Synthesis of conformationally restricted nicotine analogues by intramolecular [3+2] cycloaddition |
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| Authors: | Xiaobao Yang Shengjun Luo Fang Fang Yong Lu Hongbin Zhai |
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| Institution: | a Laboratory of Modern Synthetic Organic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
b Shanghai Key Laboratory of Green Chemistry and Chemical Processes (GCCP), Department of Chemistry, East China Normal University, Shanghai 200062, China |
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| Abstract: | We describe the synthesis of a series of conformationally constrained nicotine analogues 2-5 from appropriate pyridine-containing enals, featuring an intramolecular azomethine ylide-alkene 3+2] cycloaddition. The objective of the current project is to develop new selective nAChRs-targeting ligands. Of the nicotine analogues that we have studied, the conformation-restricting ring B unit can be either a five-membered carbocycle, or a six-membered carbocycle or heterocycle. The present work constitutes a general method for rapid assembly of other related tricyclic nicotine analogues. |
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| Keywords: | Conformationally restricted Intramolecular [3+2] cycloaddition Nicotine analogues Synthesis |
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