Method for the synthesis of ferrocene and pyridone derivatives directed by n-methoxy formamide

Abstract

The invention discloses an N-methoxyl formamide-orientated method for synthesizing a ferrocene and pyridone derivative. According to the method, under the conditions that palladium acetate is taken as a catalyst, copper acetate is taken as a catalyst promoter and quaternary ammonium salt and alkali are taken as additives, an N-methoxyl ferrocene and [c] pyridine-2(1H)-ketone derivative is obtained by carrying out a cyclization reaction on N-methoxyl ferrocene formamide and alkyne. The method adopts an N-methoxyl formamide-orientated carbon-hydrogen bond and nitrogen-hydrogen bond double-activation reaction to synthesize the N-methoxyl ferrocene and [c] pyridine-2(1H)-ketone derivative in one step. The organometallic condensed heterocyclic compounds are unique in structure, thus being hard to prepare by a conventional method; the method provided by the invention has the characteristics of being easy in obtaining of raw materials and mild in reaction conditions, not needing the protection of inert gas, being high in synthetic yield, and the like; therefore, a new way is provided for the synthesis of novel ferrocene and heterocyclic compounds, and the method has an important significance for expanding the application of the compounds in the fields such as medicinal chemistry, material chemistry, catalysts and the like.

Description

technical field [0001] The present invention relates to a ferrocenyl pyridone condensed heterocyclic compound and a synthesis method thereof, in particular to a N-methoxyferrocene[c]pyridin-2(1H)-one derivative and its synthesis method. Background technique [0002] Heterocyclic compounds are a class of cyclic organic compounds containing heteroatoms, most of which have important biological activities. Various heterocyclic structures are widely found in natural products and chemical molecular structures such as drugs, pesticides, herbicides, and dyes ( (a) Michael J.P. Nat. Prod. Rep., 2008, 25, 139. (b) Michael J. P. Nat. Prod. Rep., 2007, 24, 191. (c) Michael J. P. Nat. Prod. Rep., 2005, 22, 603.). Therefore, the research on heterocyclic compounds, especially the research on the synthesis methodology of fused heterocyclic compounds has always been favored. [0003] Ferrocene and its derivatives are a very important class of organometallic compounds, and their core skelet...

AI Technical Summary

Problems solved by technology

Wherein, in the patent (CN 103788137A) disclosed by Wang Baiquan etc., although described with N-alkylformamide and N-aryl (these aryls include ester group, methoxy group and various halogen substituted benzene ring substituents) Formamide-directed carbon-hydrogen bond and nitrogen-hydrogen bond activation reaction, synthesized a series of ferrocene and heterocyclic derivatives at 90-100 ° C, but the synthesized compounds are not easy to be further converted into other N-substituted Ferrocene and heterocyclic derivatives have certain limitations in application

And the synthesis of N-methoxyferroceno[c]pyridin-2(1H)-ones based on N-methoxyformamide (MeONHCO-) ​​has not been reported

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