73006-65-2Relevant academic research and scientific papers
DDQ-Catalyzed Direct C(sp3)-H Amination of Alkylheteroarenes: Synthesis of Biheteroarenes under Aerobic and Metal-Free Conditions
Song, Chunlan,Dong, Xin,Yi, Hong,Chiang, Chien-Wei,Lei, Aiwen
, p. 2195 - 2199 (2018)
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
B(C6F5)3-Catalyzed site-selective N1-alkylation of benzotriazoles with diazoalkanes
Guo, Jing,Mandal, Dipendu,Stephan, Douglas W.,Wu, Yile,Zhao, Yunbo
supporting information, p. 7758 - 7761 (2021/08/13)
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.
Metal-free cross-dehydrogenative C–N coupling of azoles with xanthenes and related activated arylmethylenes
Li, Yanni,Li, Yanping,Li, Yuan,Chen, Chunlin,Ying, Fengyuan,Dong, Ying,Liang, Deqiang
supporting information, p. 2053 - 2065 (2019/05/29)
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
Benzylic C(sp3)-H Functionalization for C-N and C-O Bond Formation via Visible Light Photoredox Catalysis
Pandey, Ganesh,Laha, Ramkrishna,Singh, Deepak
, p. 7161 - 7171 (2016/08/30)
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.
Reusable ionic liquid-catalyzed oxidative coupling of azoles and benzylic compounds via sp3 C-N bond formation under metal-free conditions
Liu, Wenbo,Liu, Chenjiang,Zhang, Yonghong,Sun, Yadong,Abdukadera, Ablimit,Wang, Bin,Li, He,Ma, Xuecheng,Zhang, Zengpeng
, p. 7154 - 7158 (2015/07/01)
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.
Copper acetoacetonate [Cu(acac)2]/BINAP-promoted Csp 3-N bond formation via reductive coupling of N-tosylhydrazones with anilines
Aziz, Jessy,Brion, Jean-Daniel,Hamze, Abdallah,Alami, Mouad
, p. 2417 - 2429 (2013/10/01)
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.
TBHP/I2-promoted oxidative coupling of azoles with benzyl compounds via cleavage of nonactivated C(sp3)-H bonds under solvent-free conditions
Liu, Xiang,Yu, Guiqin,Li, Jihui,Wang, Dong,Chen, Yongxin,Shi, Keqin,Chen, Baohua
supporting information, p. 1588 - 1594 (2013/08/23)
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.
Iron(III)-catalyzed direct N-alkylation of azoles via oxidative transformation of sp3 ci£h bonds under solvent-free conditions
Liu, Xiang,Chen, Yongxin,Li, Kangning,Wang, Dong,Chen, Baohua
, p. 2285 - 2291,7 (2020/09/16)
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
Design, synthesis and antifungal activity of some new imidazole and triazole derivatives
Rezaei, Zahra,Khabnadideh, Soghra,Zomorodian, Kamiar,Pakshir, Kyvan,Kashi, Giti,Sanagoei, Narges,Gholami, Sanaz
experimental part, p. 658 - 665 (2012/06/29)
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
Surfactant-type Bronsted acid catalyzed dehydrative nucleophilic substitutions of alcohols in water
Shirakawa, Seiji,Kobayashi, Shu
, p. 311 - 314 (2007/10/03)
(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
