20996-62-7Relevant articles and documents
METHOD FOR PRODUCING PYRIDINE COMPOUND
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Paragraph 0260, (2020/01/24)
The present invention provides a method for producing a compound represented by formula (4), which is useful as, for example, an agrochemical or an intermediate for agrochemical production, the method including the step of reacting a compound represented by formula (2) with an organic oxidant. [In the formulae, Q represents a pyridyl group, etc.; R1 represents a C1-6 alkyl group optionally having one or more halogen atoms; R2 represents, for example, a C1-6 alkyl group optionally having one or more halogen atoms; R3, R4, and R5 each represent a hydrogen atom, etc.; and n is 0, etc.]
Humicola lanuginosa lipase-catalyzed enantioselective resolution of β-hydroxy sulfides: Versatile synthons for enantiopure β-hydroxy sulfoxides
Singh, Satwinder,Kumar, Subodh,Chimni, Swapandeep Singh
, p. 2457 - 2462 (2007/10/03)
Humicola lanuginosa lipase-catalyzed acylation of β-hydroxy sulfides provides both the (R)- and (S)-enantiomers in high enantiomeric purity. In two cases the resolved hydroxy sulfides were oxidized to give β-hydroxy sulfoxides in >99% e.e. The effect of substituents on enantioselectivity is discussed.
Highly chemoselective α-diazo carbonyl insertion reactions into N-H and S-H bonds catalysed by [RuCl(η5-C5H5)(PPh3)2]
Del Zotto, Alessandro,Baratta, Walter,Rigo, Pierluigi
, p. 3079 - 3082 (2007/10/03)
Complex [RuCl(η5-C5H5)(PPh3)2], in chloroform at 60 deg C, catalyses the chemoselective insertion of α-diazo carbonyl compounds into N-H and S-H bonds to afford α-keto-amines and α-keto-thioethers.
Generation and synthetic application of metallated methyl isopropenyl ether, a substitute for acetone enolate
Taherirastgar, Foroogh,Brandsma, Lambert
, p. 45 - 48 (2007/10/03)
Methyl isopropenyl ether (1) has been metallated at low temperature with a 1:1 molar mixture of n-BuLi/t-BuOK in THFhexane, and subsequently functionalized with a variety of electrophilic reagents. At temperatures higher than -30°C, the metallated methyl isopropenyl ether (2) decomposes with formation of allene. When the suspension of 2 is allowed to warm up to room temperature in the presence of an additional equivalent of n-BuLi, the intermediary aliene is converted into 1-propynyllithium (2c), which reacts with propyl thiocyanate to give 1-propylthio-1-propyne (4). Some of the functionalization products were subjected to acidic hydrolysis affording the expected methyl ketones. VCH Vcrlagsgescllschaft mbH.
Sulfur substituted small-ring heterocycles
Zwanenburg,Philipse,Verstappen,Gieling
, p. 453 - 454 (2007/10/03)
The synthesis of epoxy sulfines and sulfonyl azirines is described.
Inter- and Intramolecular Hetero-Diels-Alder Reactions, 37. Syntheses of the 3-Amino Sugar Glycosides rac-4-Deoxydaunosaminide, rac-4-Deoxyristosaminide, and rac-Acosaminide
Tietze, Lutz F.,Hartfiel, Uwe,Huebsch, Thomas,Voss, Edgar,Bogdanowicz-Szwed, Krystyna,Wichmann, Juergen
, p. 275 - 281 (2007/10/02)
The hetero-Diels-Alder reaction of the phenylthio-activated N-monoacyl- and N,N-diacyl-enamino ketones 8a-c containing a methyl group at position 2 of the oxadiene with the electron-rich dienophiles 9a-c yields the exo/endo adducts 10a-d and 11a-d in 82-95percent yield with the endo adducts as the main products.The enamino ketone 8d with a S-ethyl group at C-3 does not react.Hydrogenation of 11a with Raney nickel in THF leads to the desulfurized dihydropyran 12, whereas in MeOH gives stereoselectively the perhydrophthalimido derivative 13, which, after deprotection, yieldsthe β-methyl glycoside 14 of rac-4-deoxydaunosamine.Under similar conditions 10c is converted into the β-ethyl glycoside 15 of rac-N-benzoyl-4-deoxyristosamine.Stereoselective hydroboration of 12 affords 17 and subsequent cleavage of the protecting group leads to the β-methyl glycoside 18 or rac-acosamine.
REACTION OF Α-CHLORO KETONES WITH THIOLS
Mursakulov, I. G.,Ramazanov, E. A.,Kerimov, F. F.,Abbasov, I. M.,Zefirov, N. S.
, p. 1416 - 1425 (2007/10/02)
The reaction of α-chloro ketones with ethane-, propane-, and butanethiols leads to the corresponding (alkylthio)alkenes.Noncyclic chloro ketones give a mixture of the cis and trans isomers of di(alkylthio)alkenes, while the reaction of α-chloropinacoline leads only to the cis isomers of the 1,2-di(alkylthio)-3,3-dimethyl-1-butene.The mechanism of the reaction of α-chloro ketones with thiols includes nucleophilic substitution of the chlorine with the formation of alkylthio ketones.The addition of a further molecule leads to the corresponding intermediate alkylthio a cohols, which are easily dehydrated to the final products under the acidic conditions.
Nonsteroidal antiandrogens. Synthesis and structure-activity relationship of 3-substituted derivatives of 2-hydroxypropionanilides
Tucker,Crook,Chesterson
, p. 954 - 959 (2007/10/02)
A series of 3-(substituted thio)-2-hydroxypropionanilides and some corresponding sulfones and sulfoxides of general structure 7, in which R' is methyl or trifluoromethyl, were prepared and tested for antiandrogen activity. Members of the trifluoromethyl series (7,R' = CF3) generally exhibited partial androgen agonist activity whereas the members of the methyl series (7,R' = CH3) were pure antagonists. Lead optimization in the methyl series has led to the discovery of novel, potent antiandrogens, which are peripherally selective. One of these, (RS)-4'-cyano-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methyl-3'-(trifd luoromethyl)propionanilide, 40 (ICI 176334), is being developed currently for the treatment of androgen-responsive benign and malignant disease.
Structure-Stability Relationships in Vinyl Sulfides. II. Stabilization Energies due to Alkyl and Alkylthio Groups Attached to the β Carbon of Vinyl Sulfides and Vinyl Ethers
Kimmelma, Reijo,Taskinen, Esko
, p. 271 - 277 (2007/10/02)
On the basis of equilibration studies, it is concluded that a methyl group stabilizes the double bond of a vinyl sulfide by about 8.5 kJ mol-1 when the group is in the trans position on the β carbon of an α,β-dimethyl substituted vinyl sulfide, and by about 9.5 kJ*mol-1 in the corresponding position of a trimethyl substituted vinyl sulfide.An ethylthio group in the trans position on the β carbon stabilizes the double bond by about 8 kJ mol-1 or 5 kJ mol-1 in vinyl ethers with one (at the α carbon) or two methyl groups, respectively.The corresponding stabilization energy when the ethylthio group is in the trans position in corresponding vinyl sulfides are about 16 kJ mol-1 and 5 kJ mol-1.The result that the stabilization is smaller when two methyl groups are attached to the double bond is explained on the basis that the ethylthio group in these molecules has to adopt an energetically unfavourable gauche conformation.
