- Facile synthesis of 2-(substitutedbenzylsulfanyl)-benzothiazoles and their antimicrobial activity screening
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A simple and convenient procedure for the preparation of 2-(substitutedbenzylsulfanyl)benzothiazoles by the reaction of 2-mercaptobenzothiazole and benzyl bromides in acetone/K2CO 3 has been reported and the compounds have been scree
- Kumar, Ramanatham Vinod,Kumar, Kotha V. S. R. Seshu,Gopal, Kotarkonda Raja
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Read Online
- Conformational Analysis of Acyclic α-Fluoro Sulfur Motifs
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Bioactive small molecules containing α-fluoro sulfur motifs [RS(O)nCH2F] are appearing with increasing frequency in the pharmaceutical and agrochemical sectors. Prominent examples include the anti-asthma drug Flovent and t
- Erdeljac, Nathalie,Mück-Lichtenfeld, Christian,Daniliuc, Constantin G.,Gilmour, Ryan
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Read Online
- Preparation of alkyl aryl sulfides from alcohols and 2- sulfanylbenzothiazole by a new type of oxidation-reduction condensation using aryl diphenylphosphinite and benzoquinone derivatives
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A method for the preparation of alkyl aryl sulfides from alcohols and 2-sulfanylbenzothiazole by a new type of oxidation-reduction condensation using phenyl diphenylphosphinite and 2.6-dimethoxy-1,4-benzoquinone is described. In this reaction, the chiral alcohols are converted into the corresponding chiral sulfides with almost complete inversion of configurations under mild and neutral conditions. Copyright
- Kuroda, Kiichi,Heyashi, Yujiro,Mukaiyama, Teruaki
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Read Online
- Discriminating non-ylidic carbon-sulfur bond cleavages of sulfonium ylides for alkylation and arylation reactions
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A sulfonium ylide participated alkylation and arylation under transition-metal free conditions is described. The disparate reaction pattern allowed the separate activation of non-ylidic S-alkyl and S-aryl bond. Under acidic conditions, sulfonium ylides serve as alkyl cation precursors which facilitate the alkylations. While under alkaline conditions, cleavage of non-ylidic S-aryl bond produces O-arylated compounds efficiently. The robustness of the protocols were established by the excellent compatibility of wide variety of substrates including carbohydrates.
- Fang, Jing,Li, Ting,Ma, Xiang,Sun, Jiuchang,Cai, Lei,Chen, Qi,Liao, Zhiwen,Meng, Lingkui,Zeng, Jing,Wan, Qian
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p. 288 - 292
(2021/07/25)
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- 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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- Unusual Deoxidative Coupling Reaction of β-Sulfinyl Esters with Benzylic Trimethylammonium Salts
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A KOH-promoted unusual deoxidative coupling reaction of β-sulfinyl esters with benzylic trimethylammonium salts to produce thioethers is discovered for the first time. If quaternary ammonium salts synthesized from enantiomerically enriched amines are adopted, highly enantiomerically enriched benzyl thioethers (>95-99% ee) with configurations opposite to those of the enantiomerically enriched amines are obtained.
- Chen, Feng,Feng, Hang,He, Ze,Zeng, Qingle,Zhang, Qiaoling
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p. 7806 - 7812
(2021/06/25)
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- One-Pot Substitution of Aliphatic Alcohols Mediated by Sulfuryl Fluoride
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The Mitsunobu reaction is a powerful transformation for the one-pot activation and substitution of aliphatic alcohols. Significant efforts have focused on modifying the classic conditions to overcome problems associated with purification from phosphine-based byproducts. Herein, we report a phosphine free method for alcohol activation and substitution that is mediated by sulfuryl fluoride. This new method is effective for a wide range of primary alcohols using phthalimide, di-tert-butyl-iminodicarboxylate, and aromatic thiol nucleophiles in 74 % average yield. Activated carbon nucleophiles and a deactivated phenol were also effective for this reaction in good yields. Secondary alcohols were also successful substrates using aryl thiols, affording the corresponding sulfides in 56 % average yield with enantiomeric ratios up to 99:1. This new protocol has a distinct synthetic advantage over many existing phosphine-based methods as the byproducts are readily separable. This feature was exploited in several examples that did not require chromatography for purification. Furthermore, the mild reaction conditions enabled further in situ derivatization for the one-pot conversion of alcohols to amines or sulfones. This method also provides a boarder nucleophile scope compared to existing phosphine-free methods.
- Dubois, Rudy,Epifanov, Maxim,Hodgson, Jack W.,Mo, Jia Yi,Sammis, Glenn M.
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supporting information
p. 4958 - 4962
(2020/04/22)
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- Three-Component Synthesis of 2-Substituted Thiobenzoazoles Using Tetramethyl Thiuram Monosulfide (TMTM) as Thiocarbonyl Surrogate
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A metal-free synthesis of 2-benzyl/allyl-substituted thiobenzoazoles was developed starting from tetramethyl thiuram monosulfide (TMTM) which served as thiocarbonyl surrogate. By using 2-aminophenols (or 2-aminothiophenols, or 1,2-phenylenediamines) and TMTM as starting materials, 2-mercaptobenzoazoles could be synthesized efficiently. The subsequent C–S bond formation with benzyl/allyl halides gave the final products (2-benzyl/allyl-substituted thiobenzoazoles) with good to excellent yields. The metal-free conditions, inexpensive and easily available starting materials, and broad substrate scope are the advantageous features of this protocol.
- Wang, Xi,Wu, Chun-Yan,Li, Yue-Sheng,Dong, Zhi-Bing
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p. 6770 - 6775
(2020/11/23)
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- Transition metal-free coupling reactions of benzylic trimethylammonium salts with di(hetero)aryl disulfides and diselenides
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A new protocol was developed to synthesize (enantioenriched) thioethers and selenoethers from (chiral) benzylic trimethylammonium salts and di(hetero)aryl disulfides or diselenides. These syntheses were promoted by the presence of weak base and did not require the use of any transition metal, and resulted in the target products with good to excellent yields (72-94%). Using quaternary ammonium salts synthesized from enantiomerically enriched amines led to highly enantiopure benzylic thioethers and selenoethers (94-99% ee) with configurations reversed from those of their enantioenriched quaternary ammonium salts. This journal is
- Li, Fuhai,Wang, Dan,Chen, Hongyi,He, Ze,Zhou, Lihong,Zeng, Qingle
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p. 13029 - 13032
(2020/11/07)
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- Selective C-H chalcogenation of thiazoles: Via thiazol-2-yl-phosphonium salts
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Thiazoles and benzothiazoles undergo regioselective C2-H chalcogenation via the sequence of thiazole C2-functionalization with phosphines to produce phosphonium salts which in turn react with S- and Se-centered nucleophiles to give products of C2-H chalco
- Zi, You,Wagner, Konrad,Sch?mberg, Fritz,Vilotijevic, Ivan
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p. 5183 - 5191
(2020/07/23)
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- One-pot preparation of Julia-Kocienski sulfides and sulfones from alcohols
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A method for one-pot preparation of Julia-Kocienski sulfides and sulfones from alcohols and thiols is reported. A variety of primary alcohols were converted to the corresponding mesylates by methansulfonyl chloride and triethylamine in THF. After the reaction is complete, thiol (1 or 10) and either NaH or t-BuOK were added. The Julia-Kocienski sulfides 3, 9 and 11 were prepared by one-pot two steps procedure from alcohols in 76–96% yields (16 examples). Furthermore, after the sulfide formation, the reaction mixture was neutralized by p-toluenesulfonic acid and treated with H2O2 and ammonium molybdate in EtOH to give the Julia-Kocienski sulfones 4 in good yields except for trans-2-hexen-1-ol.
- Ando, Kaori,Hattori, Junichiro
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- Facile synthesis of a series of non-symmetric thioethers including a benzothiazole moiety and their use as effcient in vitro anti-trypanosoma cruzi agents
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A series of 2-benzylsulfanyl benzothiazole (BTA) derivatives were synthesized and fully characterized and in vitro tested against two strains of T. cruzi (NINOA and INC-5), exhibiting good activities at low concentrations.
- Avila-Sorrosa, Alcives,Tapia-Alvarado, Jazz D.,Nogueda-Torres, Benjamín,Chacón-Vargas, Karla Fabiola,Díaz-Cedillo, Francisco,Vargas-Díaz, María Elena,Morales-Morales, David
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- One-pot sequential synthesis and antifungal activity of 2-(benzylsulfonyl)benzothiazole derivatives
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New antifungal agrochemicals, derived from 2-(benzylsulfonyl)benzothiazole were synthesized by an environmentally friendly method, using water as reaction medium. These compounds were prepared by a one-pot, two-step synthesis, starting from 2-mercaptobenzothiazole and benzyl halides. The potential fungicides were tested against a panel of phytopathogenic fungi, with many of them showing a significant improvement compared to the non-oxidized analogues and the commercial antifungal Captan. The new derivatives 2-((2-chlorobenzyl)sulfonyl)benzo[d]thiazole (4f) and 2-((4-methylbenzyl)sulfonyl)benzo[d]thiazole (4k) presented remarkable properties, being able to inhibit the growth of two resistant moulds (Aspergillus fumigatus and Aspergillus ustus). Both 4f and 4k could be classified as broad-spectrum fungicides, emerging as possible candidates for the control of these moulds, which have negative impact in food production.
- Ballari, María Sol,Herrera Cano, Natividad,Wunderlin, Daniel A.,Feresin, Gabriela E.,Santiago, Ana N.
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p. 29405 - 29413
(2019/09/30)
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- Nanolayered cobalt-molybdenum sulphides (Co-Mo-S) catalyse borrowing hydrogen C-S bond formation reactions of thiols or H2S with alcohols
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Nanolayered cobalt-molybdenum sulphide (Co-Mo-S) materials have been established as excellent catalysts for C-S bond construction. These catalysts allow for the preparation of a broad range of thioethers in good to excellent yields from structurally diverse thiols and readily available primary as well as secondary alcohols. Chemoselectivity in the presence of sensitive groups such as double bonds, nitriles, carboxylic esters and halogens has been demonstrated. It is also shown that the reaction takes place through a hydrogen-autotransfer (borrowing hydrogen) mechanism that involves Co-Mo-S-mediated dehydrogenation and hydrogenation reactions. A novel catalytic protocol based on the thioetherification of alcohols with hydrogen sulphide (H2S) to furnish symmetrical thioethers has also been developed using these earth-abundant metal-based sulphide catalysts.
- Corma, Avelino,Sorribes, Iván
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p. 3130 - 3142
(2019/03/13)
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- Promoting Effect of Crystal Water Leading to Catalyst-Free Synthesis of Heteroaryl Thioether from Heteroaryl Chloride, Sodium Thiosulfate Pentahydrate, and Alcohol
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It is observed the crystal water in sodium thiosulfate pentahydrate (Na2S2O3·5H2O) can promote its multicomponent reaction with heteroaryl chlorides and alcohols, providing a facile, green, and specific synthesis of unsymmetrical heteroaryl thioethers via one-step formation of two C-S bonds under catalyst-, additive-, and solvent-free conditions. Mechanistic studies suggest that the crystal water in Na2S2O3·5H2O is crucial in generating the key thiol intermediates and byproduct NaHSO4, which then catalyzes the dehydrative substitution of alcohols with thiols to afford thioethers.
- Ma, Xiantao,Yu, Jing,Yan, Ran,Yan, Mengli,Xu, Qing
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p. 11294 - 11300
(2019/09/12)
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- One-Pot Synthesis of 2-Benzyl/2-Allyl-Substituted Thiobenzoazoles Using Transition-Metal-Free Conditions in Water
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A transition-metal-free protocol for the one-pot synthesis of 2-benzyl/2-allyl-substituted thiobenzoazoles in water was developed. The cyclization of 2-aminothiophenols, 2-aminophenols, and 1,2-phenylenediamines with tetramethylthiuram disulfide (TMTD) gave mercapto benzoheterocycles, and the subsequent C-S coupling with benzyl or allyl halides furnished the desired products in good to excellent yields. This method features transition-metal-free conditions with water as a solvent, an easy performance, mild reaction conditions, a wide substrate scope, and good to excellent yields, thus paving an efficient and useful way to establish a library of potentially active drug molecules.
- Zhang, Shi-Bo,Liu, Xing,Gao, Ming-Yuan,Dong, Zhi-Bing
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p. 14933 - 14941
(2019/01/04)
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- Green Synthesis of Potential Antifungal Agents: 2-Benzyl Substituted Thiobenzoazoles
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A series of benzyl-substituted thiobenzoazoles were synthesized by an environmentally friendly approach, to search for new antifungal agrochemicals. Compounds were prepared starting from 2-mercaptobenzoazoles, using KOH, benzyl halides, and water, resulting in a simple and ecological method. New antifungals were tested against a group of phytopathogenic fungi. Two compounds showed an interesting activity against Botrytis cinerea, Fusarium oxysporum, and Aspergillus spp.: 2-((4-(trifluoromethyl)benzyl)thio)benzo[d]thiazole, 3ac, and 2-((4-methylbenzyl)thio)benzo[d]thiazole, 3al. Thus, 3ac and 3al can be considered as broad spectrum antifungal agents. Furthermore, two new compounds, 2-((4-iodobenzyl)thio)benzo[d]thiazole, 3aj, and 2-(benzylthio)benzo[d]oxazole, 3ba, showed better inhibitory effect against Botrytis cinerea and Fusarium oxysporum when compared to the commercial fungicide Captan. Thus, 3aj and 3ba can be considered reduced-spectrum antifungals.
- Ballari, María Sol,Herrera Cano, Natividad,Lopez, Abel Gerardo,Wunderlin, Daniel Alberto,Feresín, Gabriela Egly,Santiago, Ana Noemí
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p. 10325 - 10331
(2017/12/06)
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- S-Substituted-2-mercaptobenzthiazolium-based chiral ionic liquids: efficient organocatalysts for enantioselective sodium borohydride reductions of prochiral ketones
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Novel chiral ionic liquids having chirality in their cationic part have been synthesized for evaluation of their catalytic potential as organocatalysts in sodium borohydride reduction of prochiral ketones to yield optically active secondary alcohols. The chiral ionic liquids have been synthesized from the reaction of (?)-menthol or (?)-borneol, chloroacetic acid and S-methyl/benzyl-2-mercaptobenzthiazole. The synthesized chiral ionic liquids have been characterized by 1H, 13C NMR and Mass spectrometry. Moderate to excellent enantiomeric excess (ee?>?99%) has been obtained in asymmetric sodium borohydride reduction of prochiral ketones using these salts as chiral catalysts.
- Singh, Avtar,Chopra, Harish Kumar
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p. 414 - 418
(2017/03/23)
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- Zinc oxide catalyzed solvent-free mechanochemical route for C-S bond construction: A sustainable process
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A zinc oxide catalyzed solvent-free mechanochemical process has been developed for the rapid construction of C-S bonds by using a nucleophilic substitution reaction (SN2 mechanism) that involves a variety of thiols and phenacyl/ benzyl/alkyl bromides. Notable advantages of this method in-clude its broad substrate scope, clean reaction profile, safety, scalability, high product yields at ambient conditions, and the recyclability of the catalyst. Furthermore, the prepared compounds are valuable building blocks for the synthesis of various biologically active molecules.
- Md. Khaja Mohinuddin,Gangi Reddy
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p. 1207 - 1214
(2017/12/07)
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- Efficient Generation of C–S Bonds via a By-Product-Promoted Selective Coupling of Alcohols, Organic Halides, and Thiourea
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A metal- and base-free three-component coupling of alcohols, heteroaryl halides, and thiourea has been developed for direct and selective synthesis of heteroaryl thioethers. This method can be easily scaled up to the gram scale and extended to dialkyl thioethers, heteroaryl selenides, benzothiazoles, and some antimycobacterially-active thioethers. Mechanistic studies revealed that a by-product-promoted in situ C–O activation of alcohols to more reactive alkyl halides and slow release of the thiol and alkyl halide intermediates are the key to the high selectivity and success of the reaction. (Figure presented.).
- Ma, Xiantao,Yu, Lei,Su, Chenliang,Yang, Yaqi,Li, Huan,Xu, Qing
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supporting information
p. 1649 - 1655
(2017/05/29)
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- Enantioselective Sulfoxidation Catalyzed by a Bisguanidinium Diphosphatobisperoxotungstate Ion Pair
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The first enantioselective tungstate-catalyzed oxidation reaction is presented. High enantioselectivities were achieved for a variety of drug-like phenyl and heterocyclic sulfides under mild conditions with H2O2, a cheap and environmentally friendly oxidant. Synthetic utility was demonstrated through the preparation of (S)-Lansoprazole, a commercial proton-pump inhibitor. The active ion-pair catalyst was identified to be bisguanidinium diphosphatobisperoxotungstate using Raman spectroscopy and computational studies.
- Ye, Xinyi,Moeljadi, Adhitya Mangala Putra,Chin, Kek Foo,Hirao, Hajime,Zong, Lili,Tan, Choon-Hong
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supporting information
p. 7101 - 7105
(2016/07/06)
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- A comparative study of Cu(II)-assisted vs Cu(II)-free chalcogenation on benzyl and 2°/3°-cycloalkyl moieties
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A relative synthetic strategy toward intermolecular oxidative C -Chalcogen bond formation of alkanes has been illustrated using both Cu(II) assisted vs Cu(II) free conditions. This led to construction of a comparative study of hydrocarbon benzylic and 2°/ 3°-cycloalkyl moieties bond sulfenylation and selenation protocol by the chalcogen sources, particularly sulfur and selenium, respectively. In addition, this protocol disclosed the auspicious formation of sp3 C-S coupling products over leading the sp3 C-N coupling products by using 2-mercaptobenzothiazole (MBT) substrates.
- Sahoo, Santosh K
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p. 2151 - 2157
(2016/01/12)
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- Camphorquinone: A new and efficient oxidant for the preparation of 2-thio-substituted benzothiazoles from alcohols by oxidation-reduction condensation
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A convenient one-pot procedure for the preparation of various 2-thio-substituted benzothiazoles from alcohols and benzothiazole-2-thiol utilizing camphorquinone-mediated oxidation-reduction condensation is disclosed. The condensation between benzothiazole-2-thiol and alkyl diphenylphosphinites, generated in situ from alcohols and chlorodiphenylphosphine, proceeded smoothly in the presence of camphorquinone to furnish the corresponding benzothiazoles in good to moderate yields.
- Pluempanupat, Wanchai,Temyarasilp, Parinthorn,Widhalm, Michael,Chavasiri, Warinthorn
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p. 418 - 430
(2014/06/10)
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- Synthesis of 2- N / S / C -substituted benzothiazoles via intramolecular cyclative cleavage of benzotriazole ring
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The synthesis of numerous 2-N/S/C-substituted benzothiazoles was achieved from substituted thiocarbonylbenzotriazoles via free-radical intramolecular cyclative cleavage of the benzotriazole ring in the presence of (TMS) 3SiH and AIBN under mild
- Kumar, Dhananjay,Mishra, Bhuwan B.,Tiwari, Vinod K.
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p. 251 - 266
(2014/01/17)
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- Selective approach to thioesters and thioethers via sp3 C-H activation of methylarenes
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Novel C-S cross-dehydrogenative coupling (CDC) approaches for the selective synthesis of thioesters and thioethers have been developed via sp3 C-H activation of methylarenes and subsequent functionalization. The reaction of methylarenes with thiols resulted in thioesters in the presence of a FeBr2/TBHP system, while treatment of methylarenes with thiols in the Pd(OAc)2/O2/TBHP system led to the formation of thioethers. Both the green protocols demonstrate good functional group tolerance and satisfactory yields. This journal is
- Feng,Lu,Cai
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p. 54409 - 54415
(2015/01/16)
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- Lewis acid-catalyzed, copper(II)-mediated synthesis of heteroaryl thioethers under base-free conditions
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A Lewis acid (AgI, NiII, or FeII) catalyzed, CuII-mediated thiolation reaction between heteroarenes and thiols was achieved with good yield under base-free conditions. DMSO could serve as an effective methylthiolation reagent for the synthesis of heterocyclic methyl thioethers.
- Dai, Chao,Xu, Zhaoqing,Huang, Fei,Yu, Zhengkun,Gao, Yan-Feng
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experimental part
p. 4414 - 4419
(2012/06/18)
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- Ring-opening reactions of 1,4-diazabicyclo[2.2.2]octane (DABCO) derived quaternary ammonium salts with phenols and related nucleophiles
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1,4-Diazabicyclo[2.2.2]octane (DABCO) has been evaluated as a starting material for the synthesis of 1-alkyl-4-(2-phenoxyethyl)piperazines and related derivatives. We found that 1-alkyl-1,4-diazabicyclo[2.2.2]octan-1-ium salts, resulting from the alkylation of DABCO, efficiently react with a variety of nucleophiles in polyethyleneglycol (PEG) or diglyme at high temperatures to give piperazine products resulting from the nucleophilic ring-opening reaction. The benzylation side reaction was found to be relevant with softer nucleophiles when using 1-benzyl-1,4-diazabicyclo[2.2.2]octan-1-ium salts, while other types of alkylations were not observed. One-pot methodologies allow for the synthesis of piperazines directly from primary alcohols, alkyl halides or sulfonates, using phenols, or other nucleophile sources, and DABCO. The Royal Society of Chemistry 2012.
- Mara, Nenad,Polanc, Slovenko,Koevar, Marijan
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experimental part
p. 1300 - 1310
(2012/03/07)
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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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p. 632 - 640
(2012/06/01)
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- Structure-activity relationships of 2-benzylsulfanylbenzothiazoles: Synthesis and selective antimycobacterial properties
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A set of 2-benzylsulfanyl derivatives of benzothiazole was synthesized and evaluated for antimicrobial and cytotoxic activities. The biological screening on antimicrobial activity against a panel of Gram-positive and Gramnegative bacteria, yeasts and fung
- Klimesova, Vera,Koi, Jan,Palat, Karel,Stolarikova, Jirina,Dahse, Hans-Martin,Moellmann, Ute
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experimental part
p. 281 - 292
(2012/09/08)
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- Practical synthesis of β-oxo benzo[d]thiazolyl sulfones: Scope and limitations
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In this paper, we discuss our new synthetic approach towards functionalized benzo[d]thiazolyl (BT) sulfones, based on the reunion of alkyl BT sulfones and various electrophiles (e.g. R-CO-X, RO-CO-X, RS-CO-X, Ts-X...). All important aspects of this coupling reaction, including relevant and undesirable side reactions, are evaluated by means of calculations and competitive experiments. The scope and limitations of this method are established. The Royal Society of Chemistry 2012.
- Pospiil, Jii,Robiette, Raphael,Sato, Hitoshi,Debrus, Kevin
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supporting information; experimental part
p. 1225 - 1234
(2012/03/07)
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- Synthesis of 2-thio-substituted benzothiazoles via a domino condensation/S -arylation/heterocyclization process
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Condensation of carbon disulfide with thiols in the presence of K 2CO3 generates carbonotrithioate salts in situ, which undergo coupling with 2-iodoanilines and subsequent intramolecular condensation and elimination under assistance of CuBr to afford 2-thio-substituted benzothiazoles. Both aliphatic and aromatic thiols are compatible with this process, delivering the corresponding heterocycles with good diversity.
- Shi, Liu,Liu, Xiangqian,Zhang, Hui,Jiang, Yongwen,Ma, Dawei
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experimental part
p. 4200 - 4204
(2011/07/31)
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- Practical synthesis of β-acyl and β-alkoxycarbonyl heterocyclic sulfones
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A short and efficient synthesis for β-acyl and β-alkoxycarbonyl heterocyclic sulfones containing benzothiazol (BT) and phenyltetrazol (PT) heterocyclic core is presented here. The method seems to be general and provides the desired C-nucleophiles in very good to excellent yields from readily available starting materials.
- Pospisil, Jiri,Sato, Hitoshi
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supporting information; experimental part
p. 2269 - 2272
(2011/06/11)
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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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- Targeted thiazole orange derivative with folate: Synthesis, fluorescence and in vivo fluorescence imaging
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A Thiazole Orange conjugated with folate derivative was synthesized in two steps. Firstly, folate was coupled with 1-(3-aminopropyl)-4-methylquinolinium bromide to afford folate-methylquinolinium bromide, which then reacted with benzothiazolium to obtain
- Fei, Xuening,Gu, Yingchun,Wang, Yiqi,Meng, Qingyang,Zhang, Baolian
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scheme or table
p. 6983 - 6992
(2011/02/25)
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- Copper(I)-catalyzed cascade synthesis of 2-substituted 1,3-benzothiazoles: Direct access to benzothiazolones
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An efficient cascade process for the preparation of 2-substituted 1,3-benzothiazoles directly from 2-haloaryl isothiocyanates and O or S nucleophiles by a Cu-catalyzed, intramolecular, C-S bond formation has been developed. This cascade method is viable f
- Murru, Siva,Mondal, Pravat,Yella, Ramesh,Patel, Bhisma K.
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experimental part
p. 5406 - 5413
(2010/02/28)
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- Conversion of alcohols to alkyl aryl sulfides by a new type of oxidation-reduction condensation using phenyl diphenylphosphinite
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Preparation of alkyl aryl sulfides from alcohols and arenethiols such as 2-sulfanyl-1,3-benzothiazole (BtzSH) is described by a new type of oxidation-reduction condensation using phenyl diphenylphosphinite (PhOPPh 2) and benzoquinone derivatives or azide compounds. This reaction proceeds under mild and neutral conditions and is applicable to the thioetherification of various alcohols in which the chiral secondary and tertiary alcohols are converted into the corresponding chiral sulfides with almost complete inversion of configuration.
- Kuroda, Kiichi,Maruyama, Yuji,Hayashi, Yujiro,Mukaiyama, Teruaki
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experimental part
p. 381 - 392
(2009/06/28)
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- Triton B-mediated mild, convenient, and efficient method for the selective alkylation of cyclic secondary amines and thiols
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Alkylation of cyclic secondary amines, thiols, and pyridazinones has been demonstrated with alkyl halides using Triton B as base and reaction medium.
- Meshram,Reddy, B. Chennakesava,Goud, P. Ramesh
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experimental part
p. 2297 - 2303
(2009/12/01)
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- Synthesis and biological evaluation of 2-mercapto-1,3-benzothiazole derivatives with potential antimicrobial activity
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The enhancement of bacterial resistance of pathogens to currently available antibiotics constitutes a serious public health threat. So, intensive efforts are underway worldwide to develop new antimicrobial agents. To identify compounds with a potent antimicrobial profile, we designed and synthesized low molecular weight 2-mercaptobenzothiazole derivatives 2a-2l and 3a-3l. Both series were screened for in-vitro antibacterial activity against the representative panel of Gram-positive and Gram-negative bacteria strains. The biological screening identified compounds 2e and 2l as the most active ones showing an interesting antibacterial activity with MIC values of 3.12 μg/mL against Staphylococcus aureus and 25 μg/mL against Escherichia coli, respectively. The replacement of the S-H by the S-Bn moiety resulted in considerable loss of the antibacterial action of the 3a-3l series. The antibiotic action of compounds 2e and 2l was also investigated by testing their activity against some clinical isolates with different antimicrobial resistance profile. Moreover, the involvement of the NorA efflux pump in the antibacterial activity of our molecules was evaluated. Finally, in this paper, we also describe the cytotoxic activity of the most interesting compounds by MTS assay against HeLa and MRC-5 cell lines.
- Franchini, Carlo,Muraglia, Marilena,Corbo, Filomena,Florio, Marco Antonio,Di Mola, Antonia,Rosato, Antonio,Matucci, Rosanna,Nesi, Marta,Van Bambeke, Francoise,Vitali, Cesare
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experimental part
p. 605 - 613
(2009/12/26)
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- Thiazole Orange derivatives: Synthesis, fluorescence properties, and labeling cancer cells
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A series of Thiazole Orange (TO) derivatives were synthesized and modified by introducing different substitutional groups on benzothiazole and 4-methylquinoline All the TO derivatives were confirmed by 1HNMR and MS. TO derivative bearing NHsub
- Fei, Xuening,Gu, Yingchun,Ban, Ying,Liu, Zhijun,Zhang, Baolian
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experimental part
p. 585 - 591
(2009/07/04)
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- The reaction of benzothiazolyl substituted α-phosphorylmethyl sulfoxides with several amines
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We have examined the reactivities of α-phosphorylmethyl benzothiazolyl sulfoxides in the thermolyses and in the presence of several amines, such as aniline, benzylamine, piperidine, morpholine, and pyrrolidine. Thermolyses of the derivatives in the presen
- Morita, Hiroyuki,Tashiro, Shintaro,Takeda, Masahiro,Yamada, Nobuhiko,Sheikh, Md. Chanmiya,Kawaguchi, Hiroyuki
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p. 4496 - 4505
(2008/09/20)
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- Computational studies and reactivity of nucleophiles in benzylation reactions
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The nucleophilic substitution reactions of benzyl bromide using 2-mercapto benzimidazole, 2-mercaptobenzoxazole and 2-mercaptobenzothiazole as nucleophiles have been studied in methanol and acetone media. The higher reactivity of 2-mercaptobenzimidazole is attributed to the presence of two nitrogen atoms holding a pair of electrons on either side of the >C=S group. The heat of formation, ΔHf, computed from AM1 studies indicates that the reactivity of the nucleophiles is related to ΔHf, and HOMO-LUMO gap of the nucleophile.
- Ranga Reddy,Kalyani,Rajeswara Rao,Manikyamba
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p. 236 - 239
(2008/09/18)
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- Oligomeric benzylsulfonium salts: Facile benzylation via high-load ROMP reagents
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(Chemical Equation Presented) The development of high-load, oligomeric benzylsulfonium salts, generated via ring-opening metathesis polymerization, and their utility in facile benzylations of various nucleophiles is reported. These oligomeric sulfonium salts exist as free-flowing powders and are stable at room temperature. After the benzylation event, purification is attained via simple dry load/filtration, followed by solvent removal to deliver products in excellent yield and purity.
- Zhang, Mianji,Flynn, Daniel L.,Hanson, Paul R.
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p. 3194 - 3198
(2008/02/04)
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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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- Correlation analysis in the benzylation of sulfur nucleophiles
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In the nucleophilic substitution reaction of benzyl bromides with three sulfur nucleophiles a linear relationship between the nucleophile discrimination parameter (s) and the Hammett substituent constant (σ) is observed.
- Kalyani,Manikyamba
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p. 115 - 116
(2008/02/02)
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- High-yield synthesis of fluorinated benzothiazolyl sulfones: General synthons for fluoro-Julia olefinations
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General, high-yield tandem electrophilic fluorination and modified Julia olefination for the synthesis of fluoro olefins is reported. A series of α-fluoro 1,3-benzothiazol-2-yl sulfone-based synthons were synthesized via deprotonation-fluorination. Of critical importance for high-yield fluorinations were heterogeneous reaction conditions, as under homogeneous conditions only starting sulfones were recovered. The α-fluoro 1,3-benzothiazol-2-yl sulfones so obtained were subjected to condensations with a variety of aldehydes and ketones to afford high yields of regiospecifically fluorinated olefins.
- Ghosh, Arun K.,Zajc, Barbara
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p. 1553 - 1556
(2007/10/03)
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- A convenient method for the preparation of alkyl aryl sulfides from alcohols and (chloromethylene)dimethylammonium chloride
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(Chloromethylene)dimethylammonium chloride (Vilsmeier reagent), prepared easily from DMF and oxalyl chloride, works as an efficient condensation reagent for the thioetherification of alcohols in one-pot under mild conditions. Various alcohols are successively converted into the corresponding sulfides with inversion of configurations in moderate to high yields. Copyright
- Kawano, Yoshikazu,Kaneko, Nobuya,Mukaiyama, Teruaki
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p. 1612 - 1613
(2007/10/03)
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- CsF-Celite, an efficient solid state reagent for the syntheses of thioesters and thioethers
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Coupling reactions of a number of aliphatic, aromatic, and heterocyclic compounds bearing an acidic hydrogen atom attached to sulfur, with alkyl, acyl, benzyl, or benzoyl halides in acetonitrile with cesium fluoride-Celite are described. This procedure is convenient, efficient, and practical for the preparation of thioethers and thioesters. Springer-Verlag 2005.
- Shah, Syed T. A.,Khan, Khalid M.,Hussain, Hidayat,Hayat, Safdar,Voelter, Wolfgang
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p. 1583 - 1589
(2007/10/03)
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- A new method for the preparation of alkyl aryl sulfides from alcohols via alkoxydiphenylphosphines by oxidation-reduction condensation
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A new method for the preparation of alkyl aryl sulfides from alcohols via alkoxydiphenylphosphines by oxidation-reduction condensation was established. Various primary, secondary, and tertiary alcohols were successfully converted into the corresponding su
- Mukaiyama, Teruaki,Ikegai, Kazuhiro
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p. 1522 - 1523
(2007/10/03)
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- Heterocyclic benzazole derivatives with antimycobacterial in vitro activity.
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The series of 2-benzylsulfanyl derivatives of benzoxazole and benzothiazole were synthesized, evaluated for their in vitro antimycobacterial activity against Mycobacterium tuberculosis and non-tuberculous mycobacteria, and the activity expressed as the minimum inhibitory concentration (MIC) in micromol/L. The substances bearing two nitro groups (4e, 4f, 5e, 5f) or a thioamide group (4i, 4j, 5i, 5j) exhibited appreciable activity particularly against non-tuberculous strains. The most active compounds were subjected to the toxicity assay and were evaluated as moderately cytotoxic.
- Koci, Jan,Klimesova, Vera,Waisser, Karel,Kaustova, Jarmila,Dahse, Hans-Martin,Moellmann, Ute
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p. 3275 - 3278
(2007/10/03)
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