7166-64-5Relevant academic research and scientific papers
Benzylic Thio and Seleno Newman-Kwart Rearrangements
Eriksen, Kristina,Ulfkj?r, Anne,S?lling, Theis I.,Pittelkow, Michael
, p. 10786 - 10797 (2018/09/06)
The thermally induced OBn → SBn and OBn → SeBn migration reactions facilitate the rearrangement of O-benzyl thio- and selenocarbamates [BnOC(=X)NMe2] (X = S or Se) into their corresponding S-benzyl thio- and Se-benzyl selenocarbamates [BnXC(=O)NMe2] (X = S or Se). A series of substituted O-benzyl thio- and selenocarbamates were synthesized and rearranged in good yields of 33-88%. The reaction rates are higher for substrates with electron-donating groups in the 2 or 4 position of the aromatic ring, but the rearrangement also proceeds with electron-withdrawing substituents. The rearrangement follows first-order reaction kinetics and proceeds via a tight ion pair intermediate consisting of the benzylic carbocation and the thio- or selenocarbamate moiety. Computational studies support these findings.
Mercaptomethylation of aromatics
Nakamura, Tohru,Matsumoto, Mutsuyoshi
, p. 201 - 210 (2007/10/03)
Mercaptomethylarenes 2a - f were prepared in moderate yields by facile mercaptomethylation consisting of the metalation of the corresponding aromatics 1a - f with magnesium or butyllithium / magnesium bromide diethyl etherate, followed by the addition of O-propyl chlorothioformate, and the reduction with lithium aluminum hydride or sodium borohydride.
Novel Alkylation with Tetrathiotungstates and Tetrathiomolybdates: Facile Synthesis of Disulfides from Alkyl Halides
Dhar, Preeti,Chandrasekaran, Srinivasan
, p. 2998 - 3000 (2007/10/02)
A novel reaction of alkyl halides with piperidinium tetrathiotungstate or piperidinium tetrathiomolybdate (MS42-) has been found to afford disulfides in good to excellent isolated yields under very mild reaction conditions.
Imidazopyridazines. VI. Syntheses and Central Nervous System Activities of Some 6-(Alkoxy- and methylthio-phenoxy and methoxybenzylthio)-3-methoxy-2-phenyl(substituted phenyl and pyridinyl)imidazopyridazines
Barlin, Gordon B.,Davies, Les P.,Ireland, Stephen J.,Ngu, Maria M.L.
, p. 1735 - 1748 (2007/10/02)
Series of 6-(alkoxy- and methylthio-phenoxy)-2-phenyl(substituted phenyl and pyridinyl)imidazopyridazines and 3-methoxy-6-(methoxybenzylthio)-2-phenyl(substituted phenyl and pyridinyl)imidazopyridazines have been prepared and subsesquently tested for their ability to inhibit GABA-stimulated 3H-diazepam binding to rat brain plasma membranes.The 6-(alkoxy- and methylthio-phenoxy) and 6-(methoxybenzylthio) compounds were much more effective in the displacement studies than the parent 6-phenoxy or 6-benzylthio compounds respectively.3-Methoxy-6-(2'-methoxyphenoxy)-2-phenylimidazopyridazine (GBLD-167, IC50 70 nM) was 16 times more effective than its 3-methoxy-6-phenoxy analogue (GBLD-214, IC50 1120 nM) and the 3-methoxy-6-(2'-methoxybenzylthio)-2-phenyl compound (GBLD-163, IC50 9 nM) was two and a half times more active than its 6-benzylthio-3-methoxy analogue (GBLD-137, IC50 22nM).The most active member of the 6-phenoxy series was the 2-(4'-fluorophenyl)-3-methoxy-6-(2''-methoxyphenoxy) compound (GBLD-255, IC50 30nM) and, within the 6-benzylthio series, the 2-(4'-fluorophenyl, 3'-aminophenyl, and pyridin-3'-yl)-3-methoxy-6-(3''-methoxybenzylthio) compounds (GBLD-233, 301 and 296) all gave IC50 5nM.A Hansch-type analysis of the results for these two closely related series of compounds indicates that electron-donating substituents in 2-(para substituted phenyl) derivatives favour binding, but bulky substituents hinder this effect.
Intramolecular Alkylation of Phenols. Part 4. Base-catalysed Cyclisation of Phenolic Enones. Scope and Limitations
Murphy, William S.,Wattanasin, Sompong
, p. 1555 - 1566 (2007/10/02)
The phenolic enones (4), (5), (8), (9), and (13) cyclise readily under acidic conditions.However, neither these nor the thio-substituted phenols (11a), (13a), (14a), and (15a) closed under basic conditions.Involvement of unfavourable equilibria is disproved.Comparison is made with related successful cyclisations of the saturated ketone (38) and aldehyde (39).Preliminary results suggest that strict stereo-electronic requirements are necessary for enone ring closure and that these conditions are not met in base-catalysed 5-Endo- and 6-Endo-Trigonal ring closures of the phenols of general type (2; n=0 and n=1).
6,11-Dihydrodibenzo-[b.e.]-thiepin-11-one-3-thioacetates
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, (2008/06/13)
Novel thioesters of 6,11-dihydrodibenzo-[b.e.]-thiepin-11-one-3-acetic acid, (dl) 2-(6,11-dihydrodibenzo-[b.e.]-thiepin-11-one-3-yl)propionic acid and the individual (d) isomers of the latter, and processes for making the same.
