- Ammonium Arylspiroborate Compounds: Synthesis, Crystal Structure, Fluorescence Properties, and Antibacterial Activity
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A series of R-substituted ammonium arylspiroborate compounds (R = CH3, H, F, Cl, Br) have been synthesized via a facile one-pot method. The structures of these new kinds of boron compounds were characterized by IR, NMR spectra, elemental analys
- Wang, Qiaoyun,Zhou, Hong
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- Azole-carbodithioate hybrids as vaginal anti-Candida contraceptive agents: Design, synthesis and docking studies
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Azole and carbodithioate hybrids were synthesized as alkyl 1H-azole-1-carbodithioates (7-27) and evaluated for spermicidal/microbicidal activities against human sperm, Trichomonas vaginalis and Candida species. Seventeen compounds (7-14, 16-18 and 20-25)
- Kumar, Lalit,Lal, Nand,Kumar, Vikash,Sarswat, Amit,Jangir, Santosh,Bala, Veenu,Kumar, Lokesh,Kushwaha, Bhavana,Pandey, Atindra K.,Siddiqi, Mohammad I.,Shukla, Praveen K.,Maikhuri, Jagdamba P.,Gupta, Gopal,Sharma, Vishnu L.
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- The Mitsunobu reaction: An alternative synthesis of 1-(primary alkyl)benzotriazoles
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1-(Primary alkyl)benzotriazoles are obtained in convenient yields by treating the corresponding alcohol with triphenylphosphine, N-bromosuccinimide and benzotriazole. Under these conditions, the alcohols gave exclusively the corresponding 1-alkyl-benzotriazoles. Allyl and propargyl alcohols also reacted regiospecifically in a typical S(N)2 manner, and no products derived from prototropic rearrangement were found.
- Katritzky, Alan R.,Oniciu, Daniela C.,Ghiviriga, Ion
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- 1H,6H-Triazolo[4,5-e]benzotriazole-3-oxides and 5,5′-(Z)-diazene-1,2-diylbis(2-methyl-2H-1,2,3-benzotriazole) derived from chloronitrobenzotriazoles and hydrazine
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Nitration of 5-chlorobenzotriazole (1) and its N1-methyl derivatives (2 and 3) produced 5-chloro-4-nitrobenzotriazole (5), 5-chloro-1-methyl-4-nitrobenzotriazole (6) and 6-chloro-1-methyl-7-nitrobenzotriazole (7) respectively. Nitration of 5-chloro-2-methylbenzotriazole (4) gave either 5-chloro-2-methyl-4-nitrobenzotriazole (8) or 5-chloro-2-methyl-4,6-dinitrobenzotriazole (9). Introduction of the nitro group activated chlorine atom that underwent nucleophilic displacement by hydrazine to give rise to a new tricyclic system 1H,6H-triazolo[4,5-e]benzotriazole-3-oxide compounds (10 and 11) in the case of 5 and 6. From 9 no linear or angular tricyclic triazolobenzotriazole was obtained but instead the 5,5′-(Z)-diazene-1,2-diylbis(2-methyl-2H-1,2,3-benzotriazole) (18).{A figure is presented}.
- Carta, Antonio,Piras, Sandra,Boatto, Gianpiero,Paglietti, Giuseppe
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- Reaction of N-vinylindazolium and N-vinylbenzotriazolium salts with nucleophiles
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Reaction of N-vinylindazolium tetrafluoroborates with aqueous potassium carbonate or sodium borohydride affords 2,3-dihydroquinazolines which evolve to 1,2,3,4-tetrahydroquinazolines by intra or intermolecular nucleophilic attack. The X-ray structure of o
- Elguero, Jose,Gutierrez-Puebla, Enrique,Monge, Angeles,Parco, Carmen,Ramos, Mar
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- A NEW SIMPLE PROCEDURE FOR ALKYLATION OF NITROGEN HETEROCYCLES USING DIALKYL OXALATES AND ALKOXIDES.
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A variety of nitrogen heterocycles are N-alkylated in high yields with dialkyl oxalates and potassium alkoxides in refluxing dimethylformamide.
- Bergman, Jan,Sand, Peter
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- Mechanistic study of nucleophilic fluorination for the synthesis of fluorine-18 labeled fluoroform with high molar activity fromN-difluoromethyltriazolium triflate
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The synthesis of fluorine-18 labeled fluoroform with high molar activity has grown in importance for the development of fluorine-18 labeled aryl-CF3radiopharmaceuticals that are useful as diagnostic radiotracers for the powerful technique of positron emission tomography (PET). We designed a strategy of synthesizing fluorine-18 labeled fluoroform fromN1-difluoromethyl-N3-methyltriazolium triflate (1)viaSN2 fluorination without stable fluorine isotope scrambling. Fluoroform was generated at rt in 10 min by fluorination of the triazolium precursor with TBAF (6 equiv.). We propose three routes (a), (b), and (c) for this fluorination. Quantum chemical calculations have been carried out to elucidate the mechanism of experimentally observed nucleophilic attack of fluoride at difluoromethyl groupviaroute (a), notN3-methylviaroute (b).1H and19F NMR studies using deuterium source have been performed to examine the competition between SN2 fluorination (route (a)) and the formation of difluorocarbene (route (c)). The observed superiority of SN2 pathway to formation of difluorocarbene in the reaction of the precursor using CsF in (CD3CN/(CD3)3COD (17.8?:?1)) gives the possibility of preparing the fluorine-18 labeled fluoroform in high molar activity.
- Chai, Jin Young,Cha, Hyojin,Lee, Sung-Sik,Oh, Young-Ho,Lee, Sungyul,Chi, Dae Yoon
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p. 6099 - 6106
(2021/02/12)
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- Bu4NI-Catalyzed, Radical-Induced Regioselective N-Alkylations and Arylations of Tetrazoles Using Organic Peroxides/Peresters
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Bu4NI-catalyzed regioselective N2-methylation, N2-Alkylation, and N2-Arylation of tetrazoles have been achieved using tert-butyl hydroperoxide (TBHP) as the methyl source, alkyl diacyl peroxides as the primary alkyl source, alkyl peresters as the secondary and tertiary alkyl sources, and aryl diacyl peroxides as the arylating source. These reactions proceed without pre-functionalization of tetrazole and in the absence of any metal catalysts. Here, peroxides serve the dual role of oxidants as well as alkylating or arylating agents. Based on DFT calculations, it was found that spin density, transition-state barriers (kinetic control), and thermodynamic stability of the products (thermodynamic control) play essential roles in the observed regioselectivity during N-Alkylation. This radical-mediated process is amenable to a broad range of substrates and provides products in moderate to good yields.
- Ghosh, Subhendu,Mir, Bilal Ahmad,Patel, Bhisma K.,Rajamanickam, Suresh,Sah, Chitranjan,Sethi, Garima,Venkataramani, Sugumar,Yadav, Vinita
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p. 2118 - 2141
(2020/03/13)
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- Alkylation method for nitrogen-hydrogen containing compounds and application thereof
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The invention discloses an alkylation method for nitrogen-hydrogen containing compounds and an application thereof, belonging to the technical field of synthesis of organic compounds. The invention provides a series of methods for a nitrogen alkylation reaction of N-H containing heterocyclic compounds (II) with N,N-dimethylformamide dialkyl acetal as an alkyl source under the condition of no participation of metals, and a product with a hydrogen atom on a nitrogen atom substituted by R1 is obtained. The method provided by the invention has the advantages of highly-efficient reaction, high yield, simple treatment after the reaction, simple and convenient operation, mild reaction conditions, no participation of the metals, high tolerance of functional groups of a reaction substrate, wide range and easy preparation of the substrate, high reaction efficiency after amplification of the reaction, and applicability to large-scale industrial production.
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Paragraph 0045-0047
(2018/10/04)
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- Derisking the Cu-Mediated 18F-Fluorination of Heterocyclic Positron Emission Tomography Radioligands
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Molecules labeled with fluorine-18 (18F) are used in positron emission tomography to visualize, characterize and measure biological processes in the body. Despite recent advances in the incorporation of 18F onto arenes, the development of general and efficient approaches to label radioligands necessary for drug discovery programs remains a significant task. This full account describes a derisking approach toward the radiosynthesis of heterocyclic positron emission tomography (PET) radioligands using the copper-mediated 18F-fluorination of aryl boron reagents with 18F-fluoride as a model reaction. This approach is based on a study examining how the presence of heterocycles commonly used in drug development affects the efficiency of 18F-fluorination for a representative aryl boron reagent, and on the labeling of more than 50 (hetero)aryl boronic esters. This set of data allows for the application of this derisking strategy to the successful radiosynthesis of seven structurally complex pharmaceutically relevant heterocycle-containing molecules.
- Taylor, Nicholas J.,Emer, Enrico,Preshlock, Sean,Schedler, Michael,Tredwell, Matthew,Verhoog, Stefan,Mercier, Joel,Genicot, Christophe,Gouverneur, Véronique
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supporting information
p. 8267 - 8276
(2017/06/27)
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- Sodium hydrogen exchanger inhibitory activity of benzotriazole derivatives
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Series of benzotriazole derivatives were synthesized and evaluated for their Sodium hydrogen exchanger-1 inhibitory potential. All compounds inhibit Sodium hydrogen exchanger-1 in the in-vitro platelet swelling assay. This is perhaps the first report of NHE-1 inhibitory activity of benzotriazole. The 1-alkyl benzotriazole derivatives were found to be more active than the 2-alkyl isomers. The activity increases with increase in chain length of alkyl moiety. Potency increased from that of benzotriazole (IC50= 192.68 μM) to heptyl derivative (compound 13; IC50= 59.23 μM). Introduction of electronegative oxygen atom further increased potency as shown by the benzoyl (compound 16, IC50= 51.57 μM) and sulfonyl groups (compound 17, IC50= 50.89 μM; compound 18, IC50= 49.95 μM).
- Singh, Dhandeep,Silakari, Om
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p. 183 - 189
(2016/10/25)
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- Potassium Iodide/tert-Butyl Hydroperoxide-Mediated Oxidative Annulation for the Selective Synthesis of N-Substituted 1,2,3-Benzotriazine-4(3H)-ones Using Nitromethane as the Nitrogen Synthon
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A novel and efficient oxidative annulation of 2-aminobenzamides with nitromethane has been developed for the chemoselective synthesis of N-substituted 1,2,3-benzotriazine-4(3H)-ones in moderate to excellent yields under transition metal-free conditions. T
- Yan, Yizhe,Niu, Bin,Xu, Kun,Yu, Jianhua,Zhi, Huanhuan,Liu, Yanqi
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supporting information
p. 212 - 217
(2016/02/14)
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- ULTRAVIOLET RADIATION ABSORBING POLYETHERS
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A polymer composition comprising a linear ultraviolet radiation absorbing polyether that comprises a chemically bound UV-chromophore.
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Page/Page column
(2014/02/15)
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- N-methylation of NH-containing heterocycles with dimethyl carbonate catalyzed by TMEDA
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A practical method for N-methylation of NH-containing heterocycles using an environmentally safe and less toxic methylating reagent, dimethyl carbonate, has been developed. N,N,N',N'-tetramethylethylenediamine (TMEDA), an extremely active organocatalyst for the methylation of imides, indoles, benzimidazoles, and piperazines in conjunction with dimethyl carbonate, can lead to N-methylation products with high conversion. The reaction sequence consists of competing alkylation and acylation pathways and involves TMEDA as a nucleophilic catalyst. A possible reaction mechanism is discussed based on the reaction results.
- Zhao, Sheng-Yin,Zhang, Hai-Quan,Zhang, Deng-Qing,Shao, Zhi-Yu
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experimental part
p. 128 - 135
(2011/11/01)
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- Convenient and stereoselective synthesis of symmetrical (E)-stilbenes via homocoupling of 1,3-dibenzylbenzotriazolium bromides
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Using NaH as the base and DMSO as the solvent, a series of symmetric (E)-stilbenes were prepared in good yields via the -homocoupling of 1,3-dibenzylbenzotriazolium bromides at room temperature. Georg Thieme Verlag Stuttgart · New York.
- Xiao, Xiaohui,Lin, Daqin,Tong, Shuitian,Luo, Hong,He, Yinfeng,Mo, Hailan
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supporting information; experimental part
p. 1731 - 1734
(2011/09/16)
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- Organic reactions in ionic liquids: An efficient method for the N-alkylation of benzotriazole
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The N-alkylation of benzotriazole with alkyl halides proceeds efficiently in the presence of potassium hydroxide in ionic liquid 1-butyl-3- methylimidazolium tetrafluoroborate ([Bmim][BF4]).
- Le, Zhang-Gao,Chen, Zhen-Chu,Hu, Yi,Zheng, Qin-Guo
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p. 344 - 346
(2007/10/03)
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- Synthesis of intra annularly linked benzotriazolophane
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Reduction of 1,3-dialkyl benzotriazolium salts was carried out using NaH/THF. The methodology was applied for the synthesis of benzotriazolophane 2, which was intra annularly linked by p-xylenyl dibromide to give novel cyclophane 6 and reduction of benzot
- Rajakumar, Perumal,Murali, Venghatragavan,Kalaivasan, Natarajan
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p. 1685 - 1690
(2007/10/03)
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- Synthesis and crystal structure of 1,3-dimethyl benzotriazolium trifluoromethane sulfonate
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The isolation of stable carbenes of the Arduengo (1a) and Wanzlick (2a) type has prompted us to look for stable nitrenium ions of the related structural type 1,3-dimethyl benzotriazolium trifluoromethane sulfonate (3+). The title compound was i
- Rangappa,Mallesha,Kumar,Lokanath,Sridhar,Prasad
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p. 291 - 298
(2007/10/03)
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- Photochemistry of 1H-benzotriazole in aqueous solution: A photolatent base
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Flash photolysis of 1H-benzotriazole (1) has shown that N-N bond fission occurs within a few picoseconds of excitation (248 nm) giving 6-diazo-2,4-cyclohexadien-1-imine (2), λmax = 430 nm. Fluorescence and intersystem crossing do not compete measurably, and photodenitrogenation is a minor side reaction (9 s-1 in aprotic solvents, and 3.2 x 107 s-1 in aqueous solution. DFT calculations gave Δ2→1G? = 3.7 and Δ2→1G° = -28.0 kcal mol-1 for the activation and reaction free energies, respectively, Imine 2 is a moderately strong base, pKa = 12.7, that is protonated by water yielding 2-aminophenyl diazonium ion (2+), λmax = 405 nm. The rate constant for cyclization of the cation, 2+ → 1 + H+, is k = 3 s-1. The reversible photoreaction of 1 may be used to induce an upward pH jump in unbuffered water, or as a kinetic pH-indicator for the range of 6-12 in buffered solutions. An erroneous value for the acidity constant of protonated 1 is corrected to pATa(1+) = 0.42 ± 0.02 (I = 1.0 M). Several derivatives of 1 were also investigated.
- Wang, Hong,Burda, Clemens,Persy, Gaby,Wirz, Jakob
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p. 5849 - 5855
(2007/10/03)
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- Synthesis of triazolo[4,5-f]quinolines. An unusual case of displacement of nitro group in the reaction of 8-acetylamino-6-chloro-5-nitroquinoline with hydrazine and methylhydrazine
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Nitration of 1H-, 3-methyl- and 2-methyltriazolo[4,5-f]quinolines (6a-c) as a way to obtain the desired 4-aminotriazolo[4,5-f]quinolines (4) for a medicinal chemistry project was successful only in the case of 6c. Attempted building up of the triazole ring starting from 8-acetylamino-6-chloro-5- nitroquinoline (8) with ammonia, hydrazine and methylhydrazine at 150 °C in ethanol failed. However, the results obtained from these reactions allowed us to observe that, during nucleophilic aromatic substitution of chlorine by these bases an unusual displacement of the nitro group by hydrogen occurred. Comparison of these results with those obtained using different substrates allowed us to evaluate the influence of both para-acetylamino group and pyridine ring in this type of nucleophilic aromatic substitution.
- Sanna, Paolo,Carta, Antonio,Paglietti, Giuseppe
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p. 693 - 702
(2007/10/03)
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- Reactions of chloride salts of 7-amino-9-ethylguanine and 1-amino-3- methylbenzimidazoles with lead(IV) acetate: Formation of 8-aza-9-ethylguanine and 1-methyl-1H-benzotriazoles
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Reaction of 7-amino-9-ethylguaninium chloride with lead(IV) acetate (LTA) in MeOH yielded 8-aza-9-ethylguanine. Similarly, the reaction of 1- amino-3-methylbenzimidazolium chloride or its substituted derivatives (6- methyl,5,6-dimethyl and 5-nitro) with LTA gave the corresponding 1-methyl- 1H-benzotriazole (or 1-methyl-2-azabenzimidazole) derivatives along with N- methylformanilide derivatives.
- Kaiya, Toyo,Aoyama, Shinsuke,Kohda, Kohfuku
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p. 961 - 964
(2007/10/03)
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- Observation of a single-pot aromatic reductive denitration
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4,N,N-Trimethyl-3-nitrobenzenamine gave reductive denitration products (ca. 28%) upon treatment with n-butyl nitrite in the presence of catalytic amounts of ammonium chloride and water in an unprecedented one-reagent single-pot process. The three isomeric N,N-dimethylnitrobenzenamines showed the same behaviour to a much lesser extent; the ortho isomer was partially (7%) transformed into 1-methylbenzotriazole.
- Giumanini, Angelo G.,Verardo, Giancarlo
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p. 469 - 473
(2007/10/03)
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- Condensation of benzotriazole with O-alkyl P-(dichloromethyl) chlorophosphonate: Some unusual observations
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The condensation of benzotriazole with O-alkyl P-(dichloromethyl) chlorophosphonate give corresponding 1-alkylbenzotriazole rather than desired N-(benzotriazol-1-yl) P-(dichloromethyl) O-alkyl phosphonate.
- Singh, Neera,Dureja, Prem
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p. 700 - 702
(2007/10/03)
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- Oxidative Alkylation of Azoles. IV. Reaction of N-Halo- and N-Nitrobenzotriazoles with Methyl Iodide
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Reactions of N-chloro-, N-bromo-, N-iodo-, and N-nitrobenzotriazoles with methyl iodide yield products of mono- and dialkylation at the heteroatoms and also unsubstituted benzotriazole.The reaction of N-chlorobenzotriazole with methyl iodide yields also N
- Kurenkov, A. A.,Pevzner, M. S.
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p. 1122 - 1124
(2007/10/03)
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- SELECTIVE ALKYLATIONS OF 1,2,4-TRIAZOLE AND BENZOTRIAZOLE IN THE ABSENCE OF SOLVENT
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Alkylation of 1,2,4-triazole and benzotriazole has been performed either in basic media under solvent free phase transfer catalysis conditions or in the absence of base by conventional and microwave heating.Several parameters affecting the selectivity have been studied.In the case of triazole alkylation, microwave irradiation produces specific (non thermal) effects both on reactivity and selectivity.
- Abenhaim, David,Diez-Barra, Enrique,Hoz, Antonio de la,Loupy, Andre,Sanchez-Migallon, Ana
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p. 793 - 802
(2007/10/02)
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- A Novel Selective Route to 1-Substituted Benzotriazoles via Lithiation of Simple 1-Alkylbenzotriazoles
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1-Methylbenzotriazole (2a) is lithiated readily with butyllithium or LDA at the methyl group to 4 and the subsequent reaction with various electrophiles provides 1-substituted benzotriazoles 5.Other 1-(n-alkyl)benzotriazoles 2 also undergo lithiation with LDA, the carbanions can be trapped with alkyl halides giving benzotriazoles 6 bearing secondary alkyl groups on the N-1 atom.On standing in the absence of electrophiles, all the lithium derivatives decompose to afford complex mixtures. - Key Words: Benzotriazoles, 1-alkyl / Lithiation / Haloalkanes
- Katritzky, Alan R.,Wu, Jing,Kuzmierkiewicz, Wojciech,Rachwal, Stanislaw
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- Novel Conversions of Benzotriazol-1-ylmethyl Derivatives
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New (benzotriazol-1-yl)methyl derivatives of type BtCH2X (X = Br, I, ONO2) have been investigated.Ethyl (benzotriazol-1-yl)acetate (BtCH2CO2Et) is converted by treatment with butyl nitrite into the oximes BtCH:NOH of which the E isomer is stable but the Z
- Katritzky, Alan R.,Wu, Jing,Wrobel, Leszek,Rachwal, Stanislaw,Steel, Peter J.
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p. 167 - 175
(2007/10/02)
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- STUDIES ON THE THERMAL DECARBOXYLATION OF 1-ALKOXYCARBONYLBENZOTRIAZOLES
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1-Alkoxycarbonylbenzotriazoles on thermolysis lose carbon dioxide; the decarboxylation is accompanied by the formation of a mixture of 1- and 2-alkylbenzotriazoles, with the N-1 isomer predominating over the N-2 isomer in all cases.A cross-over experiment
- Katritzky, Alan R.,Zhang, Gui-Fen,Fan, Wei-Qiang,Wu, Jing,Pernak, Juliusz
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p. 567 - 573
(2007/10/02)
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- N-SULFONYLBENZOTRIAZOLES. PART 2. REACTIONS OF 1,1'-SULFONYLDIBENZOTRIAZOLE AND 1-BENZENESULFONYL-1,2,4-TRIAZOLE WITH ALCOHOLS; A NEW APPROACH TO N-ALKYLBENZOTRIAZOLES AND N-ALKYL-1,2,4-TRIAZOLES
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1,1'-Sulfonyldibenzotriazole (3) reacts with sodium alkoxides to give N-alkylbenzotriazoles.With alkanols, benzotriazolium alkyl sulfates are produced. 1-Benzenesulfonyl-1,2,4-triazole with sodium salts of alcohols gives 1-alkyl-1,2,4-triazoles.The mechanisms of these reactions are discussed.
- Katritzky, Alan R.,Zhang, Gui-Fen,Pernak, Juliuzs,Fan, Wei-Qiang
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p. 1253 - 1262
(2007/10/02)
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- An improved method for the N-alkylation of benzotriazole and 1,2,4-triazole
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The N-alkylation of benzotriazole and 1,2,4-triazole with alkyl halides proceeds efficiently in the presence of sodium hydroxide in N,N-dimethylformamide.
- Katritzky, Alan R.,Kuzmierkiewiecz, Wojciech,Greenhill, John V.
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p. 369 - 373
(2007/10/02)
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- Alkylation with Oxalic Esters. Scope and Mechanism.
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Alkyl oxalates are well suited for use as standard synthetic reagents in N-, O-, or S-alkylations and often display an interesting regioselectivity.The mechanism seems to be a direct alkylation of the substrate anion.
- Bergman, Jan,Norrby, Per-Ola,Sand, Peter
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p. 6113 - 6124
(2007/10/02)
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- Reactions of 1-(α-Alkoxyalkyl)- and 1-(α-(Aryloxy)alkyl)benzotriazoles with the Grignard Reagents. A New and Versatile Method for the Preparation of Ethers
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1-(α-Alkoxyalkyl)benzotriazoles deriving from aldehydes (other than formaldehyde), or from ketones, react with Grignard reagents at 110 deg C to provide a high-yielding, general synthesis of dialkyl and aryl ethers.Under similar conditions, 1-(alkoxymethyl)- and 1-((aryloxy)methyl)benzotriazoles give, by a different cleavage pattern of the N-C-O grouping, 1-alkylbenzotriazoles and N,N'-dialkyl-o-phenylenediamines.The 1-(α-alkoxyalkyl)benzotriazoles are easily prepared: (a) by condensation of benzotriazole, an aldehyde, and an alcohol under water-removing conditions; (b) by condensation of a 1-(α-chloroalkyl)benzotriazole with a sodium or potassium alkoxide or aryloxide; and (c) by condensatioon of an acetal or a ketal with benzotriazole.All the 1-(α-alkoxyalkyl)benzotriazoles and dialkyl or alkyl aryl ethers obtained were fully characterized by their 1H and 13C NMR spectra.
- Katritzky, Alan R.,Rachwal, Stanislaw,Rachwal, Bogumila
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p. 6022 - 6029
(2007/10/02)
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- Benzotriazol-1-ylmethylammonium Salts Synthesis and Reactivity
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Benzotriazol-1-ylmethylamines on treatment with alkylating agents afford benzotriazol-1-ylmethylammonium salts, also available from reactions of chloromethylbenzotriazole with tertiary amines.In deuterated solvents under basic conditions the methylene protons of these salts exchange with deuterium.At elevated temperatures, an alkyl group substituent migrated from the ammonium center to the benzotriazolyl N-3.Reactions of the salts with Grignard reagents afforded various products arising from substitution of the ammonium moiety and/or from attack on the benzotriazolyl N-3 or on the benzenoid ring.
- Katritzky, Alan R.,Hughes, Craig V.,Rachwal, Stanislaw
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p. 1579 - 1588
(2007/10/02)
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- The Chemistry of N-Substituted Benzotriazoles. Part 1. 1-(Chloromethyl)-benzotriazole
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The N-chloromethyl group of 1-(chloromethyl)benzotriazole undergoes nucleophilic substitution by carbon, nitrogen, phosphorus, oxygen, and sulphur nucleophiles. α-Lithiation was achieved in high yield in 1-phenylthiomethyl-, 1-phenylsulphinylmethyl-, and 1-(phenylsulphonylmethyl)benzotriazoles and the lithio derivatives reacted with a variety of electrophiles.New benzotriazolium salts were prepared by quaternization of the N-3 nitrogen with methyl iodide.
- Katritzky, Alan R.,Rachwal, Stanislaw,Caster, Kenneth C.,Mahni, Fatma,Law, Kam Wah,Rubio, Olga
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p. 781 - 790
(2007/10/02)
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- Methylathion of Heterocyclic Compounds Containing NH, SH and/or OH Groups by Means of N,N-Dimethylformamide Dimethyl Acetal
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Methylations of heterocyclic systems, such as benzimidazole, naphthimidazole, imidazopyridine, purine, pyridine, pyrimidine, pyridazine and s-triazolopyridazine, which bore SH, NH and/or OH groups, were carried out with dimethylformamide dimethyl acetal to give the corresponding S-, N- and/or O-methyl derivatives in high yields.Selective methylation of some compounds containing both SH and NH groups took place to give first the S-methyl and subsequently the S,N-dimethyl derivatives.No side reactions, such as C-methylation, were observed.
- Stanovnik, Branko,Tisler, Miha,Hribar, Alenka,Barlin, Gordon B.,Brown, Desmond J.
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p. 1729 - 1738
(2007/10/02)
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- Phase-Transfer Alkylation of Heterocycles in the Presence of 18-Crown-6 and Potassium tert-Butoxide
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It has been found that the N-alkylation of heterocyclic compounds bearing an acidic hydrogen atom attached to nitrogen can be accomplished in diethyl ether via a phase-transfer process in which 18-crown-6 is employed as the catalyst and potassium tert-butoxide is employed as the base.In this manner, pyrrole (1), indole (2), pyrazole (3), imidazole (4), benzimidazole (5), benzotriazole (6), carbazole (7), and methyl indole-3-acetate (8) can be successfully alkylated.The procedure is convenient and mild and generally gives rise to exclusive N-alkylation.
- Guida, Wayne C.,Mathre, David J.
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p. 3172 - 3176
(2007/10/02)
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