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. 2007 Jan 24;12(1):49-59.
doi: 10.3390/12010049.

Microwave-assisted synthesis of substituted hexahydro-pyrrolo[3,2-c]quinolines

Michal Neuschl  1 , Darek Bogdal, Milan Potacek
Affiliations

Microwave-assisted synthesis of substituted hexahydro-pyrrolo[3,2-c]quinolines

Michal Neuschl et al. Molecules. .

Abstract

New compounds with the ethyl hexahydro-1H-pyrrolo[3,2-c]quinoline-2-carboxylate skeleton were prepared by microwave-assisted intramolecular 1,3-dipolar cycloaddition reactions. The reactions were carried out under solvent-free conditions and compared with the same reaction in the presence of a solvent and a catalyst. Steric effects on the selectivity of the reaction were noted and evaluated.

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Figures

Scheme 1
Scheme 1
Scheme 2
Scheme 2
Scheme 3
Scheme 3
Scheme 4
Scheme 4
The proposed mechanism of the investigated reaction.
Figure 1
Figure 1
Conversion of aldehyde 4 in the presence of amine 5a to the diastereomeric mixture 6 under microwave irradiation at 215 °C.
Scheme 5
Scheme 5
Figure 2
Figure 2
Preferred geometry of the ylide.
Scheme 6
Scheme 6
Schematic depiction of the transition states TS A and TS B during the reaction and configuration at the products 6 and 6´.
Scheme 7
Scheme 7
Optimized view of the compounds 6a and 6´a.
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