86795-49-5

Upstream product

• 1076-38-6 4-hydroxy[1]benzopyran-2-one 
• 27126-76-7 [hydroxy(tosyloxy)iodo]benzene 
• 4438-85-1 3H-chromene-2,4-dione 
• 3240-34-4 [bis(acetoxy)iodo]benzene 

Downstream Products

• 1786-05-6 4-hydroxy-3-phenylcoumarin 
• 26151-95-1 4-hydroxy-3-(4-methoxyphenyl)-2H-chromen-2-one 
• 1143505-49-0 2-(4-(tert-butyl)phenyl)-4H-furo[3,2-c]chromen-4-one 
• 68903-74-2 3-iodo-4-phenoxy-2H-chromen-2-one 
• 81-81-2 warfarin 
• 1605320-01-1 3-benzyl-2H-pyrano[3,2-c]chromene-2,5(6H)-dione 
• 2288-98-4 <2>benzopyrano<4,3-c><1>benzopyran-5,12-dione 

Relevant academic research and scientific papers

Iodonium Ylides as Carbene Precursors in Rh(III)-Catalyzed C-H Activation

The rhodium(III)-catalyzed coupling of C-H substrates with iodonium ylides has been realized for the efficient synthesis of diverse cyclic skeletons, where the iodonium ylides have been identified as efficient and outstanding carbene precursors. The reaction systems are applicable to both sp2 and sp3 C-H substrates under mild and redox-neutral conditions. The catalyst loading can be as low as 0.5 mol % in a gram-scale reaction. Representative products exhibit cytotoxicity toward human cancer cells at nanomolar levels.

Hypervalent Iodine(III)-Mediated Tosyloxylation of 4-Hydroxycoumarins

An efficient approach was developed for synthesis of 3-tosyloxy-4-hydroxycoumarins under mild conditions by using Koser's reagents. The reaction tolerated various functional groups, and the products served as useful aromatic building blocks. Additionally, a plausible mechanism via iodonium ylide was proposed, and the oral anticoagulant Warfarin was synthesized in good yield.

Support-Free Pd3Co NCs as an Efficient Heterogeneous Nanocatalyst for New Organic Transformations of C?C Coupling Reactions

A support-free heterogeneous Pd3Co nanostructured composite (NC), synthesized through a hydrothermal route, acted as an effective catalytic system in multivariate Heck-, Sonogashira-, and Suzuki-type coupling reactions of iodonium ylides. The XPS analysis of the bimetallic Pd3Co NCs confirmed the elemental composition as 75 % palladium and 25 % cobalt. Furthermore, high-resolution (HR) TEM analysis confirmed the spherical morphology of the Pd3Co bimetallic nanoparticles. The average diameter of the NCs is 14.8 nm. The coupling reaction proceeded through the generation of α-iodoenones with simultaneous migration of the phenyl group, thereby giving a scaffold with higher atom economy. The heterogeneous Pd3Co NCs were recycled and reused without any significant change in catalytic ability for up to five reaction cycles. The high concentration of Pd and association of cobalt into the lattice of palladium appears to enhance its catalytic ability for the diverse coupling reactions in comparison with its monometallic counterparts as well as with bimetallic NCs with a comparatively lesser amount of Pd.

Hydroxycoumarins as selective MAO-B inhibitors

A series of 3-aryl-4-hydroxycoumarin derivatives was synthesized with the aim to find out the structural features for the MAO inhibitory activity and selectivity. Methoxy and/or chloro substituents were introduced in the 3-phenyl ring, whereas the positio

Antitrypanosomal and antioxidant properties of 4-hydroxycoumarins derivatives

In the present communication we prepared a series of six 4-hydroxycoumarin derivatives, isosters of quercetin, recognized as an antioxidant natural compound, with the aim of evaluating the antitrypanosomal activity against Trypanosoma cruzi, the parasite

Synthesis and cytotoxic activity of non-naturally substituted 4-oxycoumarin derivatives

Coumarins are a large family of natural and synthetic compounds exerting different pharmacological effects, including cytotoxic, anti-inflammatory or antimicrobial. In the present communication we report the synthesis of a series of 12 diversely substituted 4-oxycoumarin derivatives including methoxy substituted 4-hydroxycoumarins, methyl, methoxy or unsubstituted 3-aryl-4-hydroxycoumarins and 4-benzyloxycoumarins and their anti-proliferative effects on breast adenocarcinoma cells (MCF-7), human promyelocytic leukemia cells (HL-60), human histiocytic lymphoma cells (U937) and mouse neuroblastoma cells (Neuro2a). The most potent bioactive molecule was the 4-hydroxy-5,7- dimethoxycoumarin (compound 1) which showed similar potency (IC50 0.2-2 μM) in all cancer cell lines tested. This non-natural product reveals a simple bioactive scaffold which may be exploited in further studies.

COMPOUNDS USEFUL AS ANTIVIRAL AGENTS, COMPOSITIONS, AND METHODS OF USE

Novel 3-N-cycloalkyl-5-substituted-2-thioxothiazolidin-4-one derivatives that are effective for use in treating viral infections are described. Also described are pharmaceutical compositions comprising the 3-N-cycloalkyl-5-substituted-2-thioxothiazolidin-

Phenyliodonium zwitterion as an efficient electrophile in the palladium-catalyzed suzuki-type reaction: A novel method for the synthesis of 3-aryl-4-hydroxycoumarins

equation presented A palladium-catalyzed coupling reaction of phenyliodonium zwitterions with aryl boronic acids has been developed. The unique characteristics of the mild reaction conditions and convenient synthetic accessibility of phenyliodonium zwitterions make this method a valuable tool for generating diversified 3-aryl-4-hydroxycoumarins.

A new and efficient synthesis of coumestan and coumestrol

4-Aryloxy-3-iodocoumarins (4-aryloxy-3-iodo-2H-1-benzopyran-2-one), 4a-c, which are readily available by known procedures starting from 4-hydroxycoumarins 1 a,b and diacetoxyiodobenzenes 2a-c; are cyclized with palladium chloride in triethylamine to yield the coumestanes (6H-benzofuran[3,2-c][1]benzopyran-6-ones) 5a-c.

IODONIUM DERIVATIVES OF β-DICARBONYL COMPOUNDS. XXIII. SYNTHESIS AND PROPERTIES OF IODONIUM DERIVATIVES OF 4-HYDROXYCOUMARIN

The 3-aryliodonio-4-hydroxycoumarin betaines were obtained by the reaction of 4-hydroxycoumarin with (diacetoxyiodo)benzene and 4-methoxy(diacetoxyiodo)benzene in acetone solution.When heated, they form the products from intramolecular arylation, i.e., 3-