Use of 3-halo-1-azaallylic anions in heterocyclic
N. Giubellina, W. Aelterman, and N. De Kimpe
Department of Organic Chemistry, Faculty of Agricultural and
Applied Biological Sciences, Ghent University, Coupure links 653, B-9000
Abstract: The synthetic potential of lithio 3-halo-1-azaallylic
anions as building blocks in organic chemistry and especially in heterocyclic
chemistry will be highlighted by the synthesis of functionalized imines,
obtained after reaction of 3-halo-1-azaallylic anions with het- eroatom-substituted
electrophiles. Thus, the latter generated functionalized imines are
suitable building blocks for the synthesis of a whole range of heterocycles
and physiologically active compounds, including agrochemicals and pharmaceuticals.
3-Halo-1-azaallylic anions were used in the synthesis of N-alkyl-3,3-dichloroazetidines,
2,3-disubstituted pyrroles, piperidines, 2-substituted pyridines, 2-alkoxytetrahydrofurans,etc.,
from which a large range of useful and interesting chemicals can be
produced, e.g., 2-azetines and 9-alkyl- 2-phenyl-3a-beta,4,6,7,8,9,9a-beta,9b-beta-octahydro-1H-pyrrolo
[3,4,h]quinoline-1,3-diones. The utility of the present methodology
is demonstrated by the synthesis of the pheromone (S)-manicone, the
sulfur-containing flavor compound 2-[(methylthio)methyl ]-2-butenal,
and some agrochemical and pharmaceutical compounds.
*Lecture presented at the 4th Florida Heterocyclic
Conference, Gainesville, Florida, 10-12 March 2003. Other presentations
are published in this issue, pp. 1403-1475.
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