Synthesis of 4-Aryldihydrocoumarins via a Sequential Michael Addition–Lactonization Route

2021 ◽  
Vol 08 ◽  
Author(s):  
Anshu Kumar Sinha ◽  
Chandra Mohan Srivastava ◽  
Gyandshwar K. Rao ◽  
Manvika Karnatak ◽  
Ved Prakash Verma ◽  
...  

Background: Coumarin and its derivatives have attracted the attention of synthetic chemists due to their importance in pharmaceutical and medicinal chemistry. The acid-catalyzed cyclization route constitutes the method of choice to access these important compounds. Objective: In this paper, we have discussed the synthesis of 4-aryldihydrocoumarins via a one-pot p-sulfonic acid calix[4]arene catalyzed reaction. Method: The easily prepared calix[4]arene derivative catalyzes a sequential reaction involving Michael addition followed by intramolecular lactonization to afford the title compound in decent yield. Results: The described methodology is devoid of any metal salt, thus making it a very appealing protocol to safely produce dihydrocoumarins of pharmacological importance. Conclusion: The easy recovery, non-toxicity, and reusability of the catalytic system are some of the other advantages of our procedure. In addition, the catalyst efficiency is not compromised after its successive use in reactions.

ChemInform ◽  
2009 ◽  
Vol 40 (11) ◽  
Author(s):  
Li-Tao An ◽  
Xiao-Hua Lu ◽  
Fei-Qing Ding ◽  
Wen-Qing Jiang ◽  
Jian-Ping Zou

Tetrahedron ◽  
2013 ◽  
Vol 69 (2) ◽  
pp. 647-652 ◽  
Author(s):  
Ningning Wang ◽  
Shuying Cai ◽  
Chao Zhou ◽  
Ping Lu ◽  
Yanguang Wang

RSC Advances ◽  
2014 ◽  
Vol 4 (108) ◽  
pp. 62817-62826 ◽  
Author(s):  
Dan Zhu ◽  
Jing Sun ◽  
Chao-Guo Yan

One pot sequential reaction of generation of β-enamino ester, Michael addition and Pictet–Spengler reaction.


ChemInform ◽  
2010 ◽  
Vol 41 (32) ◽  
pp. no-no
Author(s):  
Han-Feng Cui ◽  
Ke-Yan Dong ◽  
Jing Nie ◽  
Yan Zheng ◽  
Jun-An Ma

2019 ◽  
Vol 20 (1) ◽  
pp. 60
Author(s):  
Muhammad Siddiq Maarop ◽  
Fatin Nur Ain Abdul Rashid ◽  
Mohd Fazli Mohammat ◽  
Zurina Shaameri ◽  
Saiful Azmi Johari ◽  
...  

A library of some novel classes of pyrano[2,3-c]pyrazole-3-carboxylates was synthesized by employing uncatalyzed domino four-component reaction using diethyloxaloacetate, hydrazine hydrate, aldehydes and malononitrile in refluxing of ethanol-acetic acid solvent systems. Series of domino reactions involving of pyrazolone formation, Michael addition, and Thorpe-Ziegler cyclization reaction managed to produce the cyclized products from moderate to excellent yield. This protocol provides a reliable, general and salient procedure for the title compound using a one-pot approach. Preliminary biological screening unveiled limited potentials of this class of compounds for antimicrobial lead compound due to its limited solubility properties.


2020 ◽  
Vol 7 (1) ◽  
pp. 53-63 ◽  
Author(s):  
Yumeng Yuan ◽  
Guoshuai Pan ◽  
Xiaofeng Zhang ◽  
Qiufeng Huang

An unprecedented one-pot C–H olefination/aza-Michael addition tandem process has been developed for the synthesis of pyrrolo[3,2,1-de]phenanthridines from 7-phenylindoles and alkenes using a [Cp*RhCl2]2/AgOAc/Me4NOAc catalytic system.


2020 ◽  
Vol 44 (22) ◽  
pp. 9546-9556
Author(s):  
Zunming Sun ◽  
Fuyao Liu ◽  
Xinyue Yang ◽  
Xianpei Huang ◽  
Mengmeng Zhang ◽  
...  

Acid/base bi-functional polymeric materials were prepared using physically mixed porous polymers P(DVB-VBS) with sulfonic acid and P(DVB-VBA) with amino groups for various cascade reactions.


ChemInform ◽  
2016 ◽  
Vol 47 (3) ◽  
Author(s):  
Jagatheeswaran Kothandapani ◽  
Asaithampi Ganesan ◽  
Subramaniapillai Selva Ganesan

2017 ◽  
Vol 90 ◽  
pp. 106-110 ◽  
Author(s):  
Xiaolan Feng ◽  
Lijun Wang ◽  
Xiandong Yao ◽  
Huaping Dong ◽  
Xiaoxia Wang ◽  
...  

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