65548-47-2

Upstream product

• 21785-09-1 7-methoxyflavanone 
• 673-22-3 2-Hydroxy-4-methoxybenzaldehyde 
• 4363-35-3 Dihydroxy-styryl-boran 
• 588-72-7 [(E)-2-bromoethenyl]benzene 
• 678554-43-3 C₁₅H₁₆N₂O₄S 
• 1255508-81-6 2-ethoxy-7-methoxy-2H-chromene 
• 98-80-6 phenylboronic acid 
• 52923-29-2 1-(2-hydroxy-4-methoxyphenyl)-3-phenylprop-2-en-1-one 
• 552-41-0 1-(2-hydroxy-4-methoxyphenyl)ethanone 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 

Relevant academic research and scientific papers

Glycerol as an efficient medium for the Petasis borono-mannich reaction

The multicomponent Petasis borono-Mannich (PBM) reaction is a useful tool for the preparation of complex molecules in a single step from boronic acids, aldehydes/ketones, and amines. Here, we describe the use of glycerol in the PBM reaction of salicylalde

Palladium-catalyzed coupling of N-tosylhydrazones and β-bromostyrene derivatives: New approach to 2H-chromenes

2H-Chromene is an important structural motif that exists in natural products and non-natural compounds possessing interesting biological activities. In this investigation, a highly efficient approach toward 2H-chromenes has been developed based on palladium-catalyzed coupling of N-tosylhydrazones and β-bromostyrenes. The mechanism of this reaction is proposed that involves the formation of vinyl palladium by carbene migratory insertion and the intramolecular nucleophilic substitution. This journal is

Nickel-catalyzed cross-coupling of chromene acetals and boronic acids

A modular and highly efficient protocol for the synthesis of 2-aryl- and heteroaryl-2H-chromenes is described. Under base-free conditions, readily accessible 2-ethoxy-2H-chromenes undergo Csp3-O activation and C sp3-C bond formation in the presence of an inexpensive nickel catalyst and boronic acids. This new strategy enables broad access to 2-substituted-2H-chromenes and has been applied to the late-stage incorporation of complex molecules, including the pharmaceuticals loratidine and indomethacin methyl ester.

Rhodium-catalyzed cyclopropanations of 2-aryl-2H-chromenes with dialkyl malonate esters. A comparison of α-diazo derivatives and phenyliodonium ylides

Rhodium-catalyzed reactions of 2-aryl-substituted 2H-chromenes with α-diazo esters prepared from dimethyl and tert-butyl methyl malonates were investigated, and the results were compared with reactions carried out with phenyliodonium ylides prepared from the same esters. The phenyliodonium ylide prepared from dimethyl malonate was found to give superior yields of cyclopropane products compared to the corresponding α-diazo equivalent. However, this result was reversed with tert-butyl methyl malonate when Rh 2(S-TBSP)4 was used to decompose the diazo compound. All reactions gave 1,1-cyclopropane diesters as single diastereomers.

Synthesis and antimalarial evaluation of novel benzopyrano[4,3-b]benzopyran derivatives

7-Methoxyflavenes and 5,7,8-trimethoxyflavenes were found to undergo stereoselective acid-catalyzed rearrangement to generate the benzopyrano[4,3-b]benzopyran ring system present in the natural product, dependensin. Dependensin and its analogs were subjected to antimalarial growth inhibition assays against Plasmodium falciparum and found to have IC 50 values ranging between 1.9 and 3.9 μM.

Synthesis and structure of flavan-4-ols and 4-methoxyflavans as new potential anticancer drugs

Reduction of a series of substituted flavanones afforded synthetic access to flavan-4-ols and was followed for some of them by an S(N)2-type acid-catalysis in methanol to provide 4-methoxyflavans. The stereochemistry of these compounds was established by 1H and 13C NMR data. Flavan-4-ols and 4-methoxyflavans have been resolved into enantiomers which are being evaluated as anticancer drugs. (C) 2000 Elsevier Science Ltd.