- 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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- 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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- 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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- 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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- 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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- Preparation and in vitro evaluation of benzylsulfanyl benzoxazole derivatives as potential antituberculosis agents
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A set of 2-benzylsulfanyl derivatives of benzoxazole was synthesized and evaluated for their in vitro antimycobacterial activity against Mycobacterium tuberculosis, non-tuberculous mycobacteria and multidrug-resistant M. tuberculosis. The activities were
- Klimesova, Vera,Koci, Jan,Waisser, Karel,Kaustova, Jarmila,Moellmann, Ute
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experimental part
p. 2286 - 2293
(2009/09/06)
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- Unexpected orthogonality of S-benzoxazolyl and S-thiazolinyl glycosides: Application to expeditious oligosaccharide assembly
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Thorough mechanistic studies of the alkylation pathway for the activation of glycosyl thioimidates have led to the development of the " thioimidateonly orthogonal strategy". Discrimination among S-thiazolinyl (STaz) and S-benzoxazolyl (SBox) anomeric leav
- Kaeothip, Sophon,Pornsuriyasak, Papapida,Rath, Nigam P.,Demchenko, Alexei V.
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supporting information; experimental part
p. 799 - 802
(2009/09/05)
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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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- 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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- 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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- One-Flask Synthesis of Sulfides from Alcohols and Alkyl Halides Using Benzoxazoline-2-thione
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The synthesis of sulfides from alcohols and benzoxazoline-2-thione (I) was studied to establish its generality and the mechanism of the reaction.A one-flask synthesis of sulfides from alcohols was developed.According to this procedure, various sulfides were prepared without the use of illsmelling thiols.Moreover, partial sulfenylation of diols to give sulfenyl alcohols was achieved.Keywords - one-flask synthesis; benzoxazoline-2-thione; partial sulfenylation; sulfide; sulfenyl alcohol
- Takeuchi, Yasuo,Sakagawa, Keiko,Kubo, Masumi,Yamato, Masatoshi
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p. 1323 - 1327
(2007/10/02)
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- Synthesis of 3-Substitued Benzoxazoline-2-thiones
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Several methods for the preparation of 3-substitued benzoxazoline-2-hiones (1) were examined.Method B via the thiation of 3-substitued benzoxazoline-2-one (5) with phosphorus pentasulfide was found to be applicable to the preparation of most analogs of 1, with a few expections.Method C via the cyclization of 2-(alkylamino)phenol (7) with potassium O-methyldithiocarbonate was suitable for the preparation of analogs with a group sensitive to high temperature of with an aryl- (including aromatic heterocyclic ring) methyl group.In addition, the reaction of benzoxazoline-2-thione (2) with acetals such as 1-ethoxyisochroman, 2-ethoxytetrahydrofuran, and ethoxytetraydropyran, or with Michael acceptors such as 2,3-dihydrofuran and 2H-3,4-dihydropyran, gave 3-substitued benzoxazoline-2-thione (1d-f).
- Yamato, Masatoshi,Takeuchi, Yasuo,Hashigaki, Kuniko,Hattori, Kyoko,Muroga, Eiko,Hirota, Takashi
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p. 1733 - 1737
(2007/10/02)
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