Rh-Catalyzed Ring-opening Rearrangement Of N-Sulfonyl Triazoles For The Synthesis Of 6-Alkoxy Piperidin-3-ones

6-Alkoxypiperidin-3-one structures are widely found in natural products and drug molecules,which have important biological and pharmacological activities,and their synthesis has always received more attention.The aza-Achmatowicz reaction is an important route for the synthesis of 6-alkoxy piperidin-3-ones,which is requested a three-step procedure.At the same time,the construction of 6-alkoxy piperidin-3-ones bearing quaternary carbons at C4 or C5 position has not yet been explored.Therefore,searching for some supplementary methodologies to obtain structural diversity of 6-alkoxy piperidin-3-ones in a step-economical and practical version are highly desirable.At present,N-sulfonyl-1,2,3-triazoles have been widely reported as α-imine metal carbine precursors to participate in various types of reactions,thereby constructing various nitrogen-containing heterocyclic compounds.In this thesis,Rh-catalyzed ring-opening rearrangement of N-sulfonyl triazoles for the synthesis of 6-alkoxy piperidin-3-ones is reported.It mainly includes the following two parts:The first part: introduction of the application of 6-alkoxy piperidin-3-ones in the synthesis and synthesis of such compounds;Preparation of N-sulfonyltriazole and its participating reactions are briefly introduced.The second part: gives a brief introduction to the research background,and then describes the experimental process and the experimental results.In summary,a step-economical and practical synthesis of 6-alkoxy piperidin-3-ones based on a novel rhodium(II)-catalyzed tandem cyclization of aliphatic N-sulfonyl triazoles and various alcohols has been developed for the first time.The condition of reaction is mild,the operation is simple,and various alcohols and N-sulfonyl triazole compounds can be well tolerated.The reaction simultaneously realized the synthesis of 6-alkoxy piperidin-3-ones with C4 and C5 positions as quaternary carbon centers and provided a powerful supplementary method for the traditional aza-Achmatowicz reaction.