69976-30-3Relevant academic research and scientific papers
Three-component coupling using arynes and DMF: Straightforward access to coumarins via ortho-quinone methides
Yoshida, Hiroto,Ito, Yu,Ohshita, Joji
, p. 8512 - 8514 (2011)
ortho-Quinone methides, arising from a formal [2+2] cycloaddition between arynes and DMF, were found to facilely undergo a [4+2] cycloaddition with ester enolates or ketenimine anions to produce diverse coumarins in a straightforward manner. The Royal Society of Chemistry 2011.
Rh-Catalyzed aldehydic C-H alkynylation and annulation
Ramakrishna, Boddu S.,Rao, Maddali L. N.
, p. 1402 - 1411 (2020/03/03)
Novel Rh-catalyzed aldehydic C-H bond alkynylation and annulation for the in situ synthesis of chromones and aurones are described. It involves the sequential aldehyde C-H bond alkynylation of salicylaldehyde with in situ generated 1-bromoalkyne from 1,1-
Visible-light-driven copper-catalyzed aerobic oxidative cascade cyclization of N-tosylhydrazones and terminal alkynes: Regioselective synthesis of 3-arylcoumarins
Ragupathi, Ayyakkannu,Sagadevan, Arunachalam,Charpe, Vaibhav Pramod,Lin, Chun-Cheng,Hwu, Jih-Ru,Hwang, Kuo Chu
supporting information, p. 5151 - 5154 (2019/05/10)
We present the first example of sustainable, intuitive, highly regioselective, visible-light-driven copper catalyzed aerobic oxidative cascade cyclization of N-tosylhydrazones with terminal alkynes for the preparation of 3-arylcoumarins at room temperature. This operationally simple methodology has been successfully applied to a wide range of N-tosylhydrazones and alkynes (49 examples), and proceeds well to afford biologically active compounds, such as monoamine oxidase B (MAO-B) inhibitor and horseradish peroxidase (HRP) inhibitor, in satisfactory yields under mild conditions. Furthermore, mechanistic studies suggest that the reaction proceeds via a copper(ii)-superoxo or -peroxo complex mediated oxidative annulation of terminal alkynes, as evidenced by 18O2 isotopic-labelling experiments.
3-phenylcoumarins as inhibitors of HIV-1 replication
Olmedo, Dionisio,Sancho, Rocio,Bedoya, Luis M.,Lopez-Perez, Jose L.,Del Olmo, Esther,Munoz, Eduardo,Alcami, Jose,Gupta, Mahabir P.,Feliciano, Arturo San
, p. 9245 - 9257 (2013/01/14)
We have synthesized fourteen 3-phenylcoumarin derivatives and evaluated their anti-HIV activity. Antiviral activity was assessed on MT-2 cells infected with viral clones carrying the luciferase gene as reporter. Inhibition of HIV transcription and Tat function were tested on cells stably transfected with the HIV-LTR and Tat protein. Six compounds displayed NF-κB inhibition, four resulted Tat antagonists and three of them showed both activities. Three compounds inhibited HIV replication with IC50 values 25 μM. The antiviral effect of the 4-hydroxycoumarin derivative 19 correlates with its specific inhibition of Tat functions, while compound 8, 3-(2-chlorophenyl) coumarin, seems to act through a mechanism unrelated to the molecular targets considered in this research.
A convenient one-pot synthesis of 4-methyl-3-phenyl-, 3-aryl- and 3-aryl-4-phenylcoumarins
Kamat, Shrivallabh P.,D'Souza, Asha M.,Paknikar, Shashikumar K.,Beauchamp, Philip S.
, p. 242 - 246 (2007/10/03)
Thermal condensation of 2′-hydroxyacetophenones 1a-e with phenylacetic acid 2a in refluxing diphenyl ether gives 4-methyl-3-phenylcoumarins 3a-e. Similarly, reaction of 2-hydroxybenzaldehydes 1f-m and 2-hydroxybenzo-phenones 1n-p with phenylacetic acids 2a-d gives the corresponding 3-arylcoumarins 3f-m and 3-aryl-4-phenylcoumarins 3n-p respectively. Formation of esters 4 and 5 and benzofuran 6 is also observed.
