Preparation of 9,9-Disubstituted 4,5-Diazafluorenes Useful as Cognitive Enhancers

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• 作者：Timothy D. Costello ; James H. Jensen ; Christopher A. Teleha ; and Matthew E. Voss
• 刊名：Organic Process Research & Development
• 出版年：1997
• 出版时间：November 1997
• 年：1997
• 卷：1
• 期：6
• 页码：407 - 410
• 全文大小：93K
• 年卷期：v.1,no.6(November 1997)
• ISSN：1520-586X

文摘

A novel synthesis of symmetric and nonsymmetric 9,9-disubstituted 4,5-diazafluorenes has been developed. Thesecompounds have activity in both an in vitro acetylcholinereleaseassay and in vivo rodent models of learning andmemory.Preparation of these compounds involves a uniquealdolcondensation between 4,5-diazafluoren-9-one (4) and4-picoline.Reduction of aldol product 5(5-(4-pyridinylmethylene)-5H-cyclopenta[2,1-b:3,4-b']dipyridine)provides monoalkylated diazafluorene 6(5-(4-pyridinylmethyl)-5H-cyclopenta[2,1-b:3,4-b']dipyridine) which proved to be a key intermediateforsynthesis of nonsymmetric analogs.