- Ag-Cu copromoted direct C2-H bond thiolation of azoles with Bunte salts as sulfur sources
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A direct C2-H thiolation of azoles with Bunte salts was achieved under the combined action of copper and silver salts. This protocol could furnish various substituted 2-thioazoles in moderate to good yields. This method has a broad substrate scope and shows good functional group tolerance.
- Du, Xiao,Hu, Yuntao,Wang, Rui,Wei, Yingsu,Xu, Hongyan,Zhang, Ying,Zhao, Huaiqing
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supporting information
p. 5899 - 5904
(2021/07/12)
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- Novel 3-methyl-2-alkylthio benzothiazolyl-based ionic liquids: Synthesis, characterization, and antibiotic activity
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Three series of novel 3-methyl-2-alkylthio benzothiazolyl ionic liquids (ILs) were synthesized for the first time. After structural identification, their melting point, solubility, and thermostability together with antibiotic activity were determined successively. As a result, 3-methyl-2-alkylthio benzothiazolyl p-toluene sulfonate was found to have the highest antibacterial activity among the three series of ILs. Meanwhile, it has a good solubility in water as well. On the basis of comprehensive comparison with similar compounds, the effect of cations and anions of these benzothiazolium ILs on typical physical properties together with antibiotic performance was explored and discussed, which is very beneficial to take the greatest advantage of their structural designability for various purposes. Furthermore, the experiment data preliminarily discovered the relationships of the structure-properties/activities of the above three kinds ILs to a certain extent, which can provide useful references for future research and for the potential application of these new ILs as surfactant antiseptics or agricultural chemicals.
- Zhang, Teng He,He, Hao Xi,Du, Jun Liang,He, Zhi Jian,Yao, Shun
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- A novel synthesis of 2-alkylthiobenzothiazoles and 2-alkylthiobenzoxazoles
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3H-Benzothiazole-2-thione and 3H-benzoxazole-2-thione were selectively S-alkylated by use of O-alkylisoureas as the alkylating reagents. The reactions could be performed under mild reaction conditions in short reaction times, and high yields were obtained using O-primary-alkylisoureas, whereas low yields were obtained with sec-and tert-alkylisoureas.
- Yu, Yanfei,Li, Zhengning,Jiang, Lan
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experimental part
p. 632 - 640
(2012/06/01)
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- Alkylation of SH-heterocycles with diethyl phosphite using tetrachloroethylene as an efficient solvent
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Treatment of mercapto-heterocyclic compounds with diethyl phosphite in the presence of 4-dimethylaminopyridine (DMAP) in tetrachloroethylene has given the S-ethylated product in good yields and high chemoselectivity. This procedure is compatible with a wide range of SH-compounds such as 1,3,4-oxadiazole-2-thiol, 1,3,4-thiadiazole-2-thiol, benzo[d]thiazole-2-thiol, and substituted benzenethiol. Copyright
- Quan, Zheng-Jun,Ren, Rong-Guo,Da, Yu-Xia,Zhang, Zhang,Wang, Xi-Cun
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experimental part
p. 653 - 658
(2011/12/15)
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- Thermal reactions of β-hydroxysulfides bearing benzothiazole: Sulfenic acid trapping via a spiro intermediate
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Benzothiazolyl 2-hydroxyethyl sulfoxide (1a) was found to afford bis[2-(2-oxobenzotiazolyl)-ethyl] disulfide (2a) in the presence of DBU at rt. 2a was formed by the condensation of corresponding sulfenic acid intermediate. Thermolyses of 1a in the presence of ethyl propiolate at 60-140C were carried out to succeed to trap sulfenic acid 6a as an intermediate. Trapping of 2-benzothiazolyloxyenthanesulfenic acid (6a) revealed that the thermal reaction proceeded via a five-membered spiro intermediate 5a. Copyright Taylor & Francis Group.
- Yamada, Nobuhiko,Koyasu, Takanori,Sonami, Mayumi,Aoi, Michiko,Tashiro, Shintaro,Sheikh, Md. Chanmiya,Ishida, Yusuke,Kawashima, Wataru,Yoshimura, Toshiaki,Morita, Hiroyuki
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experimental part
p. 1142 - 1153
(2010/08/21)
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- An easy and fast ultrasonic selective S-alkylation of hetaryl thiols at room temperature
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A series of 2-alkylthio derivatives of hetaryl thiols were synthesized by selective S-alkylation with alkyl halides (bromides and iodides) with ultrasonic irradiation at room temperature. The reaction was found to be generally applicable to hetaryl thiol derivatives with different substituents in the aromatic nucleus and various alkyl halides. The reaction gives high to excellent yields of products with high purity.
- Deligeorgiev, Todor,Kaloyanova, Stefka,Lesev, Nedyalko,Vaquero, Juan J.
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experimental part
p. 783 - 788
(2011/10/09)
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- Fly-ash-supported synthesis of 2-mercaptobenzothiazole derivatives under microwave irradiation
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Microwave-assisted, solvent-free alkylation and acylation of 2-mercaptobenzothiazole has been attempted using silica gel, alumina, and a new solid support, fly ash. Fly ash, a waste generated at thermal power stations, could be used as solid support just as efficiently as commercial supports. The additional features of methodology include a much faster reaction, easy workup, higher yields, higher purity of the products, and an ecofriendly approach. Copyright Taylor & Francis Group, LLC.
- Narkhede, Hemant P.,More, Uttam B.,Dalal, Dipak S.,Pawar, Nilesh S.,More, Dhananjay H.,Mahulikar, Pramod P.
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p. 575 - 579
(2007/10/03)
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- 1,3,5-SUBSTITUTED PHENYL DERIVATIVE COMPOUNDS USEFUL AS BETA-SECRETASE INHIBITORS FOR THE TREATMENT OF ALZHEIMER'S DISEASE
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The present invention is directed to 1,3,5-phenyl substituted derivative compounds which are inhibitors of the beta-secretase enzyme and that are useful in the treatment of diseases in which the beta-secretase enzyme is involved, such as Alzheimer's disease. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the treatment of such diseases in which the beta-secretase enzyme is involved.
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Page/Page column 91
(2010/02/14)
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- Preparation of monofluoroalkenes
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There is described a process for the preparation of compounds of formula I in whichR is hydrogen, optionally substituted alkyl, optionally substituted alkenyl optionally substituted cycloalkyl, optionally substituted phenyl or optionally substituted heterocyclyl, andR1 and R2 are hydrogen, an organic radical or together with the ring to which they are attached, form an optionally substituted ring, which may contain one or more hetero atoms, which comprises reacting a compound of formula II with a compound of formula III in which the ring Q is an optionally substituted heteroaromatic ring, which optionally comprises one or more further hetero atoms and to which is optionally fused an optionally substituted ring.
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- Synthesis of alkylthio- and arylthioheteroarenes by regioselective grignard reaction of thiocyanatoheteroarenes
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Treatment of thiocyanatoheteroarenes (1) with Grignard reagents (2) afforded alkylthio- or arylthioheteroarenes (3-6) in good yields. Grignard reagents regioselectively attacked the sulfur atom of the thiocyanato group owing to the metal-chelating effect of this group in combination with the hetero ring-nitrogen. 2-Thiocyanatopyridine (1a), 2-thiocyanatopyrimidine (1b), 2-thiocyanatobenzothiazole (1c), and 4-thiocyanatoquinazoline (1d) were converted into a variety of sulfides. Sulfides consisting of two heteroarenes linked by a sulfur atom were readily obtained by this method.
- Nagasaki, Izuru,Matsumoto, Miyuki,Yamashita, Masanori,Miyashita, Akira
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p. 1015 - 1024
(2007/10/03)
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- Contra-thermodynamic trans-esteripication of carbamates by counter-attack strategy: A viable non-phosgene, non-mic route to carbamate pesticides
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Treatment of methyl N-methylcarbaaate (1, R= Me) with phosphorus oxychloride and 1-naphthol results in the formation of the transesterified product, 1-naphthyl N-methylcarbamate (2, Ar=1-naphthy 1) in good yield. Similarly, ethyl N-methylthiocarbamate (5) is converted to 1-naphthyl N-methylcarbamate (2, Ar= 1-naphthyl) on treatment with phosphorus oxychloride and 1-naphthol. The mechanism of these interesting and industrially important transformations is discussed.
- Kulkarni,Naik,Tandel,Rajappa
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p. 1249 - 1256
(2007/10/02)
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- REACTION OF (2-BENZOTHIAZOLYL)-SULFENAMIDES WITH P-CONTAINING REAGENTS
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The title reaction was investigated to find that only substitution reaction on amino group occured when (2-benzothiazoly)sulfenamides 1 reacted with P(NR2)3, whereas the treatment of 1 with (RO)P(NR2)2 gave derivatives of phosphorodiamidothioic acid together with 2-alkylthiobenzothiazole and its isomer in addition to substitution products, and no substitution products obtained when N-substituted analogues of 1 were treated similarly.
- Zhang, Jing-Lin,Ma, Xiao-Bo
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- An Unusual S- and N-Alkylation of Mercapto Substituted Heterocycles with O,O-Dialkyl Chlorophosphate/Thiophosphate
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The reaction of different mercapto substituted heterocycles with O,O-dialkyl chlorophosphate or thiophosphates, gave the corresponding S- and N- alkylated derivatives instead of the expected phosphorylated products.
- Rani, B. Radha,Bhalerao, U.T.,Rahman, M.F.
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p. 3045 - 3052
(2007/10/02)
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- Reactions of (Benzothiazol-2-ylthio)(trimethylsilyl)methane. A General Method for α-Mercaptoalkylation by Alkylation and Alkylative Desilylation
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Readily available (benzothiazol-2-ylthio)(trimethylsilyl)methane (2a) provides a convenient synthon for HSCH2- and enables the general conversions RR'CO -> RR'C(OH)CH(SH)R'' and RBr -> RCH(SH)SiMe3.The lithium derivative of 2a reacts with aldehydes and ketones to give Peterson olefination products which are protected vinyl mercaptans converted into vinyl mercaptans by reaction with methyllithium.This overall conversion is RR'CO -> RR'C:CHSH.
- Katritzky, Alan R.,Kuzmierkiewicz, Wojciech,Aurrecoechea, Jose M.
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p. 844 - 849
(2007/10/02)
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- Carbanions Derived from 2-Alkylthiobenzothiazoles. A Novel α-Lithiomethyl Mercaptan Synthon for Mercaptomethylation.
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2-Methylthiobenzothiazole readily gives a methyl group lithio derivative which reacts cleanly with electrophiles.The products are conveniently converted into the corresponding thiols by BuLi at -78 deg C, and this sequence thus provides a convenient two-step mercaptomethylation procedure for alkyl halides, aldehydes, and ketones.
- Katritzky, Alan R.,Aurrecoechea, Jose M.,Vazques de Miguel, Luis M.
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p. 769 - 774
(2007/10/02)
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- A NEW METHOD OF N-ACETALIZATION AND S- OR N-ETHYLATION BY MEANS OF ORTHOFORMIC ESTER
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A new method is proposed for the synthesis of amidoacetals by acetalization of the imino group with orthoformic ester.The thermal instability of the obtained amidoacetals in the presence of groups having a clearly defined negative inductive effect leads to the formation of S- or N-ethylated products.
- Rutavichyus, A. I.,Iokubaitite, S. P.
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p. 2371 - 2375
(2007/10/02)
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- An ESR Study of the Cation Radicals of Azodibenzothiazolyls
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Methyl and ethyl derivatives of thiobenzothiazole and their quaternary salts were prepared by the sealed glass tube method.Azinodibenzothiazoles were oxidized by lead(IV) acetate, giving cation radical salts with the boron tetrafluoride anion moiety.The well-resolved esr spectra observed were analyzed by comparing the data with those of a deuteriomethylated radical and with those from the MO calculations.Spin density distribution was consistently determined by computer simulation, including almost the same unpaired electron distribution on the four nitrogen atoms.
- Okada, Keiichi,Yamauchi, Jun,Deguchi, Yasuo
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p. 723 - 727
(2007/10/02)
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- CARBON-CARBON BOND FORMATION VIA PHOSPHINE-INITIATED CLEAVAGE OF β-OXOSULFIDES
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2-(Phenacylthio)benzothiazole (1) reacted with aldehyde or ketone in the presence of tri-n-butylphosphine at 80 deg C to give α,β-enone and 2-mercaptobenzothiazole in good yield.The reaction scheme for this new type of enolate ion formation via C-S bond cleavage is also described.
- Ueno, Yoshio,Yadav, L. D. S.,Okawara, Makoto
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p. 831 - 834
(2007/10/02)
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- REACTION OF SULFENAMIDES WITH DI-ALKYL AND TRIALKYL PHOSPHITES. AN EFFICIENT SYNTHESIS OF PHOSPHORAMIDATES BY UNUSUAL SUBSTITUTION AT S-N BOND IN (2-BENZOTHIAZOLYL)SULFENAMIDES
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Regioselective attack of the trivalent phosphorus atom of dialkyl and trialkyl phosphites on either nitrogen or sulfur atom of sulfenamides has been found.The reaction of phenylsulfenamides with dialkyl phosphites yielded phosphorothiolates, whereas the treatment of (2-benzothiazolyl)sulfenamides with dialkyl and trialkyl phosphites gave phosphoramidates in excellent yields.
- Torii, Sigeru,Sayo, Noboru,Tanaka, Hideo
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p. 695 - 698
(2007/10/02)
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