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Synthesis 2021; 53(07): 1349-1355
DOI: 10.1055/s-0040-1706549
DOI: 10.1055/s-0040-1706549
paper
DBU-Promoted Formal [4+2] Annulation Reactions of o-Chloromethyl Anilines with Azlactones
We gratefully acknowledge the Natural Science Foundation of Zhejiang Province (Grant No. LY20B020002) and the Fundamental Research Funds of Zhejiang Sci-Tech University (Grant No. 2020Q045) for financial support.
Abstract
An efficient 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)-mediated formal [4+2] annulation reaction of aza-ortho-quinone methides (aza-oQMs) (generated from o-chloromethyl anilines) with enolates (formed from azlactones) is disclosed, delivering biologically significant 3,4-dihydroquinolin-2(1H)-one derivatives in moderate to good yields. The salient features of this reaction include readily accessible starting materials, broad substrate scope, mild reaction conditions, removable protecting groups, and a scalable synthetic approach.
Key words
DBU - [4+2] annulation - aza-ortho-quinone methides - enolates - 3,4-dihydroquinolin-2(1H)-onesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1706549.
- Supporting Information
Publication History
Received: 11 August 2020
Accepted after revision: 23 September 2020
Article published online:
02 November 2020
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