51786-56-2Relevant articles and documents
Microwave-assisted Pechmann reaction on P2O5/molecular sieves. Application to the preparation of 4-substituted coumarins
Shockravi, Abbas,Valizadeh, Hassan,Heravi, Majid M.
, p. 2835 - 2841 (2002)
4-Substituted coumarins were efficiently and rapidly synthesised via Pechmann condensation of phenols with ethyl acetoacetate catalyzed by P2O5/molecular sieves in satisfactory yields.
B(C6F5)3-catalyzed synthesis of coumarins via Pechmann condensation under solvent-free conditions
Prajapti, Santosh Kumar,Rao, S. Prakash
, p. 469 - 473 (2021/03/26)
Tris(pentafluorophenyl)borane [B(C6F5)3] catalyzed simple, efficient and environmentally benign protocol has been developed for the Pechmann condensation using variety of phenols and β-ketoesters under solvent-free conditions to afford coumarin derivatives. The present protocol displayed significant advantages such as low catalyst loading, short reaction time, mild reaction conditions, low toxicity, easy work-up, high yields, and compatibility with other functional groups. In addition, it is a convenient, clean, and fast alternative approach for synthesizing variety of coumarin derivatives. Moreover, the applicability of this method towards large-scale synthesis demonstrated its suitability for the industrial application. Graphic abstract: [Figure not available: see fulltext.]
Synthesis, Cytotoxicity and Antimicrobial Evaluation of New Coumarin-Tagged β-Lactam Triazole Hybrid
Awolade, Paul,Cele, Nosipho,Dhawan, Sanjeev,Jonnalagadda, Sreekantha B.,Kaur, Mandeep,Kisten, Prishani,Pillay, Ashona-Singh,Saha, SouravTaru,Singh, Parvesh
, (2020/01/24)
A series of coumarin-tagged β-lactam triazole hybrids (10a–10o) were synthesized and tested for their cytotoxic activity against MDA-MB-231 (triple negative breast cancer), MCF-7 (estrogen receptor positive breast cancer (ER+)) and A549 (human lung carcinoma) cancer cell lines including one normal cell line, HEK-293 (human embryonic kidney). Two compounds 10b and 10d exhibited substantial cytotoxic effect against MCF-7 cancer cell lines with IC50 values of 53.55 and 58.62 μm, respectively. More importantly, compounds 10b and 10d were non-cytotoxic against HEK-293 cell lines. Structure–activity relationship (SAR) studies suggested that the nitro and chloro group at the C-3 position of phenyl ring are favorable for anticancer activity, particularly against MCF-7 cell lines. Furthermore, antimicrobial evaluation of these compounds revealed modest inhibition of examined pathogenic strains with compounds 10c and 10i being the most promising antimicrobial agents against Pseudomonas aeruginosa and Candida albicans, respectively.
Recyclable cellulose nanocrystal supported Palladium nanoparticles as an efficient heterogeneous catalyst for the solvent-free synthesis of coumarin derivatives via von Pechmann condensation
Mirosanloo, Atieh,Zareyee, Daryoush,Khalilzadeh, Mohammad A.
, (2018/10/15)
2-Amino pyrimidine nanocellulose-supported Palladium nanoparticles (CNC-AMPD-Pd) as a novel bio supported nanocatalyst was prepared and characterized by ICP-AES, FT-IR, XRD, SEM, TEM, TGA and EDX techniques. The nanocatalyst demonstrated outstanding performance in Pechmann condensation between different substituted phenols and ethyl acetoacetate to obtain coumarin derivatives in good to excellent yields. The catalyst is easily recycled and reused without loss of the catalytic activity. The combined merits of reusable catalyst and solvent-free reaction conditions make the condensation with safe operation, no leaching of pd into environment, low pollution, rapid access to products and simple workup.
