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Synlett 2022; 33(08): 795-799
DOI: 10.1055/a-1796-7444
DOI: 10.1055/a-1796-7444
letter
[4+2]-Cycloaddition Reactions of Aza-o-quinone Methides with Fulvenes: Construction of Tetrahydroquinoline Derivatives
We are grateful to the National Natural Science Foundation of China (No. 21702155), the Scientific Research Project of the Hubei Provincial Department of Education (No. B2019055), and the Open Project of the Key Laboratory of Green Chemical Engineering Processes of the Ministry of Education (No. GCP20190202) for financial support.
Abstract
An efficient [4+2] cycloaddition reaction of fulvenes with aza-o-quinone methides, generated in situ from N-(o-chloromethyl)aryl sulfonamides with the assistance of a base, has been developed to afford a series of tetrahydroquinoline derivatives. The reaction tolerates a wide range of aza-o-quinone methides and fulvenes bearing four- to seven-membered rings to afford the corresponding tetrahydroquinolines in moderate to good yields. Based on a literature analysis, a plausible mechanism for this [4+2] cycloaddition is proposed.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1796-7444.
- Supporting Information
Publication History
Received: 12 February 2022
Accepted after revision: 13 March 2022
Accepted Manuscript online:
13 March 2022
Article published online:
13 April 2022
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