Isocyanide-based multicomponent reactions: concise synthesis of spirocyclic oxindoles with molecular complexity by using a [1,5]-hydrogen shift as the key step.
A concise multicomponent reaction of isocyanide, α-substituted allenoate, and methyleneindolinone has been disclosed. This protocol provides a fast and straightforward approach to synthesize unusual tricyclic oxindoles in an efficient and atom-economic manner. Mechanistically, the present cycloaddition may proceed through a cascade sequence involving double Michael addition, double cyclization, double [1,5]-hydrogen shift, and group migration. The introduction of a special alkyl group to the allenoate is believed to play a key role in the cascade reaction. This method also features a broad substrate scope, which is particularly useful for the delivery of a large number of compounds.
Department of Chemistry, Innovative Drug Research Center, Shanghai University, 99 Shangda Road, Shanghai, 200444 (P. R. China), Fax: (+86) 21-66132408.
Shikuan
S
Su
Chunju
C
Li
Xueshun
X
Jia
Jian
J
Li
D020650:Combinatorial Chemistry Techniques; D003486:Cyanides / Q000138:chemical synthesis / Q000737:chemistry*; D003500:Cyclization; D006859:Hydrogen / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D009281:Naphthalenes / Q000138:chemical synthesis / Q000737:chemistry; D000078183:Oxindoles; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D003486:Cyanides; D007211:Indoles; D009281:Naphthalenes; D000078183:Oxindoles; D013141:Spiro Compounds; C022960:2-oxindole; D006859:Hydrogen; C110055:allenolic acid
allenoates; hydrogen shift; isocyanides; multicomponent reactions; spirocyclic oxindoles