title: Multicomponent reaction to construct spirocyclic oxindoles with a Michael (triple Michael)/cyclization cascade sequence as the key step.
abstract: Multicomponent cycloadditions with readily available isocyanides, allenoates, and isatylidene malononitriles are disclosed. This reaction, which does not require the aid of any catalyst, allows the efficient syntheses of spirocyclic oxindoles with excellent regioselectivity. Reactions with ethyl 2,3-butadienoate and various structurally diverse α- and γ-substituted allenoates are also fully explored. Remarkably, we have shown that the usual three-component process can be further developed into an unprecedented four-component cycloaddition in the presence of water, which provides a new strategy to access highly unusual tricyclic oxindoles. From a synthetic point of view, this protocol is very interesting considering the high level of complexity reached in one step. The mechanism is thought to proceed by a triple Michael/cyclization process by using allenoate as a three carbon atom component (3 C). Furthermore, multicomponent reaction with γ-substituted allenoate also results in a very interesting conversion. In such cases, the unusual cleavage of the "C=C" double bond of isatylidene malononitrile and one of the "C=C" double bonds of allenoate is always observed.
authors: Department of Chemistry, Shanghai University, 99 Shangda Road, Shanghai, 200444, P.R. China. lijian@shu.edu.cn
authors: Jian
authors: J
authors: Li
authors: Ning
authors: N
authors: Wang
authors: Chunju
authors: C
authors: Li
authors: Xueshun
authors: X
authors: Jia
mesh_terms: D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D000078183:Oxindoles; D010879:Piperazines / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D007211:Indoles; D000078183:Oxindoles; D010879:Piperazines; D013141:Spiro Compounds; C478300:spirotryprostatin A; C022960:2-oxindole