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Rapid Synthesis of 3,7a-Diazacyclohepta[jk]fluorenes via Cascade Michael Addition/Pictet-Spengler Reaction and
Bei Wei1, Yanlong Gong1, Meng Xue1
1Medicinal Basic Research Innovation Center of Chronic Kidney Disease, Ministry of Education; School of Pharmacy, Shanxi Medical University, Taiyuan 030001, China.
Abstract:
In this article, a convenient method has been developed for the rapid and expedient diastereoselective synthesis of highly functionalized 3,7a-diazacyclohepta[jk]fluorenes from simple starting materials via a cascade Michael addition/Pictet-Spengler reaction and amidation reaction. In addition, the whole process, losing only one molecule of water and alcohol, has a high atomic economy.
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The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
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