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Heterocycles through Domino Reactions with Trimethyl Aconitate, a Versatile Synthetic Building Block
Author(s) -
Witthaut Daniel,
Fröhlich Roland,
Schäfer Hans J.
Publication year - 2001
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20011119)40:22<4212::aid-anie4212>3.0.co;2-n
Subject(s) - domino , block (permutation group theory) , domino effect , chemistry , combinatorial chemistry , organic chemistry , mathematics , physics , catalysis , geometry , nuclear physics
The multitalented synthetic reagent trimethyl aconitate ( 1 ) is a renewable raw material with a high density of functional groups that up to now has only been scarcely used as a C 6 building block. Domino reactions with 1 consisting of imine additions and intramolecular acylations provide simple access to heteropolycycles in one‐pot reactions. For example, 1 reacts with N ‐methylbenzylidenamine ( 2 ) to give the spiro[pyrrolidinone‐3,3′‐dihydropyrrolinone] 3 in 40 % yield (see scheme).