- Photoredox synthesis of functionalized quinazolinesviacopper-catalyzed aerobic oxidative Csp2-H annulation of amidines with terminal alkynes
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We have developed a visible light-induced photo-redox copper-catalyzed oxidative Csp2-H annulation (Friedel-Crafts-type cyclization) of amidines with terminal alkynes at room temperature to synthesize functionalized quinazolines. We report copp
- Charpe, Vaibhav Pramod,Hwang, Kuo Chu,Ragupathi, Ayyakkannu,Sagadevan, Arunachalam
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supporting information
p. 5024 - 5030
(2021/07/29)
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- Synthesis of aminoisoquinolines via Rh-catalyzed [4 + 2] annulation of benzamidamides with vinylene carbonate
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A new strategy is developed for the synthesis of 1-aminoisoquinoline derivatives. This Rh(III)-catalyzed [4 + 2] annulation reaction employs benzamidines as efficient directing groups and the vinylene carbonate as an acetylene surrogate. Additionally, the reaction features broad substrate scopes and good yields, only producing carbonate anion as byproduct.
- Huang, Xin,Xu, Yingying,Li, Jianglian,Lai, Ruizhi,Luo, Yi,Wang, Qiantao,Yang, Zhongzhen,Wu, Yong
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supporting information
p. 3518 - 3521
(2021/06/12)
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- Direct, Late-Stage Mono-N-arylation of Pentamidine: Method Development, Mechanistic Insight, and Expedient Access to Novel Antiparastitics against Diamidine-Resistant Parasites
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A selective mono-N-arylation strategy of amidines under Chan-Lam conditions is described. During the reaction optimization phase, the isolation of a mononuclear Cu(II) complex provided unique mechanistic insight into the operation of Chan-Lam mono-N-arylation. The scope of the process is demonstrated, and then applied to access the first mono-N-arylated analogues of pentamidine. Sub-micromolar activity against kinetoplastid parasites was observed for several analogues with no cross-resistance in pentamidine and diminazene-resistant trypanosome strains and against Leishmania mexicana. A fluorescent mono-N-arylated pentamidine analogue revealed rapid cellular uptake, accumulating in parasite nuclei and the kinetoplasts. The DNA binding capability of the mono-N-arylated pentamidine series was confirmed by UV-melt measurements using AT-rich DNA. This work highlights the potential to use Chan-Lam mono-N-arylation to develop therapeutic leads against diamidine-resistant trypanosomiasis and leishmaniasis.
- Robertson, Jack,Ungogo, Marzuq A.,Aldfer, Mustafa M.,Lemgruber, Leandro,McWhinnie, Fergus S.,Bode, Bela E.,Jones, Katherine L.,Watson, Allan J. B.,de Koning, Harry P.,Burley, Glenn A.
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supporting information
p. 3396 - 3401
(2021/09/06)
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- Transition-Metal-Free Synthesis of 1,2-diphenyl-1H-benzo[d] Imidazole Derivatives from N-phenylbenzimidamides and Cyclohexanones
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A transition-metal-free strategy for the formation of 1,2-diphenyl-1H-benzo[d] imidazoles from N-phenylbenzimidamides and cyclohexanones is introduced. This is the first report on the direct synthesis of 1,2-diphenyl-1H-benzo[d] imidazoles from cyclohexanones and N-phenylbenzimidamides via iodine- promoted oxidative cyclization. Non-aromatic cyclohexanones were smoothly dehydrogenated, and acted as an aryl source using oxygen as a green oxidant. The catalytic use of iodine makes this method quite simple, more economical and convenient. Under optimized conditions, various substituted 1,2-diphenyl-1H-benzo[d] imidazoles were smoothly reacted, and the desired substituted imidazoles were generated with moderate to excellent yields. (Figure presented.).
- Lu, Guoqiang,Luo, Nan,Hu, Fangpeng,Ban, Zihui,Zhan, Zhenzhen,Huang, Guo-Sheng
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supporting information
p. 487 - 492
(2019/12/12)
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- Base-Mediated Amination of Alcohols Using Amidines
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Novel and efficient base-mediated N-alkylation and amidation of amidines with alcohols have been developed, which can be carried out in one-pot reaction conditions, which allows for the synthesis of a wide range of N-alkyl amines and free amides in good to excellent yields with high atom economy. In contrast to borrowing hydrogen/hydrogen autotransfer or oxidative-type N-alkylation reactions, in which alcohols are activated by transition-metal-catalyzed or oxidative aerobic dehydrogenation, the use of amidines provides an effective surrogate of amines. This circumvents the inherent necessity in N-alkylation of an oxidant or a catalyst to be stabilized by ligands.
- Chen, Jianbin,Fang, Yanchen,Jia, Xiaofei,Jiang, Shaohua,Li, Zehua,Liang, Zuyu,Lu, Fenghong,Qi, Shuo,Ren, Chaoyu,Yu, Shuangming,Zhang, Chunyan,Zhang, Guoying,Zhang, Sheng
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p. 7728 - 7738
(2020/07/15)
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- Synthesis of 1,2-dihydro-1,3,5-triazine derivativesviaCu(ii)-catalyzed C(sp3)-H activation ofN,N-dimethylethanolamine with amidines
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1,2-Dihydro-1,3,5-triazines and symmetrical 1,3,5-triazines were obtained in up to 81% yields from amidines andN,N-dimethylethanolamine catalyzed by CuCl2. The reaction involves three C-N bond formations during the oxidative annulation process
- Chen, Rener,Ma, Renchao,Ma, Yongmin,Wang, Lei,Wang, Zhiming,Yan, Min
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supporting information
p. 10946 - 10949
(2020/10/02)
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- Acid-catalyzed synthesis of imidazole derivatives via N-phenylbenzimidamides and sulfoxonium ylides cyclization
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A straightforward method to synthesize imidazole derivatives from amidines and sulfoxonium ylides catalyzed by acids is reported in this study. Specifically, catalyzed by trifluoroacetic acid in DCE solvents can improve synthesis efficiency under metal-fr
- Tian, Yuan,Qin, Mingda,Yang, Xueying,Zhang, Xueguo,Liu, Yafeng,Guo, Xin,Chen, Baohua
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supporting information
p. 2817 - 2823
(2019/04/13)
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- Metal-Free C-B Bond Cleavage: An Acid Catalyzed Three-Component Reaction Construction of Imidazole-Containing Triarylmethanes
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An efficient acid-catalyzed strategy to prepare imidazole-containing triarylmethanes from amidines, ynals, and boronic acids has been developed. It represents an unprecedented and novel metal-free C-B bond cleavage strategy as a workable route to form new carbon-carbon bonds.
- Wang, Changcheng,Yu, Yue,Su, Zhengquan,Li, Xuechen,Cao, Hua
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supporting information
p. 4420 - 4423
(2019/06/27)
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- Vanadium-Catalyzed Oxidative C(CO)-C(CO) Bond Cleavage for C-N Bond Formation: One-Pot Domino Transformation of 1,2-Diketones and Amidines into Imides and Amides
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A novel vanadium-catalyzed one-pot domino reaction of 1,2-diketones with amidines has been identified that enables their transformation into imides and amides. The reaction proceeds by dual acylation of amidines via oxidative C(CO)-C(CO) bond cleavage of 1,2-diketones to afford N,N′-diaroyl-N-arylbenzamidine intermediates. In the reaction, these intermediates are easily hydrolyzed into imides and amides through vanadium catalysis. This method provides a practical, simple, and mild synthetic approach to access a variety of imides as well as amides in high yields. Moreover, one-step construction of imide and amide bonds with a long-chain alkyl group is an attractive feature of this protocol.
- Digwal, Chander Singh,Yadav, Upasana,Ramya, P. V. Sri,Sana, Sravani,Swain, Baijayantimala,Kamal, Ahmed
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p. 7332 - 7345
(2017/07/26)
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- Direct Access to 1,3,5-Trisubstituted 1 H -1,2,4-Triazoles from N -Phenylbenzamidines via Copper-Catalyzed Diamination of Aryl Nitriles
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A copper-catalyzed formation of C-N/N-N bonds using N-phenylbenzamidines with aryl nitriles has been developed and affords a route to 1,3,5-trisubstituted 1H-1,2,4-triazoles in moderate to excellent yields. The method is operationally simple and environme
- Zhang, Lutao,Tang, Dong,Gao, Jing,Wang, Jing,Wu, Ping,Meng, Xu,Chen, Baohua
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p. 3924 - 3930
(2016/11/11)
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- Synthesis of 2-arylquinazolin-4(3H)-ones by N-aryl benzamidines with aromatic carbonates
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The reaction of N-aryl benzamidines 1a, 1b, 1c, 1d, 1e, 1f, 1g, 1h, 1i, 1j, 1k, 1l, 1m, 1n with diphenyl carbonate 2a or ethyl phenyl carbonate 2b synthesized 2-arylquinazolin-4(3H)-ones 3a, 3b, 3c, 3d, 3e, 3f, 3g, 3h, 3i, 3j, 3k, 3l, 3m, 3n in simple and
- Aikawa, Shunichi,Sekiguchi, Chiharu,Yamazaki, Yuko,Hattori, Mika,Isaka, Tatsuya,Yoshida, Yasuhiko,Ihara, Shogo
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p. 343 - 348
(2014/04/17)
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- Copper-catalyzed three-component synthesis of 3-Aminopyrazoles and 4-iminopyrimidines via β-alkynyl-N-sulfonyl ketenimine intermediates
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3-Aminopyrazoles and 4-iminopyrimidines were efficiently prepared via copper-catalyzed three-component reactions of butadiynes, sulfonylazides, and hydrazides or imidamides. The reactions were regioselectively approached via the formation of a β-alkynyl-N-sulfonyl ketenimine intermediate which represented a new and effective 1,3-dielectrophilic equivalent in organic synthesis.
- Xing, Yanpeng,Cheng, Binyu,Wang, Jing,Lu, Ping,Wang, Yanguang
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supporting information
p. 4814 - 4817
(2015/04/27)
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- Synthesis of benzimidazoles by PIDA-promoted direct C(sp2)-H imidation of N-arylamidines
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A metal-free synthesis of diversified benzimidazoles from N-arylamidines through a phenyliodine(III) diacetate (PIDA) promoted intramolecular direct C(sp2)-H imidation has been developed. The reaction proceeds smoothly at 0 °C or ambient temperature to provide the desired products in good to excellent yields. The synthesis of 2-alkyl- or 2-alkyl-fused benzimidazoles, which are generally inaccessible by similar Pd- or Cu-catalyzed approaches, can also be achieved. Copyright
- Huang, Jinbo,He, Yimiao,Wang, Yong,Zhu, Qiang
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supporting information
p. 13964 - 13967
(2013/01/15)
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- Palladium-catalyzed intramolecular C(sp2)-H amidination by isonitrile insertion provides direct access to 4-aminoquinazolines from N-arylamidines
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An efficient method for the synthesis of 4-amino-2-aryl(alkyl)quinazolines from readily available N-arylamidines and isonitriles via palladium-catalyzed intramolecular aryl C-H amidination by isonitrile insertion has been developed.
- Wang, Yong,Wang, Honggen,Peng, Jiangling,Zhu, Qiang
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supporting information; experimental part
p. 4604 - 4607
(2011/10/12)
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- Regiospecific synthesis of 1, 2-disubstituted (hetero)aryl fused imidazoles with tunable fluorescent emission
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A palladium-catalyzed two or fourfold amination was established that allows regiospecific synthesis of a diversity-oriented library of 1, 2 disubstituted (hetero)aryl fused imidazoles, and provides an exceptional tool for the discovery of fluorescent scaf
- Zhao, Dongbing,Hu, Junyi,Wu, Ningjie,Huang, Xiaolei,Qin, Xurong,Lan, Jingbo,You, Jingsong
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supporting information; experimental part
p. 6516 - 6519
(2012/02/02)
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- An efficient route towards the synthesis of monosubstituted N-aryl amidines from 4,5-Dihydro-1,2,4-oxadiazoles
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4,5-Dihydro-1,2,4-oxadiazoles were prepared using 1,3-dipolar cycloaddition of imines with nitrile oxides. Further reductive N-O bond cleavage furnished monosubstituted N-aryl amidines in good yield. Thus an efficient route for the synthesis of monosubsti
- Chavan, Neelam L.,Naik, Nilesh H.,Nayak, Sandip K.,Kusurkar, Radhika S.
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experimental part
p. 248 - 255
(2010/08/07)
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- Direct imidation to construct 1H-benzo[d]imidazole through Pd II-catalyzed C-H activation promoted by thiourea
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A study was conducted to demonstrate the development of a method to construct 1H-benzo[d]immidazole through PdII -catalyzed intermolecular C-H activation starting from N-phenylbenziimidamide. The detailed mechanism investigations indicated that a palladacycle monomer or dimer was the key intermediate for this transformation, demonstrating that thiourea was first used to influence the efficiency of C-H activation. The method was found to construct 1H-benzo[d]immidazole through PdII -catalyzed intermolecular C-H activation extending the substrate scope widely. It also demonstrated the introduction of thiourea (tetramethylthiourea) (TMTU) for the first time as an additive to promote the efficiency of PdII catalysis for the direct C-H transformation. N-phenylbenziimidamide was also readily synthesized through the addition of aniline to benzonitrile according to the method to conduct the investigations.
- Xiao, Qing,Wang, Wen-Hua,Liu, Gang,Meng, Fan-Ke,Chen, Jia-Hua,Yang, Zhen,Shi, Zhang-Jie
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supporting information; experimental part
p. 7292 - 7296
(2010/03/24)
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- Synthesis, structure-activity relationships at the GABAA receptor in rat brain, and differential electrophysiological profile at the recombinant human GABAA receptor of a series of substituted 1,2-diphenylimidazoles
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A series of new 1,2-diphenylimidazole derivatives (1a-x) were synthesized and evaluated for their ability to potentiate γ-aminobutyric acid (GABA)-evoked currents in Xenopus laevis oocytes expressing recombinant human GABAA receptors. Many of t
- Asproni, Battistina,Talani, Giuseppe,Busonero, Fabio,Pau, Amedeo,Sanna, Sebastiano,Cerri, Riccardo,Mascia, Maria Paola,Sanna, Enrico,Biggio, Giovanni
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p. 2638 - 2645
(2007/10/03)
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- Samarium(II) iodide induced reductive coupling of nitriles with nitro compounds
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The intermolecular and intramolecular reductive coupling of a cyano group with a nitro group induced by SmI2 was studied. Amidines and 2-aminoquinoline derivatives are prepared in good yields under neutral and mild conditions respectively.
- Zhou, Longhu,Zhang, Yongmin
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p. 2899 - 2902
(2007/10/03)
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- Facile Synthesis of Amidines via the Intermolecular Reductive Coupling of Nitriles with Nitro Compounds Induced by Samarium(II) Iodide
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The intermolecular reductive coupling of nitriles with nitro compounds induced by Sml2 was studied; amidine derivatives are prepared in good yields under neutral and mild conditions.
- Zhou, Longhu,Zhang, Yongmin
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p. 596 - 597
(2007/10/03)
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- Low-valent titanium induced reductive coupling of nitriles with nitro compounds
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The intermolecular and intramolecular reductive coupling of a cyano group with a nitro group induced by a low-valent titanium reagent prepared from TiCl4/Sm was studied. Amidines and 2-aminoquinolines derivatives are prepared in good yields under mild conditions respectively.
- Zhou, Longhu,Zhang, Yongmin
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p. 3249 - 3262
(2007/10/03)
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- Reaction of Sulphuryl Chloride with Some Schiff Bases
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The reaction of sulphuryl chloride with schiff bases has been studied.In each case, pure crystalline products have been isolated, and their structures elucidated on the basis of IR, PMR and mass spectral data.A plausible mechanism is advanced for the formation of observed products.
- Dhar, Durga N.,Gupta, Sudha R.
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p. 533 - 535
(2007/10/02)
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