- One-pot, two-step synthesis of 7-methylene-1,5-piperazine-fused 1,2,3-triazoles
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A facile, one-pot two-step synthesis of 7-methylene-1,5-piperazine-fused 1,2,3-triazole derivatives has been developed. The protocol employs an N-allylation of N-propargylated amines with 2,3-dibromopropene in the presence of K2CO3 in DMSO and a CuI-catalyzed [3 + 2] cycloaddition reaction of the synthetic N-(2-bromoallyl)-N-propargyl amines with sodium azide sequentially. Such a method provides methylene-substituted 1,2,3-triazole fused piperazines with some advantages such as simple operation, high efficiency and good product yield (80–91%) through readily available starting materials.
- Kuang, Lu,Ming, Peng,Wan, Chang-Feng,Chen, Jun-Min,Sheng, Shou-Ri
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p. 563 - 569
(2020/11/19)
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- Synthesis and biological evaluation of coumarin-linked 4-anilinomethyl-1,2,3-triazoles as potent inhibitors of carbonic anhydrases ix and xiii involved in tumorigenesis
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A series of coumarin-linked 4-anilinomethyl-1,2,3-triazoles (6a–t) was synthesized via a molecular hybridization approach, through carbon C-6 of the coumarin moiety. The synthesized compounds were evaluated for their inhibition of carbonic anhydrase (CA)
- Thacker, Pavitra S.,Tiwari, Prerna L.,Angeli, Andrea,Srikanth, Danaboina,Swain, Baijayantimala,Arifuddin, Mohammed,Supuran, Claudiu T.
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- Stereoselective Synthesis of Hexahydroimidazo[1,2- a]quinolines via SN2-Type Ring-Opening Hydroarylation-Hydroamination Cascade Cyclization of Activated Aziridines with N-Propargylanilines
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A novel synthetic approach for the construction of 1,2,3,3a,4,5-hexahydroimidazo[1,2-a]quinolines in good yields (up to 75%) with excellent stereoselectivity (dr up to 94:6, ee up to >99%) under one-pot domino ring-opening cyclization (DROC) conditions ha
- Bhattacharyya, Aditya,Chauhan, Navya,Ghorai, Manas K.,Pradhan, Sajan,Shahi, Chandan K.
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supporting information
p. 7903 - 7908
(2020/11/02)
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- Highly Efficient Conversion of Propargylic Amines and CO2 Catalyzed by Noble-Metal-Free [Zn116] Nanocages
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The reaction of propargylic amines and CO2 can provide high-value-added chemical products. However, most of catalysts in such reactions employ noble metals to obtain high yield, and it is important to seek eco-friendly noble-metal-free MOFs catalysts. Here, a giant and lantern-like [Zn116] nanocage in zinc-tetrazole 3D framework [Zn22(Trz)8(OH)12(H2O)9?8 H2O]n Trz=(C4N12O)4? (1) was obtained and structurally characterized. It consists of six [Zn14O21] clusters and eight [Zn4O4] clusters. To our knowledge, this is the highest-nuclearity nanocages constructed by Zn-clusters as building blocks to date. Importantly, catalytic investigations reveal that 1 can efficiently catalyze the cycloaddition of propargylic amines with CO2, exclusively affording various 2-oxazolidinones under mild conditions. It is the first eco-friendly noble-metal-free MOFs catalyst for the cyclization of propargylic amines with CO2. DFT calculations uncover that ZnII ions can efficiently activate both C≡C bonds of propargylic amines and CO2 by coordination interaction. NMR and FTIR spectroscopy further prove that Zn-clusters play an important role in activating C≡C bonds of propargylic amines. Furthermore, the electronic properties of related reactants, intermediates and products can help to understand the basic reaction mechanism and crucial role of catalyst 1.
- Cao, Chun-Shuai,Cheng, Peng,He, Liang-Nian,Shi, Ying,Song, Zhen-Jun,Xia, Shu-Mei,Xu, Hang,Zhao, Bin
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supporting information
p. 8586 - 8593
(2020/03/26)
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- Zinc(ii)-catalyzed intramolecular hydroarylation-redox cross-dehydrogenative coupling of N -propargylanilines with diverse carbon pronucleophiles: Facile access to functionalized tetrahydroquinolines
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Zinc(ii)-catalyzed intramolecular hydroarylation-redox cross-dehydrogenative coupling of N-propargylanilines with two types of carbon pronucleophiles (nitromethane as a sp3 carbon pronucleophile and phenylacetylenes as sp carbon pronucleophiles) proceeded to give the 2-substituted tetrahydroquinolines in good yields with 100percent atomic utilization without any additional external oxidants.
- Li, Guangzhe,Wang, Chengdong,Li, Yueqing,Shao, Kun,Yu, Guo,Wang, Shisheng,Guo, Xiuhan,Zhao, Weijie,Nakamura, Hiroyuki
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supporting information
p. 7333 - 7336
(2020/07/23)
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- Synthesis and Activity of 1,2,3-Triazole Aminopyrimidines against Cyanobacteria as PDHc-E1 Competitive Inhibitors
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Cyanobacteria harmful algal blooms are of global concern, but all currently available algicides in the market are nonselective and have potential side effects on nontarget species. In the present work, two series of compounds (4 and 6) comprising 16 novel
- Zhou, Yuan,Feng, Jiangtao,Feng, Lingling,Xie, Dan,Peng, Hao,Cai, Meng,He, Hongwu
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p. 12538 - 12546
(2019/11/13)
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- Stereospecific Ring Opening and Cycloisomerization of Aziridines with Propargylamines: Synthesis of Functionalized Piperazines and Tetrahydropyrazines
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Stereospecific Cu-catalyzed nucleophilic ring opening of N-sulfonylaziridines with propargylamines and subsequent hydroamination afford piperazines, which leads to double-bond isomerization to furnish tetrahydropyrazines. Optically active aziridines can be cross-coupled with high enantiomeric purities (>98% ee).
- Das, Bijay Ketan,Pradhan, Sourav,Punniyamurthy, Tharmalingam
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supporting information
p. 4444 - 4448
(2018/08/07)
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- One-pot preparation of pyrrole derivatives via the copper-catalyzed [4+1] annulation of propargylic amines with ethyl glyoxylate and phenylglyoxal in the presence of piperidine
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We describe how copper(II) chloride efficiently catalyzes the [4+1] annulation of propargylamines with either ethyl glyoxylate or phenylglyoxal functioning as a C1 unit, in the presence of piperidine, which leads to a straightforward and one-pot preparati
- Sakai, Norio,Suzuki, Hiroki,Hori, Hiroaki,Ogiwara, Yohei
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supporting information
p. 63 - 66
(2016/12/23)
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- Synthesis of new 1,2,3-triazole linked benzimidazole molecules as anti-proliferative agents
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One pot click chemistry is used to link triazole and benzimidazole pharmacophore to get N-((1-((1H-benzo[d]imidazol-2-yl)methyl)-1H-1,2,3-triazol-4-yl)methyl)aniline and its derivatives. Flexible linkages in the form of –CH2–R or –O–R/–N–R were designed during synthesis. All the newly synthesized compounds were characterized by FT-IR and NMR spectroscopy as well as high-resolution mass spectrometry. Selected compounds were screened for in vitro anti-proliferative activity using National Cancer Institute (NCI)-60 human tumor cell line screening program. The most potent structure N-((1-((1H-benzo[d]imidazol-2-yl)methyl)-1H-1,2,3-triazol-4-yl)methyl)-4-chloroaniline 7e showed 40% growth inhibition in renal cancer cell line (UO-31) at 10 μM concentration.
- Sahay, Ishani I.,Ghalsasi, Prasanna S.
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supporting information
p. 825 - 834
(2017/04/06)
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- Synthesis of 2-Indolyltetrahydroquinolines by Zinc(II)-Catalyzed Intramolecular Hydroarylation-Redox Cross-Dehydrogenative Coupling of N-Propargylanilines with Indoles
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An intramolecular hydroarylation-redox cross-dehydrogenative coupling (CDC) of propargylic anilines with indoles proceeded in the presence of zinc(II) catalysts to give 2-indolyltetrahydroquinolines in good to high yields. Three C-H bonds (two sp2and one sp3) are activated in one shot and these hydrogen atoms are trapped by a propargylic triple bond in the molecule.
- Li, Guangzhe,Nakamura, Hiroyuki
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supporting information
p. 6758 - 6761
(2016/06/09)
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- AgNO2 as the NO Source for the Synthesis of Substituted Pyrazole N-Oxides from N-Propargylamines
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A straightforward method for synthesizing the pyrazole N-oxides from N-propargylamines and AgNO2 through oxidation/cyclization reaction had been developed. AgNO2 was used as the NO source for the first time to synthesize pyrazole N-o
- Yuan, Bingxiang,Zhang, Fuming,Li, Zhuomei,Yang, Shenghua,Yan, Rulong
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supporting information
p. 5928 - 5931
(2016/11/29)
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- Copper(II)-Catalyzed [4+1] annulation of propargylamines with N,O-acetals: Entry to the synthesis of polysubstituted pyrrole derivatives
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Described herein is the CuCl2-catalyzed [4+1] annulation of a variety of propargylamines with N,O-acetals that function as a C1 unit, leading to the production of polysubstituted pyrrole derivatives. Three important features of the N,O-acetal during the [4+1] annulation series via 5-endo-dig cyclization are described: an enolizable substituent adjacent to the central sp3-carbon is required, the central sp3-carbon displays the functions of both an electrophile and a nucleophile, and liberation of the secondary amine smoothly leads to the aromatization. A CuCl2-catalyzed [4+1] annulation of propargylamines with N,O-acetals having an ester, a ketone, and an amide moiety, leading to the facile preparation of polysubstituted pyrrole derivatives is presented. This annulation series was achieved through 5-endo-dig cyclization and subsequent aromatization in one pot.
- Sakai, Norio,Hori, Hiroaki,Ogiwara, Yohei
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supporting information
p. 1905 - 1909
(2015/03/18)
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- A microwave-assisted three-component synthesis of arylaminomethyl ?acetylenes: A facile access to terminal alkynes
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A simple, rapid, one-pot synthesis of arylaminomethyl acetylenes is achieved under microwave-assisted conditions (power? =? 5 W) using aromatic boronic acids, aqueous ammonia, propargyl halides, copper(I) oxide and water as the solvent. The reactions are complete within ten minutes affording good to excellent yields of the products. Georg Thieme Verlag Stuttgart. New York.
- Jiang, Yubo,Huang, Shaojun
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supporting information
p. 407 - 410
(2014/03/21)
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- One-pot synthesis of N-aryl propargylamine from aromatic boronic acid, aqueous ammonia, and propargyl bromide under microwave-assisted conditions
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A facile, one-pot synthesis of N-aryl propargylamine from aromatic boronic acid, aqueous ammonia, and propargyl bromide has been achieved under microwave-assisted conditions. The reactions can be smoothly completed within a total 10 min through a two-step procedure, including copper-catalyzed coupling of aromatic boronic acids with aqueous ammonia and following propargylation by propargyl bromide.
- Jiang, Yu-Bo,Zhang, Wen-Sheng,Cheng, Hui-Ling,Liu, Yu-Qi,Yang, Rui
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p. 779 - 782
(2014/06/09)
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- Synthesis of substituted 3-indolylimines and indole-3-carboxaldehydes by rhodium(II)-catalyzed annulation
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An efficient Cu/Rh-catalyzed method is proposed for the synthesis of 3-indolylimines from N-propargylanilines through Rh(II)-catalyzed denitrogenative annulation of N-sulfonyl-1,2,3-triazoles. Further combined with hydrolysis or reduction, a one-pot method is developed to enable the direct incorporation of an imine, aldehyde, or amine group into an indole system from an alkyne. A variety of substituted 3-indolylimines, indole-3-carboxaldehydes, and 3-Indolylmethanamines are synthesized in good yields.
- Rajagopal, Basker,Chou, Chih-Hung,Chung, Ching-Cheng,Lin, Po-Chiao
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supporting information
p. 3752 - 3755
(2014/08/05)
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- Ln[N(SiMe3)2]3-Catalyzed Cross-Diinsertion of C≡N/C≡C into an N-H Bond: Facile Synthesis of 1,2,4-Trisubstituted Imidazoles from Propargylamines and Nitriles
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A lanthanide-catalyzed sequential insertion of C≡N and C≡C into an N-H bond is presented. The convenient reaction, which proceeds under mild conditions, is an efficient method for preparing 1,2,4-trisubstituted imidazoles directly from readily available propargylamines and nitriles.
- Hong, Longcheng,Shao, Yinlin,Zhang, Lixin,Zhou, Xigeng
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supporting information
p. 8551 - 8555
(2014/07/21)
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- 2-[N-Alkyl(R-phenyl)-aminomethyl]-3-phenyl-7-trifluoromethylquinoxalines as anticancer agents inhibitors of folate enzymes
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Based on our previous results on the ascertained potent growth inhibition effect against a panel of 60 human tumors cell lines at National Cancer Institute of Bethesda (NCI), we have synthesized a novel series of thirty-one 2-[N-methyl(R-phenyl)-aminomethyl]-3-phenyl-7-trifluoromethylquinoxalines (1-31). The lead compound 1 was previously reported to be endowed with significant inhibition against hDHFR enzyme, with a Ki of 0.2 μM. Docking studies were performed on compound 1 and here reported to predict its binding conformation to human dihydrofolate reductase (hDHFR). All compounds (1-31) were assayed versus hDHFR and human thymidylate synthase (hTS). From the screening emerged that all compounds inhibited hDHFR with Ki values included between 0.2 and 11 μM, while only a few (6, 21, 24, 27, 29) showed great activity and selectivity towards hTS. Evaluation of the anticancer activity was performed by NCI, first against the three cell line panel, and only the most active compounds (17, 21, 24, 26, 27) were evaluated on a panel of 60 human tumor cell lines. Compound 21 was the most active against all cell lines with log GI50 equal to -5.49 and log LC50 equal to -4.19 and maintained significant percent of growth inhibition on seven cancer cell lines at the concentration of 1 μM. Compound 17 was the second most active and moreover showed interesting selectivity against some cell lines (Lung cancer: A549/ATCC, Melanoma: UACC-257, Ovarian Cancer: ovcar-8 and Renal cancer: RXF 393) at all concentration examined (100-0.01 μM).
- Piras, Sandra,Carta, Antonio,Briguglio, Irene,Corona, Paola,Paglietti, Giuseppe,Luciani, Rosaria,Costi, Maria Paola,Ferrari, Stefania
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p. 169 - 183
(2014/03/21)
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- An expedient approach to substituted triazolo[1,5-a][1,4]benzodiazepines via Cu-catalyzed tandem Ullmann C-N coupling/azide-alkyne cycloaddition
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An approach to the synthesis of triazolo[1,5-a][1,4]benzodiazepines comprising copper catalyzed tandem Ullmann C-N coupling followed by azide-alkyne cycloaddition has been described. The reaction of o-azidobenzylbromide and N-propargylated aniline derivat
- Majumdar,Ganai, Sintu
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supporting information
p. 6192 - 6195
(2013/10/22)
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- THIAZOLYLIDINE UREA AND AMIDE DERIVATIVES AND METHODS OF USE THEREOF
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The invention relates to novel thiazolylidine urea and amide derivatives that are PAMs of neuronal nicotinic receptors, compositions comprising the same, processes for preparing such compounds, and methods for using such compounds and compositions.
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Page/Page column 20
(2009/07/10)
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- Intramolecular aromatic substitution and amino-claisen rearrangement in substituted N-(2-propynyl)anilines on electron impact
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N-(2-Propynyl)anilines undergo amino-Claisen rearrangement to a minor extent in the ion source, losing a molecule of HCN under electron impact conditions. However, metastable molecular ions with energies closer to threshold undergo Claisen rearrangement g
- Ramana,Sudha
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p. 1028 - 1033
(2007/10/03)
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- Antiproliferative cyclic compounds
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A compound of formula (I) capable of inhibiting thymidylate synthase, a method for making such and a therapeutic process utilizing the compound of formula (I).
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- SELECTIVE SYNTHESIS OF MONO- AND DIPROPARGYLARYLAMINES ON ALUMINUM OXIDE
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Propargylarylamines are formed with preparative yields in the reaction of propargyl bromide with arylamines in a molar ratio of 1:3 on aluminum oxide.The use of aluminum oxide modified with potassium carbonate and a reduction in the relative amount of the
- Abdulganeeva, S. A.,Erzhanov, K. B.
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p. 466 - 469
(2007/10/02)
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