- Preparation of polystyrene-supported vinyl sulfone and its application in the solid-phase organic synthesis of 1-monosubstituted 1,2,3-triazoles
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A polystyrene-supported vinyl sulfone reagent was prepared and used for the solid-phase organic synthesis of 1-monosubstituted 1,2,3-triazoles via a 1,3-dipolar cycloaddition reaction with azides and subsequent cleavage from the polymer support through an elimination reaction in the presence of potassium tert-butoxide. The advantages of this method include straightforward operation, good yield and high purity of the crude products.
- Huang, Zhenzhong,Wang, Ruiling,Sheng, Shouri,Zhou, Ruyi,Cai, Mingzhong
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Read Online
- [4 + 1] Annulation of in situ generated azoalkenes with amines: A powerful approach to access 1-substituted 1,2,3-triazoles
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1-Substituted 1,2,3-triazoles represents ‘privileged’ structural scaffolds of many clinical pharmaceuticals. However, the traditional methods for their preparation mainly rely on thermal [3 + 2] cycloaddition of potentially dangerous acetylene and azides. Here we report a base-mediated [4 + 1] annulation of azoalkenes generated in situ from readily available difluoroacetaldehyde N-tosylhydrazones (DFHZ-Ts) with amines under relatively mild conditions. This azide- and acetylene-free strategy provides facile access to diverse 1-substituted 1,2,3-triazole derivatives in high yield in a regiospecific manner. This transformation has great functional group tolerance and can suit a broad substrate scope. Furthermore, the application of this novel methodology in the gram-scale synthesis of an antibiotic drug PH-027 and in the late-stage derivatization of several bioactive small molecules and clinical drugs demonstrated its generality, practicability and applicability.
- Bi, Xihe,Ning, Yongquan,Sivaguru, Paramasivam,Wang, Hongwei,Zanoni, Giuseppe
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supporting information
(2021/09/30)
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- Microwave-assisted one-pot quick synthesis of 1-monosubstituted 1,2,3-triazoles from arylboronic acids, sodium azide and 3-butyn-2-ols
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Abstract: Microwave-assisted one-pot quick synthesis to 1-monosubstituted 1,2,3-triazoles was achieved with good to excellent yields using the widely available arylboronic acids, sodium azide and 3-butyn-2-ols within 15 min. This method features high effi
- Du, Zhonglin,Li, Fenrui,Li, Li,Li, Ran
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- An azide and acetylene free synthesis of 1-substituted 1,2,3-triazoles
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This paper details a simple and efficient 3-component synthesis of 1-substituted 1,2,3-triazoles using a primary amine, 2,2-dimethoxyacetaldehyde and tosylhydrazide. The reaction proceeds in good to excellent yields using either aliphatic or aromatic amine substrates and is tolerant of a wide range of functional groups including electron-rich and deficient aryl groups, terminal alkynes, ketones and highly sterically encumbered amines.
- Patterson, Sarah J.M.,Clark, Peter R.,Williams, Glynn D.,Tomkinson, Nicholas C.O.
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supporting information
(2020/10/13)
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- One-Pot Synthesis of 1-Monosubstituted 1,2,3-Triazoles from Propargyl Alcohol
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A one-pot synthesis of 1-monosubstituted-1,2,3-triazoles from propargyl alcohol and various aryl azides was achieved. This simple method provides concise and efficient access to various 1-monosubstituted 1,2,3-triazole derivatives through a three-step one
- Han, Chunmei,Dong, Suping,Zhang, Wensheng,Chen, Zhen
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p. 673 - 677
(2018/03/10)
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- One-pot synthesis of 1-monosubstituted-1, 2, 3-triazoles from 2-methyl-3-butyn-2-ol
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An efficient method for the synthesis of 1-monosubstituted-1, 2, 3-triazoles from 2-methyl-3-butyn-2-ol under copper catalyst conditions has been developed through a one-step one-pot sequence. This method provides a concise and efficient pathway to synthesize 1-monosubstituted-1, 2, 3-triazole derivatives in good to excellent yields.
- Liu, Yaowen,Han, Chunmei,Ma, Xinyuan,Yang, Jianhua,Feng, Xuepu,Jiang, Yubo
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supporting information
p. 650 - 653
(2018/01/15)
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- HEPARAN SULFATE BIOSYNTHESIS INHIBITORS FOR THE TREATMENT OF DISEASES
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Described herein are compounds of Formula I, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or conditions in need of inhibition of heparan sulfate biosynthesis.
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Paragraph 000186; 000501
(2016/05/02)
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- PYRROLO AND PYRAZOLOPYRIMIDINES AS UBIQUITIN-SPECIFIC PROTEASE 7 INHIBITORS
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The invention relates to inhibitors of USP7 inhibitors useful in the treatment of cancers, neurodegenerative diseases, immunological disorders, inflammatory disorders, cardiovascular diseases, ischemic diseases, viral infections and diseases, and bacterial infections and diseases, having the Formula: where m, n, X1, X2, R1-R5, R5′ and R6 are described herein.
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Paragraph 2111; 2112
(2016/08/03)
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- NOVEL COMPOUNDS
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The present invention relates to novel compounds and methods for the manufacture of inhibitors of deubiquitylating enzymes (DUBs). In particular, the invention relates to the inhibition of ubiquitin C-terminal hydrolase L1 (UCHL1). The invention further relates to the use of DUB inhibitors in the treatment of cancer and other indications. Compounds of the invention include compounds having the formula (I) or a pharmaceutically acceptable salt thereof, wherein R1 to R8 are as defined herein.
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Page/Page column 65
(2016/04/20)
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- Pd-catalyzed regioselective arylation on the C-5 position of N-aryl 1,2,3-triazoles
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We herein report a highly efficient method for the arylation at the C-5 position of N-aryl 1,2,3-triazoles via a direct palladium catalyzed arylation reaction. The optimal reaction conditions required a combination of Pd(OAc)2 and tris(o-tolyl)
- Yamajala, K. Durga Bhaskar,Patil, Mahendra,Banerjee, Shaibal
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supporting information
p. 3003 - 3011
(2015/03/30)
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- An organocatalytic azide-aldehyde [3+2] cycloaddition: High-yielding regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles
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An organocatalytic azide-aldehyde [3+2] cycloaddition (organo-click) reaction of a variety of enolizable aldehydes is reported. The organo-click reaction is characterized by a high rate and regioselectivity, mild reaction conditions, easily available subs
- Ramachary, Dhevalapally B.,Shashank, Adluri B.,Karthik
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supporting information
p. 10420 - 10424
(2016/02/18)
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- Synthesis of thermally stable energetic 1,2,3-triazole derivatives
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Various thermally stable energetic polynitro-aryl-1,2,3-triazoles have been synthesized through Cu-catalyzed [3+2] cycloaddition reactions between their corresponding azides and alkynes, followed by nitration. These compounds were characterized by analyti
- Kumar, A. Sudheer,Ghule, Vikas D.,Subrahmanyam,Sahoo, Akhila K.
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supporting information
p. 509 - 518
(2013/02/23)
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- Green synthesis of 1-monosubstituted 1,2,3-triazoles via 'click chemistry' in water
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The copper-catalyzed click reaction of organic azides with acetylene gas to give 1,2,3-triazoles using water as solvent was studied. The best yields are obtained in the presence of 10 mol% of CuI and 20 mol% of Et3N. Several 1-substituted triaz
- Wu, Luyong,Yan, Bo,Yang, Guo,Chen, Yuxue
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p. 397 - 400
(2014/01/06)
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- HIV PROTEASE INHIBITORS
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Compounds of Formula I are disclosed: wherein A, R1, R2, R3, R4A, R4B, R5, R6 and R7 are defined herein. The compounds encompassed by Formula I include compounds which
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Page/Page column 33-34
(2013/05/21)
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- A novel approach to 1-monosubstituted 1,2,3-triazoles by a click cycloaddition/decarboxylation process
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The synthesis of 1-monosubstituted 1,2,3-triazoles was achieved using azides and propiolic acid by copper-catalyzed click cycloaddition/ decarboxylation, which was easily carried out in N,N-dimethylformamide at room temperature or 60 C with yields ranging
- Xu, Mei,Kuang, Chunxiang,Wang, Zhuo,Yang, Qing,Jiang, Yubo
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supporting information; experimental part
p. 223 - 228
(2011/03/18)
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- A combined experimental and theoretical study of the thermal cycloaddition of aryl azides with activated alkenes
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Reactions were performed from aryl azides on the one hand, and activated alkenes coming from β-dicarbonyl compounds or malonodinitrile on the other hand, either with recourse to conventional heating or to microwave activation, to afford 1-aryl-1H-1,2,3-tr
- Zeghada, Sarah,Bentabed-Ababsa, Ghenia,Derdour, Aicha,Abdelmounim, Safer,Domingo, Luis R.,Saez, Jose A.,Roisnel, Thierry,Nassar, Ekhlass,Mongin, Florence
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experimental part
p. 4295 - 4305
(2011/07/08)
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- The use of calcium carbide in the synthesis of 1-monosubstituted aryl 1,2,3-triazole via click chemistry
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The synthesis of 1-monosubstituted aryl 1,2,3-triazoles was achieved using calcium, carbide as a source of acetylene. The copper-catalyzed 1,3-dipolar cycloaddition reactions were carried out without nitrogen protection and in a MeCN - H2O mixt
- Jiang, Yubo,Kuang, Chunxiang,Yang, Qing
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experimental part
p. 3163 - 3166
(2010/03/04)
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- A convenient synthesis of 1-substituted 1,2,3-triazoles via CuI/Et 3N catalyzed 'click chemistry' from azides and acetylene gas
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Copper(I)-catalyzed 'click chemistry' using acetylene gas was successfully explored under mild conditions. 1-Substituted-1,2,3-triazoles were conveniently synthesized from the corresponding aromatic and aliphatic azides. Georg Thieme Verlag Stuttgart.
- Wu, Lu-Yong,Xie, Yong-Xin,Chen, Zi-Sheng,Niu, Yan-Ning,Liang, Yong-Min
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experimental part
p. 1453 - 1456
(2009/10/23)
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- Monosubstituted 1,2,3-triazoles from two-step one-pot deprotection/click additions of trimethylsilylacetylene
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Two-step one-pot reaction conditions have been developed for synthesizing 1-substituted-1,2,3-triazoles. This transformation involves the base-catalyzed deprotection of trimethylsilylacetylene followed by Cu-catalyzed Huisgen 1,3-dipolar cycloaddition under aqueous reaction conditions. Utilization of potassium carbonate as the base and methanol as the alcoholic aqueous co-solvent resulted in optimal yields of the desired products. The reaction conditions were found to be successful for both alkyl and aryl azide reactants, including analogs with electron-donating and electron-withdrawing functionality. This procedure stands as a simple and regioselective means by which to prepare 1-substituted-1,2,3-triazole compounds directly from azide precursors.
- Fletcher, James T.,Walz, Sara E.,Keeney, Matthew E.
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scheme or table
p. 7030 - 7032
(2009/04/07)
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- 1-(2-Naphthyl)-1H-pyrazole-5-carboxylamides as potent factor Xa inhibitors. Part 2: A survey of P4 motifs
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A variety of P4 motifs have been examined to increase the binding affinity and in vitro anticoagulant potency of our biphenyl 1-(2-naphthyl)-1H-pyrazole-5- carboxylamide-based fXa inhibitors. Highly potent 2-naphthyl-P1 fXa inhibitors (Ki≤2 nM) with improved in vitro anticoagulant activity (2×TG≤1 μM) and respectable pharmacokinetic properties have been discovered.
- Jia, Zhaozhong J.,Wu, Yanhong,Huang, Wenrong,Zhang, Penglie,Clizbe, Lane A.,Goldman, Erick A.,Sinha, Uma,Arfsten, Ann E.,Edwards, Susan T.,Alphonso, Merlyn,Hutchaleelaha, Athiwat,Scarborough, Robert M.,Zhu, Bing-Yan
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p. 1221 - 1227
(2007/10/03)
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- Optically active antifungal azoles. XI. An alternative synthetic route for 1-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl )propyl]-3-[4-(1H-1-tetrazolyl)phenyl]-2-imidazolidinone (TAK-456) and its analog
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New routes for the synthesis of the optically active antifungal triazoles 1-[(1R,2R)-2-(2,4-difluorophenyl)-2-Hydroxy-1-Methyl-3-(1H-1,2,4-triazol-1-Yl )propyl]-3-[4-(1H-1-tetrazolyl)phenyl]-2-imidazolidinone (1b) and the 3-[4-(1H-1,2,3-triazol-1-Yl)phenyl]-2-imidazolidinone analog (1a) that possess an imidazolidine nucleus were established. The key synthetic intermediates, (2R,3R)-3-(2,2-diethoxyethyl)amino-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol -1-Yl)-2-butanol (8) and (2R,3R)-2-(2,4-difluorophenyl)-3-(2-hydroxyethyl)amino-1-(1H-1,2,4-triazol-1- yl)-2-butanol (14), were prepared by the ring-Opening reaction of the oxirane (2) with the corresponding 2-Substituted ethylamines. The acetal (8) was converted to the imidazolidinones (1a, b) by condensation with the carbamates (10a, b) followed by treatment with hydrochloric acid and subsequent catalytic hydrogenation. The candidate selected for the clinical trials, 1b (TAK-456), was alternatively prepared from the hydroxyethylamino intermediate (14) via two reaction steps: condensation with the carbamate (10b) to the urea (15) and subsequent cyclization to the imidazolidinones. This newly developed synthetic route could be applied to a large scale preparation of 1b.
- Ichikawa, Takashi,Kitazaki, Tomoyuki,Matsushita, Yoshihiro,Hosono, Hiroshi,Yamada, Masami,Mizuno, Masahiro,Itoh, Katsumi
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p. 1947 - 1953
(2007/10/03)
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- Optically active antifungal azoles. X. Synthesis and antifungal activity of N-[4-(azolyl)phenyl]- and N-[4-(azolylmethyl)phenyl]-N′-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy -1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-azolones
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New optically active antifungal azoles, N-[4-(azolyl)phenyl]- and N-[4-(azolylmethyl)phenyl]-N′-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy -1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]azolones (1, 2, 3), were prepared in a stereocontrolled manner. Compounds 1
- Kitazaki, Tomoyuki,Ichikawa, Takashi,Tasaka, Akihiro,Hosono, Hiroshi,Matsushita, Yoshihiro,Hayashi, Ryogo,Okonogi, Kenji,Itoh, Katsumi
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p. 1935 - 1946
(2007/10/03)
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- Azole compounds, their production and use
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PCT No. PCT/JP96/00325 Sec. 371 Date Oct. 17, 1996 Sec. 102(e) Date Oct. 17, 1996 PCT Filed Feb. 15, 1996 PCT Pub. No. WO96/25410 PCT Pub. Date Aug. 20, 1996The present invention provides an azole compound represented by the formula (I): wherein Ar is an
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- Regiospecific fragmentation of benzene derivatives: Synthetic and analytical applications
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The cycloadducts formed from arenes and tetrachloro- and tetrafluorobenzyne have been shown to undergo specific addition-fragmentation reactions. These sequences are both simple syntheses of arenes with unusual substitution patterns and a convenient alternative to the other methods currently available for assaying the isotopic distribution in [14C]-labelled benzene derivatives.
- Hales, Neil J.,Heaney, Harry,Hollinshead, John H.,Ley, Steven V.
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p. 7755 - 7776
(2007/10/02)
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- Intermolecular Thermal Reaction of Arylnitrenes with Furans
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4-Methoxy-, 4-chloro-, and 4-nitro-phenylnitrenes have been thermally generated by decomposition of the corresponding aryl azides in the presence of furan and a series of 2-substituted and 2,5-disubstituted furans. 4-Nitrophenylnitrene has been shown to be capable of undergoing electrophilic addition to the furan ring both at the α- and β-position, whereas only evidence of α-attack has been provided by 4-chlorophenylnitrene.On the other hand, no evidence of electrophilic attack has been obtained with 4-methoxyphenylnitrene, which affords only products ascribable to the triplet nitrene.The formation of a number of products ultimately resulting from nitrene attack at the α-position of the furan ring followed by a ring-opening process and the general occurrence of 1-(4-nitrophenyl)- and 1-(4-chlorophenyl)-1,2,3-triazole from thermolysis of 4-nitro- or 4-chloro-phenyl azide in the presence of the furans examined is discussed.
- Benati, Luisa,Montevecchi, Pier Carlo,Toselli, Maurizio,Spagnolo, Piero
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p. 1859 - 1864
(2007/10/02)
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- 1,3-DIPOLAR CYCLOADDITIONS TO 2,3-DIMETHOXYCARBONYL-7-OXABICYCLO-2,5-HEPTADIENE, 1,4-EPOXY-1,4-DIHYDRONAPHTHALENE, AND exo-endo-1,6-DIMETHOXYCARBONYL-11,12-DIOXATETRACYCLO2,5,17,10>-3,8-DODECADIENE
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The paper deals with site-selectivity of l,3-dipolar cycloadditions of ethyl azidoformate, azidoacetate, and diazo acetate to 2,3-dimethoxycarbonyl-7-oxabicyclo-2,5-heptadiene.The exo-endo stereoselectivity has been studied of the reactions of 1,4-
- Fisera, L'ubor,Pavlovic, Dusan
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p. 1990 - 2000
(2007/10/02)
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- SITE-SELECTIVITY OF 1,3-DIPOLAR CYCLOADDITIONS TO 2,3-DIMETHOXYCARBONYL-7-OXABICYCLO-HEPTADIENE
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Site-selectivity of dipolar cycloaddition to the title compound was studied.Azomethine X afforded a 1:1 cycloadduct XI at the deactivated double bond at room temperature;upon thermolysis at 110 degC it afforded the acetylated enamine XIII, wich was formed wia a direct cycloaddition at the mentioned temperature.The cycloaddition course was investigated in various solvents;the enamine XIV formed by solvolysis of XIII was the final products in methanol.Cycloaddition of title compound to azides, benzoylnitrile N-oxide and C-acetyl-N-phenylnitrilimine furnished the product of cycloreversion instead of the not isolable 1:1 cycloadducts.5-Azido-2-furancarbaldehyde and 4-nitrophenylazide yielded cycloaddition products to both multiple bonds in an approximately 1:1 ratio: HN3, tosylazide,benzoylnitrile N-oxide and C-acetyl-N-phenylnitrilimine gave the addition products to the deactivated double bond.The solvent-effect of site-selectivity of 1,3-dipolarcycloaddition was inwestigated and the title compound was found to be an exellent synthetic equivalent for acetylene and dimethyl butinedioate.
- Fisera, Lubor,Povazanec, Frantisek,Zalupsky, Peter,Kovac, Jaroslav,Pavlovic, Dusan
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p. 3144 - 3153
(2007/10/02)
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- SITE SELECTIVITY IN THE REACTIONS OF 1,3-DIPOLES WITH NORBORNADIENE DERIVATIVES
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The cycloadditions of arylazides, benzonitrile oxides and diphenylnitrile imine to norbornadiene derivatives 1a-c showed varying degree of site- and stereo-selectivity.With dipolarophile 1a arylazides and benzonitrile oxides attack, preferentially, the electron-poor tetrasubstituted double bond, while in the case of 1b and 1c is the substituted double bond which enters the cycloaddition.By contrast, 2-diazopropane and C-phenyl-N-methylnitrone react with the sole tetrasubstituted double bond of 1a-c in stereo- and site-specific cycloadditions.The quantitative evaluation of the two possible reaction paths was performed by glc analysis.The compounds detected were those arising from Diels-Alder cycloreversions of the thermally labile intermediate adducts 2 and 3 (Scheme 1).The results were rationalized on the basis of a qualitative perturbation treatment which considers frontier orbital interactions only.
- Cristina, D.,Amici, M. De,Micheli, C. De,Gandolfi, R.
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p. 1349 - 1357
(2007/10/02)
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- v-Triazolines. Part 12. Synthesis of 5-Amino-1-aryl-4-methylene-4,5-dihydro-v-triazoles
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A series of 5-amino-4-aminomethyl-1-aryl-4,5-dihydro-v-triazoles was synthesized.On reaction with methyl iodide or methyl trifluoromethanesulphonate the corresponding 4-(quaternary)ammoniomethyl salts were obtained.These derivatives, on treatment with sev
- Croce, Piero Dalla,Pocar, Donato,Stradi, Riccardo,Trimarco, Pasqualina
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p. 141 - 145
(2007/10/02)
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