35817-28-8

Upstream product

• 68903-74-2 3-iodo-4-phenoxy-2H-chromen-2-one 
• 1076-38-6 4-hydroxy[1]benzopyran-2-one 
• 108-95-2 phenol 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 938-40-9 4-Bromo-2H-1-benzopyran-2-one 
• 200055-89-6 4-(4-toluenesulfonyloxy)coumarin 
• 98-80-6 phenylboronic acid 
• 109363-83-9 6H-<1>benzopyrano<4,3-b><1,4>benzoxanthiin-6-one 

Downstream Products

• 100914-71-4 3-chloro-4-phenoxy-2-coumarin 
• 4222-13-3 3,3-diphenyl-1-(2-hydroxyphenyl)-2-propen-1-one 
• 491-37-2 2,3-dihydro-4H-1-benzopyran-4-one 
• 479-12-9 coumestan 

Relevant academic research and scientific papers

An efficient route to 4-aryloxycoumarins via one-pot reactions of 4-hydroxycoumarins with hypervalent iodine reagents

Highly efficient reactions of 4-hydroxycoumarin with hypervalent iodine reagents under mild conditions are described, which give rise to 4-aryloxycoumarins in good to excellent yields.

Copper(II) acetate catalyzed ullmann-type C-O coupling reaction of phenols with 4-tosylcoumarin

A copper(II) acetate mediated Ullmann-type reaction of phenols with 4-tosylcoumarin for the synthesis of 4-aryloxycoumarins is reported. The method has some attractive features such as operational simplicity, moderate to good yields, and the use of ligand-free copper(II) acetate as a green and stable catalyst.

Mechanistic studies on the palladium-catalyzed cross-dehydrogenative coupling of 4-phenoxy-2-coumarins: Experimental and computational insights

Delineating the mechanistic features of C-H activation in aryl-heteroaryl coupling is an important step in the design of selective, catalytic processes. Herein we use the intramolecular dehydrogenative coupling of 4-phenoxy-2-coumarins as a model study. Computational results and experimental studies suggest that CMD is operative in the cleavage of both C-H bonds, and that the heteroaryl C-H is cleaved initially.

One-pot two-step synthesis of 3-iodo-4-aryloxy coumarins and their Pd/C-catalyzed annulation to coumestans

An efficient protocol for the synthesis of various coumestans from the intramolecular annulation of 3-iodo-4-aryloxy coumarins through C-H activation has been developed. When 3-iodo-4-aryloxy coumarins were treated with 10% Pd/C (0.3 mol% Pd) in the presence of sodium acetate, the corresponding coumestans were produced in good to excellent yield. Reusability of the palladium catalyst was investigated in up to three consecutive cycles and it was found that the yield of the reaction was almost unaltered. Sequential iodination and O-arylation of 4-hydroxy coumarins leading to the 3-iodo-4-aryloxy coumarins were also achieved in a one-pot two-step process starting from aryl iodides in high yield. Pivalic acid was revealed to be the most effective additive for the later method to produce 3-iodo-4-phenoxy coumarins. Different functional groups bearing electron-donating as well as withdrawing groups are also tolerant to the reaction conditions.

Pd/Indanone-Based Ligands: An Efficient Catalyst System for Ullmann-Type, Suzuki-Miyaura, and Mizoroki-Heck Cross-Coupling Reactions with Aryl Tosylates and Aryl Halides

2-Hydroxyindan-1-ones have been efficiently synthesized and successfully applied as ligands in Pd-catalyzed Ullmann type, Suzuki-Miyaura, and Mizoroki-Heck cross-coupling reactions with aryl tosylates and aryl halides. The ligands are air- and moisture-stable and have shown high catalytic activity with Pd(OAc) 2 in these cross-coupling reactions. The system tolerates a variety of functional groups in the product and can be re-used at least three times with maximum efficiency..

Cyclization of 4-Phenoxy-2-coumarins and 2-Pyrones via a Double C-H Activation

Aryl-heteroaryl coupling via double C-H activation is a powerful transformation that avoids the installation of activating groups. A double C-H activation of privileged biological scaffolds, 2-coumarins and 2-pyrones, is reported. Despite the rich chemistry of these molecular frameworks, the yields are very good. Excellent regioselectivity was achieved on the pyrones. This methodology was applied to the synthesis of flemichapparin C in three steps. Isotope effect experiments were carried out, and a mechanism is proposed.

Intramolecular Direct Arylation of 3-Halo-2-pyrones and 2-Coumarins

Direct arylation represents a favorable alternative to traditional cross-coupling and has found widespread use with simple aryls and robust heterocycles. Herein a direct arylation protocol has been optimized and applied to 2-pyrones, which are delicate an

Expedient synthesis of biologically potent aryloxycoumarins and (aryloxyimino)ethylcoumarins via copper(II)-promoted chan-lam coupling reaction

A convenient protocol for the efficient synthesis of aryloxycoumarins and (aryloxyimino)ethylcoumarins is described. The synthetic route developed involves the Cu-promoted C-O and N-O coupling reactions from readily available hydroxycoumarin and (hydroxyi

SPIROCYCLIC MEISENHEIMER COMPLEXES. XXX. THE FORMATION OF ANIONIC SPIRO-? COMPLEXES IN THE 3-NITRO-4-(2-HYDROXYPHENYLTHIO)-6-R-2H-BENZOPYRAN-2-ONE SYSTEM AND THE INTRAMOLECULAR ORTHO-CYCLIZATION ACCOMPANIED BY A SMILES REARRANGEMENT

The reaction of 3-nitro- and 3,6-dinitro-4-chloro-2H-1-benzospiran-2-ones with 2-mercaptophenol gives 3-nitro- and 3,6-dinitro-4-(2-hydroxyphenylthio)-2H-1-benzopyran-2-ones.In the presence of triethylamine the products give anionic spiro complexes of the