- DDQ-Catalyzed Direct C(sp3)-H Amination of Alkylheteroarenes: Synthesis of Biheteroarenes under Aerobic and Metal-Free Conditions
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A strategy for oxidative Csp3-H/N-H cross-coupling is presented. This reaction successfully utilizes 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) and tert-butyl nitrite (TBN) as co-catalysts to construct the biomedical applicable biheteroarene
- Song, Chunlan,Dong, Xin,Yi, Hong,Chiang, Chien-Wei,Lei, Aiwen
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- B(C6F5)3-Catalyzed site-selective N1-alkylation of benzotriazoles with diazoalkanes
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Alkylation of benzotriazoles is synthetically challenging, often leading to mixtures of N1 and N2 alkylation. Herein, metal-free catalytic site-selective N1-alkylation of benzotriazoles with diazoalkanes is described in the presence of 10 mol% of B(C6F5)3. These reactions provide N1-alkylated benzotriazoles in good to excellent yields and this protocol is successfully adapted to gram-scale syntheses as well as a derivative with antimicrobial activity.
- Guo, Jing,Mandal, Dipendu,Stephan, Douglas W.,Wu, Yile,Zhao, Yunbo
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supporting information
p. 7758 - 7761
(2021/08/13)
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- Metal-free cross-dehydrogenative C–N coupling of azoles with xanthenes and related activated arylmethylenes
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A metal-free C(sp3)–H/N–H cross-coupling of azoles with xanthenes and related activated arylmethylenes is presented. Both the use of azoles and the activation pattern of C(sp3)–H sources are essential for this transformation. In the
- Li, Yanni,Li, Yanping,Li, Yuan,Chen, Chunlin,Ying, Fengyuan,Dong, Ying,Liang, Deqiang
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supporting information
p. 2053 - 2065
(2019/05/29)
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- Benzylic C(sp3)-H Functionalization for C-N and C-O Bond Formation via Visible Light Photoredox Catalysis
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A visible light mediated highly selective benzylic C-H bond functionalization for intermolecular C-N and C-O bond formation is reported. This cross-dehydrogenative coupling reaction demonstrates a straightforward protocol for incorporating the heteroaromatics to the benzylic position. Benzylic oxidation of various alkyl aryls to corresponding carbonyl compounds has also been reported.
- Pandey, Ganesh,Laha, Ramkrishna,Singh, Deepak
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p. 7161 - 7171
(2016/08/30)
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- Reusable ionic liquid-catalyzed oxidative coupling of azoles and benzylic compounds via sp3 C-N bond formation under metal-free conditions
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The heterocyclic ionic liquid-catalyzed direct oxidative amination of benzylic sp3 C-H bonds via intermolecular sp3 C-N bond formation for the synthesis of N-alkylated azoles under metal-free conditions is reported for the first time. The catalyst 1-butylpyridinium iodide can be recycled and reused with similar efficacies for at least eight cycles.
- Liu, Wenbo,Liu, Chenjiang,Zhang, Yonghong,Sun, Yadong,Abdukadera, Ablimit,Wang, Bin,Li, He,Ma, Xuecheng,Zhang, Zengpeng
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p. 7154 - 7158
(2015/07/01)
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- Copper acetoacetonate [Cu(acac)2]/BINAP-promoted Csp 3-N bond formation via reductive coupling of N-tosylhydrazones with anilines
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We report the the copper(II) acetoacetonate [Cu(acac)2]/BINAP- catalyzed synthesis of arylamines from N-tosylhydrazones and anilines. A fine tuning of the reaction conditions was required to accomplish the cross-coupling successfully, including the ligands effect and the addition of small amounts of water. The characteristic feature of this protocol is its functional group compatibility and its chemoselectivity when various aminophenol derivatives were used. Taking into consideration the interest for this copper-reductive coupling in which no stoichiometric metal hydride reagent is employed, this can be considered as an alternative to the conventional reductive amination.
- Aziz, Jessy,Brion, Jean-Daniel,Hamze, Abdallah,Alami, Mouad
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p. 2417 - 2429
(2013/10/01)
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- TBHP/I2-promoted oxidative coupling of azoles with benzyl compounds via cleavage of nonactivated C(sp3)-H bonds under solvent-free conditions
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A novel and efficient TBHP/I2-promoted oxidative coupling of azoles with benzyl compounds via cleavage of nonactivated C(sp3)-H bonds under metal-free, base-free, and solvent-free conditions for the synthesis of N-alkylated azoles has been developed. The procedure, using I2 as the catalyst, is a simple, economical, and environmentally friendly protocol, which could be applied to various available substrates in moderate to good yields. Georg Thieme Verlag Stuttgart. New York.
- Liu, Xiang,Yu, Guiqin,Li, Jihui,Wang, Dong,Chen, Yongxin,Shi, Keqin,Chen, Baohua
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supporting information
p. 1588 - 1594
(2013/08/23)
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- Iron(III)-catalyzed direct N-alkylation of azoles via oxidative transformation of sp3 ci£h bonds under solvent-free conditions
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A new approach to synthesize N-alkylation of azoles by iron(III)-catalyst under solvent-free conditions was developed. The method is broad in scope and highly efficient. A new approach to synthesize N-alkylation of azoles by iron (III)-catalyst under solv
- Liu, Xiang,Chen, Yongxin,Li, Kangning,Wang, Dong,Chen, Baohua
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p. 2285 - 2291,7
(2020/09/16)
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- Design, synthesis and antifungal activity of some new imidazole and triazole derivatives
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Triazole and imidazole are incorporated into the structures of many antifungal compounds. In this study a novel series of 1,2,4-triazole, imidazole, benzoimidazole, and benzotriazole derivatives was designed as inhibitors of cytochrome P450 14α-demethylase (14DM). These structures were docked into the active site of MT-CYP51, using Autodock program. Sixteen compounds with the best binding energy were synthesized. The chemical structures of the new compounds were confirmed by elemental and spectral (1H-NMR and Mass) analyses. All compounds were investigated for antifungal activity against Candida albicans, Candida tropicalis, Candida glabrata, Candida parapeilosis, Candida kruzei, Candida dubliniensis, Aspergillus fomigatus, Aspergillus flavus, Microsporum canis, Microsporum gypseum, Trichophyton mentagrophyte, Epidermophyton floccosum. Some compounds showed excellent in-vitro antifungal activity against most of the tested fungi. Compounds 2, 9, and 10 had antifungal activity against several resistant fungi against fluconazole and itraconazole. A novel series of azole derivatives was designed and synthesized as inhibitors of cytochrome P450 14α-demethylase and the compounds were investigated for antifungal activity. Copyright
- Rezaei, Zahra,Khabnadideh, Soghra,Zomorodian, Kamiar,Pakshir, Kyvan,Kashi, Giti,Sanagoei, Narges,Gholami, Sanaz
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experimental part
p. 658 - 665
(2012/06/29)
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- Surfactant-type Bronsted acid catalyzed dehydrative nucleophilic substitutions of alcohols in water
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(Chemical Equation Presented) A protocol for the dehydrative nucleophilic substitution of benzyl alcohols with a variety of carbon- and heteroatom-centered nucleophiles using dodecylbenzenesulfonic acid (DBSA) as a surfactant-type Bronsted acid catalyst i
- Shirakawa, Seiji,Kobayashi, Shu
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p. 311 - 314
(2007/10/03)
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- Radical Mediated Synthesis of 6-Arylphenanthridines via Benzotriazole Ring-opening
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Lithiation of diarylbenzotriazol-1-ylmethanes followed by addition of copper(I) iodide gave 6-arylphennathridine derivatives in moderate yields.When the two aryl groups were the same or contained very different electron densities, only one product was obt
- Katritzky, Alan R.,Yang, Baozhen
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p. 607 - 610
(2007/10/03)
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- Studies on the Thermal Isomerization of N-Arylmethylbenzotriazoles
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The thermal isomerizations of N-benzyl-, N-diarylmethyl- and N-trityl-benzotriazole, and of N--, and N-trityl-5,6-dimethylbenzotriazole under nitrogen have been investigated.In all these cases , the N-1 isomer predominates over the N-2 isomer at thermodynamic equilibrium, to an extent which depends on the steric bulk of the N-substituent.The rate of attainment of equilibrium depends on the electronic effects of the substituents, both in the benzotriazole ring and in the migrating group.These results, in conjunction with a cross-over experiment, support a mechanism involving a heterolytic N-C bond cleavage followed by an intermolecular rearrangement.
- Katritzky, Alan R.,Perumal, Subbu,Fan, Wei-Qiang
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p. 2059 - 2062
(2007/10/02)
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- SYNTHESIS BY PHASE TRANSFER CATALYSIS OF N-BENZYL, N-DIPHENYLMETHYL AND N-TRIPHENYLMETHYL AZOLES AND BENZAZOLES: PROTON NMR AND CHROMATOGRAPHIC DATA AS A TOOL FOR IDENTIFICATION
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Pyrazole, imidazole, 1,2,4-triazole, indazole and benzotriazole were alkylated under phase transfer catalysis (PTC) with benzyl-, diphenylmethyl- and trityl chloride.Alkylation occured only at the ring nitrogen atoms of the heterocycle, except for indazole in which substitution took also place at position 3.A systematic study of the N- and C-substituted derivatives by proton NMR and chromatographic techniques has been done.
- Claramunt, Rosa M.,Elguero, Jose,Garceran, Rafael
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p. 2895 - 2906
(2007/10/02)
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