Synlett 2022; 33(20): 2009-2012
DOI: 10.1055/a-1938-0643
letter

Transition-Metal-Free Synthesis of 3-Ethynylcoumarins by a DBU-Promoted Intramolecular Morita–Baylis–Hillman-Type Reaction/Dehydration/Isomerization Cascade

Shuolu Dai
a   Department of Chemistry, Zhejiang Sci-Tech University, Hangzhou, 310018, P. R. of China
,
Xiaoyu Gu
a   Department of Chemistry, Zhejiang Sci-Tech University, Hangzhou, 310018, P. R. of China
,
Zhen Wang
b   School of Pharmaceutical Sciences and Chongqing Key Laboratory of Natural Drug Research, Chongqing University, Chongqing, 401331, P. R. of China
,
Weijun Yao
a   Department of Chemistry, Zhejiang Sci-Tech University, Hangzhou, 310018, P. R. of China
› Author Affiliations
We thank the Natural Science Foundation of Zhejiang Province (Grant LTZ22B020002 and Grant LY20B020012) and Fundamental Research Funds for the Central Universities (2022CDJXY-025) for their financial support of this work.


Abstract

A transition-metal-free synthesis of 3-ethynylcoumarins from salicylaldehyde-derived alkynoates was developed involving a DBU-promoted intramolecular Morita–Baylis–Hillman-type reaction/dehydration/isomerization cascade. A wide variety of alkynoates were employed to deliver 3-ethynylcoumarins in moderate to good yields.

Supporting Information



Publication History

Received: 02 August 2022

Accepted after revision: 07 September 2022

Accepted Manuscript online:
07 September 2022

Article published online:
17 October 2022

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