3722-73-4

Upstream product

• 13030-21-2 3-(m-methylphenoxy)propan-1-ol 
• 325147-40-8 3-(2-bromo-4-methylphenyl)propanol 
• 2445-83-2 7-methylcoumarin 
• 698-27-1 4-methylsalicylaldehyde 
• 1154740-75-6 C₁₂H₁₄O 
• 1082192-06-0 2-(allyloxy)-4-methylbenzaldehyde 
• 5406-39-3 3-(4-methylphenyl)propanol 
• 71838-16-9 3-bromo-4-iodotoluene 
• 325147-50-0 3-(2-bromo-4-methylphenyl)propanal 
• 90926-15-1 2-(3-hydroxypropyl)-5-methylphenol 
• 18385-88-1 7-methyl-2H-chromene 
• 108-39-4 3-methyl-phenol 

Relevant academic research and scientific papers

An efficient preparation of chroman derivatives from 3-aryl-1-propanols and related compounds with 1,3-diiodo-5,5-dimethylhydantoin under irradiation conditions

Treatment of various 3-aryl-1-propanols with 1,3-diiodo-5,5- dimethylhydantoin (DIH) in ethyl acetate or 1,2-dichloroethane under irradiation with a tungsten lamp gave the corresponding chroman derivatives in good to moderate yields. The present reaction proceeds via the initial formation of an alkoxyl radical and the radical cyclization onto the aromatic ring, followed by the oxidation of the formed radical intermediate with DIH to provide the chroman derivative. The same treatment of o-biphenyldimethylcarbinol, o-phenylbenzoic acid, and o-alkylbenzoic acids with DIH provided the corresponding chroman derivatives and lactone derivatives in good yields, respectively. Georg Thieme Verlag Stuttgart - New York.

INHIBITORS OF HUMAN IMMUNODEFICIENCY VIRUS REPLICATION

Compounds of formula (I): wherein R4, R6 and R7 are defined herein, are useful as inhibitors of HIV replication.

INHIBITORS OF HUMAN IMMUNODEFICIENCY VIRUS REPLICATION

Compounds of formula (I): wherein c, X, Y, R2, R4 and R5 are defined herein, are useful as inhibitors of HIV replication.

INHIBITORS OF HUMAN IMMUNODEFICIENCY VIRUS REPLICATION

The present invention relates to compounds of formula (I) wherein c, X, Y, R2, R3, R4 and R6 are as defined herein, compositions and uses thereof for treating human immunodeficiency virus (HIV) infection. In particular, the present invention provides novel inhibitors of HIV integrase, pharmaceutical compositions containing such compounds and methods for using these compounds in the treatment of HIV infection

INHIBITORS OF HUMAN IMMUNODEFICIENCY VIRUS REPLICATION

Compounds of formula I : wherein c, R2, R3, R4, R5, R6, R7 and R8 are defined herein, are useful as inhibitors of HIV replication.

Copper(I)-catalyzed aryl bromides to form intermolecular and intramolecular carbon-oxygen bonds

(Chemical Equation Presented) A highly efficient Cu-catalyzed C-O bond-forming reaction of alcohol and aryl bromides has been developed. This transformation was realized through the use of copper(I) iodide as a catalyst, 8-hydroxyquinoline as a ligand, and K3PO4 as a base. A variety of functionalized substrates were found to react under these reaction conditions to provide products in good to excellent yields.

Palladium-catalyzed intramolecular C-O bond formation

A number of oxygen heterocycles were synthesized using the palladium-catalyzed intramolecular etherification of aryl halides by employing di-tert-butylphosphinobiaryl ligands. The reaction proceeds under mild conditions using weak bases such as Cs2CO3 or K3PO4. A variety of functional groups are tolerated in the reaction, and enantioenriched alcohols can be coupled without erosion of optical purity. The mildness of the reaction conditions allows for the use of polyfunctionalized substrates. This method was used as the key step in the synthesis of MKC-242, an antidepressant currently in clinical trials. The synthesis of MKC-242 was achieved in 40% overall yield from commercially available sesamol and acrylonitrile.

Reactions of γ-arylalkanols via aryl radical cation and alkoxyl radical intermediates. Part 3. Reactions of 3-arylprop-1-yl hydroperoxides with iron(II) in the presence of copper(II)

A strategy for comparing the 1,5- and 1,6-cyclisation reactions of 3-phenylpropan-1-oxyl radicals is described.Iron(II)-catalysed reduction of 3-(p-methylphenyl)prop-1-yl hydroperoxide and its para-chloro and para-methoxy-substituted analogues, carried out in the presence of copper(II), has been found to give in each case the appropriate para-substituted 3-phenylpropan-1-ol, 3-phenylpropanal and a low yield of a mixture of isomeric 6- and 7-substituted chromans.The alcohols are proposed to form via reduction of either the hydroperoxide or the resulting alkoxyl radical or its cyclised intermediates, and the aldehydes as a result of rearrangement of the alkoxyl radical to an α-hydroxy alkyl radical which subsequently undergoes oxidation.The 7-substituted chromans, which arise directly from 1,6-cyclisation of the alkoxyl radical, were found to dominate the 6-substituted isomers which result from rearrangement of 1,5-cyclised intermediates.This effect is attributed to inefficient interception of the 1,5-cyclised radical intermediate which permits equilibration to the thermodynamically more stable 1,6-cyclised radical isomer to occur.The effect of pH on the reactions has been investigated and although no products typical of the intermediacy of aryl radical cations were detected (even under highly acidic conditions), the formation of such intermediates cannot be excluded.Semiempirical MO calculations have been carried out (at the PM3 level of approximation) on a series of model compounds, yielding results which have clarified our understanding of the effect of substituents on the stabilities of the various intermediates arising from the cyclisation reactions of 3-phenylpropan-1-oxyl radicals.Furthermore, these calculations have supported our assumptions regarding the probability and specificity of rearrangements of the spirodienyl intermediates.

Cyclisation of 3-(p-Methylphenyl)propan-1-ol via its Alkoxyl Radical and Aryl Radical Cation Intermediates. A Comparison of Regioselectivities

Evidence is presented that 3-(p-methylphenyl)propan-1-ol 5 undergoes competing 1,5- and 1,6-cyclisation via both its aryl radical cation 6 and alkoxy radical 7 intermediates.Variations in both product yields and regioselectivities of cyclisation with pH are observed, with evidence of significant differences between the two intermediates.