The regioselective synthesis of spirooxindolo pyrrolidines and pyrrolizidines via three-component reactions of acrylamides and aroylacrylic acids with isatins and alpha-amino acids

作者：Pavlovskaya Tatyana L; Yaremenko Fedor G; Lipson Victoria V^*; Shishkina Svetlana V; Shishkin Oleg V; Musatov Vladimir I; Karpenko Alexander S

来源：Beilstein Journal of Organic Chemistry, 2014, 10: 117-126.

DOI：10.3762/bjoc.10.8

• acrylamides
• aroylacrylic acids
• azomethine ylide
• cyclative rearrangement
• cycloaddition
• multicomponent
• spirooxindoles

The regioselective three-component condensation of azomethine ylides derived from isatins and a-amino acids with acrylamides or aroylacrylic acids as dipolarophiles has been realized through a one-pot 1,3-dipolar cycloaddition protocol. Decarboxylation of 2'-aroyl-2-oxo-1,1', 2,2', 5', 6', 7', 7a'-octahydrospiro[indole-3,3'-pyrrolizine]-1'-carboxylic acids is accompanied by cyclative rearrangement with formation of dihydropyrrolizinyl indolones.

• 出版日期2014-1-9