19555-09-0

Upstream product

• 150-19-6 O-methylresorcine 
• 5813-48-9 Methanesulfenyl chloride 
• 624-92-0 Dimethyldisulphide 
• 837377-22-7 4-(allyloxy)-2-methoxy-1-(methylsulfanyl) benzene 

Downstream Products

• 19349-06-5 2-Methoxy-5-methylthio-p-benzochinon 
• 68721-75-5 Dimethyl-carbamic acid 3-methoxy-4-methylsulfanyl-phenyl ester 

Relevant academic research and scientific papers

NICOTINAMIDE DERIVATIVES USEFUL AS PDE4 INHIBITORS

This invention relates to nicotinamide derivatives of formula (I) and to pharmaceutical compositions containing, and the uses of such derivatives as PDE4 inhibitors wherein R7 is attached to the 3-or 4-position of the phenyl ring and is S(O)pR8, R8 is (C1-C4)alkyl optionally substituted by (C3-C6)cycloalkyl; m is 0 or 1; L is a (C3-C8)carbocyclic non-aromatic ring; and the remaining variables are as defined in the claims.

Phenyl heterocyclyl ethers

The invention relates to compounds of formula I

Diphenyl ether compounds useful in therapy

A compound of general formula (I), or pharmaceutically acceptable salts, solvates or polymorphs thereof; wherein; R1 and R2, which may be the same or different, are hydrogen, C1-C6alkyl, (CH2)m(C3-C6cycloalkyl) wherein m =0, 1, 2 or 3, or R1 and R2 together with the nitrogen to which they are attached form an azetidine ring; each R3 is independently CF3, OCF3, C1-4alkylthio or C1-C4alkoxy; n is 1, 2 or 3; and R4 and R5, which may be the same or different, are: A-X, wherein A =—CH=CH— or —(CH2)p— where p is 0, 1 or 2; X is hydrogen, F, Cl, Br, I, CONR6R7,SO2NR6R7, SO2NHC(=O)R6, OH, C1-4alkoxy, NR8SO2R9, NO2, NR6R11, CN, CO2R10, CHO, SR10, S(O)R9 or SO2R10 R6, R7, R and R10 which may be the same or different, are hydrogen or C1-6alkyl optionally substituted independently by one or more R12; R9 is C1-6 alkyl optionally substituted independently by one or more R12; R11 is hydrogen, C1-6 alkyl optionally substituted independently by one or more R12, C(O)R6, CO2R9, C(O)NHR6 or SO2NR6R7; R12 is F, OH, CO2H, C3-6cycloalkyl, NH2, CONH2, C1-6alkoxy, C1-6alkoxycarbonyl or a 5- or 6-membered heterocyclic ring containing 1, 2 or 3 heteroatoms selected from N, S and O optionally substituted independently by one or more R13; or R6 and R7, together with the nitrogen to which they are attached, form a 4-, 5- or 6-membered heterocyclic ring optionally substituted independently by one or more R13; or a 5- or 6-membered heterocyclic ring containing 1, 2 or 3 heteroatoms selected from N, S and O, optionally substituted independently by one or more R13; wherein R13 is hydroxy, C1-C4alkoxy, F, C1-C6alkyl, haloalkyl, haloalkoxy, —NH2, —NH(C1-C6alkyl) or —N(C1-C6alkyl)2; wherein when R1 and R2 are methyl, R4 and R5 are hydrogen and n is 1, R3is not a —SMe group para to the ether linkage linking rings A and B.

Direct Lithiation of Alkoxyphenols: Metalation vs Demethylation. An Experimental and Theoretical (MNDO) Study

The direct lithiation of simple alkoxyphenols has been studied both from a theoretical and an experimental viewpoint.Efficient lithiations were achieved by using a 2:1 tBuLi-tBuOLi mixture (LICLIOR) in THF at room temperature.In most cases alkoxy groups are responsible for the regioselectivity observed, although for the case of 2-methoxyphenol both the OMe and OLi groups actually act as ortho-directing groups during lithiation.Demethylation has been shown to be a common side reaction of lithiation of phenolic or nonphenolic alkoxy aromatics.MNDO calculations provide good support for all the experimental observations.Thus, lithiation and demethylation are shown to be competing pathways, the former being kinetically favored whereas the latter leads to the thermodynamically more stable compounds.Calculations also show that the so-called geminal demethylations are more favored processes than the alternative vicinal demethylations.Moreover, MNDO allows the measurement of the extent of agostic activation of the ortho hydrogens with respect to the OMe and OLi groups involved in lithiation.Finally, MNDO nicely predicts the important role of reaction temperature in successful direct lithiation of simple alkoxyphenols.