化C(sp)-C(sp)交叉脱氢偶联反应。这种Q管气体吹扫套件辅助方案具有安全性,因为其易于按压和密封,底物范围广,后处理和纯化阶段简便,并且使用氧气作为良性氧化剂,此外还具有可扩展性和高原子经济性。所提出的机理途径包括一个形式上的脱水步骤,随后是钯催化的乙酸诱导的C(sp)-C(sp)氧化交叉偶联。在本研究中,已使用X射线晶体学分析来验证目标产物。