Three-component synthesis of novel spiro[4H-pyran-3,3΄-oxindoles] using 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1,2-dione

Spirooxindole systems are of great interest in a modern organic, medicinal, and natural product chemistry. This type of framework has been found as a core structure of many natural alkaloids with promising pharmacological activity, such as horsfiline, gelsemine, mitraphylline, spirotryprostatins A, B, and others. The pyrane/chromene-based heterocycles that fuse with an oxindole ring system represent a potentially promising subset of the tetrahydropyranone and pyrrolidinyl spirooxindole natural products.1-3 Therefore, in this work, we report the synthesis of some new spiro[4H-pyran-3,3΄-oxindoles] 4 by the three component reaction of keto-lactam 1, substituted cyanomethyl aryl ketones 2 and malononitrile or ethyl cyanoacetate 3 in the presence of 4-(N,N-dimethylamino)pyridine (DMAP) in refluxing EtOH (Figure 1).

کلیدواژه ها:

Three-component reactions ، Spirooxindoles ، Cyanomethyl aryl ketones ، Malononitrile ، Ethyl cyanoacetate.