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A First Resource‐Efficient and Highly Flexible Procedure for a Four‐Component Synthesis of Dispiropyrrolidines
Author(s) -
Li Ming,
Yang WenLong,
Wen LiRong,
Li FengQi
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800035
Subject(s) - isatin , chemistry , knoevenagel condensation , sarcosine , aldehyde , azomethine ylide , cycloaddition , tandem , 1,3 dipolar cycloaddition , combinatorial chemistry , catalysis , component (thermodynamics) , organocatalysis , organic chemistry , enantioselective synthesis , amino acid , glycine , biochemistry , materials science , physics , composite material , thermodynamics
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. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)