54393-21-4Relevant articles and documents
Compounds for modulating TRPV3 function
-
Page/Page column 43-44, (2010/11/28)
The present application relates to compounds and methods for treating pain and other conditions related to TRPV3.
Siloxane-Based Cross-Coupling of Bromopyridine Derivatives: Studies for the Synthesis of Streptonigrin and Lavendamycin
McElroy, William T.,DeShong, Philip
, p. 4779 - 4782 (2007/10/03)
(Equation Presented) Highly functionalized 4-bromopyridines were prepared and found to undergo fluoride-promoted, Pd-catalyzed cross-coupling with aryltrialkoxy-silanes to give sterically demanding biaryls. The 3-nitro-4-bromopyridine derivative coupled i
Enantioselective hydrogenation of tetrasubstituted olefins of cyclic β-(acylamino)acrylates
Tang, Wenjun,Wu, Shulin,Zhang, Xumu
, p. 9570 - 9571 (2007/10/03)
Hydrogenation of a series of cyclic β-(acylamino)acrylates with tetrasubstituted olefins has been accomplished successfully with the use of Ru catalysts with chiral biaryl ligands such as C3-TunaPhos, and up to over 99% ee's have been achieved. This methodology provides an efficient catalytic method for the synthesis of both cis and trans chiral cyclic β-amino acid derivatives. Copyright
Synthesis of 4-methoxy-2,3,5-trimethylpyridine: a specific building block for compounds with gastric-acid inhibiting activity.
Mittelbach,Schmidt,Uray,Junek,Lamm,Ankner,Br?ndstr?m,Simonsson
, p. 524 - 529 (2007/10/02)
A new synthesis of 4-methoxy-2,3,5-trimethylpyridine (2), an important building block for the preparation of gastric-acid inhibiting compounds, is described. Condensation of ethyl 3-amino-2-methyl-2-butenoate (3) and diethyl 2-methylmalonate (4) gives 4-hydroxy-3,5,6-trimethyl-2(1H)-pyridone 5. Reaction of 5 with phosphoryl chloride affords 2,4-dichloro-3,5,6-trimethylpyridine (9a), which, upon hydrogenolysis with palladium on charcoal, gives 2,3,5-trimethylpyridine (10). However, selective hydrogenolysis in acidic solution yields 4-chloro-2-3-5-trimethylpyridine (11). Substitution of the chlorine in 11 with methoxide ion gives 4-methoxy-2,3,5-trimethylpyridine (2), which can be oxidized to the corresponding N-oxide (13). This constitutes a new and efficient route to compound 2 in an overall yield of 43%.
ENAMINE CHEMISTRY, PART XXI. N- AND/OR C-SUBSTITUTION (ALKYLATION, ACYLATION) OF ETHYL 3-AMINO-2-BUTENOATE. THE PREPARATION OF 2-SUBSTITUTED 4-METHYL-1,3-THIAZINE-6-THIONES
Shabana, R.,Rasmussen, J. B.,Lawesson, S.-O.
, p. 75 - 82 (2007/10/02)
Alkylation of ethyl 3-amino-2-butenoate, 1, with methyl iodide, ethyl iodide, and benzyl bromide gave both C- and N-alkylated products (contrary to earlier findings) the ratio of which was determined by GLC.Methylation of 1 was studied under different con
Steric and Conformational Effects in Nicotine Chemistry
Seeman, Jeffrey I.,Secor, Henry V.,Chavdarian, Charles G.,Sanders, Edward B.,Bassfield, Ronald L.,Whidby, Jerry F.
, p. 3040 - 3048 (2007/10/02)
The stereoselectivity of iodomethylation of nicotine and seven nicotine analogues having pyridine alkyl groups was determined by using 13C NMR.Alkylation at the pyridine (N) and at the pyrrolidine (N') nitrogens was observed.Two modes of N'-iodomethylation occur, cis and trans to the pyridine ring.N'-Iodomethylation occurs regioselectively cis to the pyridine ring for all compounds examined.The N/N' and N'cis/N'trans ratios for the nicotinoids were evaluated with regard to (1) the orientation of the N'-methyl group in the free base, (2) conformational properties of the pyridine ring with respect to the pyrrolidine ring, and (3) steric hindrance and buttressing effects on the pyridine nitrogen.The Curtin-Hammett principle and the Winstein-Holness equation are used to analyse reactions.