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Synthesis 2021; 53(07): 1349-1355
DOI: 10.1055/s-0040-1706549
paper

DBU-Promoted Formal [4+2] Annulation Reactions of o-Chloromethyl Anilines with Azlactones

Haojie Ji
a   Department of Chemistry, Zhejiang Sci-Tech University, Hangzhou 310018, P. R. of China   eMail: jfxu@zstu.edu.cn
,
Chonglong He
a   Department of Chemistry, Zhejiang Sci-Tech University, Hangzhou 310018, P. R. of China   eMail: jfxu@zstu.edu.cn
,
Hongjie Gao
b   Pharmaron (Ningbo) Technology Development Co., Ltd., No. 800 Bin-Hai 4th Road, Hangzhou Bay New Zone, Ningbo 315336, P. R. of China
,
Weijun Fu
c   College of Chemistry and Chemical Engineering, and Henan Key Laboratory of Function-Oriented Porous Materials, Luoyang Normal University, Luoyang, Henan 471934, P. R. of China
,
Jianfeng Xu  ∗
a   Department of Chemistry, Zhejiang Sci-Tech University, Hangzhou 310018, P. R. of China   eMail: jfxu@zstu.edu.cn
› InstitutsangabenWe 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.
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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)-ones

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1706549.
  • Supporting Information


Publikationsverlauf

Eingereicht: 11. August 2020

Angenommen nach Revision: 23. September 2020

Artikel online veröffentlicht:
02. November 2020

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