4.5 Article

A first resource-efficient and highly flexible procedure for a four-component synthesis of dispiropyrrolidines

期刊

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2008, 期 16, 页码 2751-2758

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200800035

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azo compounds; ylides; multicomponent reactions; Knoevenagel condensation; cycloaddition; spiro compounds

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Two series of dispiropyrrolidine derivatives were successfully synthesized by a tandem Knoevenagel-1,3-dipolar cycloaddition reaction sequence of isatin or acenaphthylene-1,2-dione, sarcosine, 1,3-indanedione, and an aldehyde without any catalyst. This strategy is not only suitable to aromatic aldehydes but aliphatic and heteroaromatic aldehydes as well, Moreover, this one-pot, four-component synthesis of dispiropyrrolidines is the first of its kind, as the dipole azomethine ylide and dipolarophile can be generated in situ. Such a strategy would provide access to a fast one-pot synthesis of dispiroheterocycles, which are otherwise accessible only through multistep synthesis. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).

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