AI Article Synopsis
- The aza-Prins reaction of a specific tetrahydroquinoline compound with 1,2-dicarbonyl compounds was successful, yielding tricyclic benzazocines in 20-86% yields under HCl conditions.
- The reaction demonstrated stereoselectivity, particularly favoring the formation of the 2,4- isomer, and when combined with an enantiopure ketoester, produced a mixture of diastereomers.
- These diastereomers were separable, allowing for the creation of enantiopure tricyclic benzazocines and also facilitating the synthesis of spirooxindole derivatives using isatin derivatives.
Article Abstract
The aza-Prins reaction of 6,7-dimethoxy-3-vinyl-1,2,3,4-tetrahydroquinoline () with 1,2-dicarbonyl compounds proceeded smoothly in the presence of HCl, and the corresponding tricyclic benzazocines were isolated in yields of 20-86%. The reaction proceeded in a stereoselective manner, and the formation of the 2,4- isomer was observed. The reaction of with an enantiopure ketoester gave the corresponding tricyclic benzazocine as a mixture of diastereomers. The diastereomers were easily separated and converted to enantiopure tricyclic benzazocines. The synthesis of spirooxindole derivatives was achieved by the reaction of with isatin derivatives.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8650011 | PMC |
| http://dx.doi.org/10.1021/acs.joc.1c01785 | DOI Listing |
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