Journal
ORGANIC CHEMISTRY FRONTIERS
Volume 9, Issue 1, Pages 88-94Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1qo01414e
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Funding
- National Natural Science Foundation of China [22171029, 21901024, 21871252, 21801024, 21801026]
- Sichuan Science and Technology Program [2021YFS0315]
- Talent Program of Chengdu University [2081919035, 2081921038]
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A practical method for the synthesis of multisubstituted 2,3-dihydro-4H-quinolizin-4-ones has been developed using DBU as the catalyst. This transition metal free process features mild reaction conditions, wide functional group tolerance, easy scale-up synthesis, and versatile further derivatization, with satisfactory yields and excellent diastereoselectivities.
The reaction of 2-pyridylacetates and alpha,beta-unsaturated pyrazolamides with DBU as the catalyst has been developed. A range of unexplored multisubstituted 2,3-dihydro-4H-quinolizin-4-ones are obtained with satisfactory yields (up to 94%) and excellent diastereoselectivities (all cases >20 : 1 dr) via a dearomative [3 + 3] annulation process. This practical method also features transition metal free, mild reaction conditions, wide functional group tolerance, easy scale-up synthesis, and versatile further derivatization.
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