- Ruthenium(II) porphyrin-catalyzed amidation of aromatic heterocycles
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(Equation Presented) Ruthenium(II) porphyrin-catalyzed amidation of aromatic heterocycles with iminoiodanes under mild conditions (CH 2Cl2, 4 A molecular sieves, ultrasound, 40°C) was achieved in moderate to good yields (up to 84%) and conversions (up to 99%). Only the N,N-ditosylamidated product was obtained for reactions involving heteroarenes, where X = O, S, or NTs. N-Alkyl- and N-aryl-substituted pyrroles, on the other hand, were shown to give the 3,4-diaminated adduct.
- He, Ling,Chan, Philip Wai Hong,Tsui, Wai-Man,Yu, Wing-Yiu,Che, Chi-Ming
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- Utilization of caffeine carbon supported cobalt catalyst in the tandem synthesis of pyrroles from nitroarenes and alkenyl diols
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Employing bio-waste caffeine carbon-supported heterogeneous cobalt catalyst, synthesis of various substituted pyrrole derivatives is reported. In this methodology, pyrroles were synthesized through coupling between nitroarenes and alkenyl diols in a tandem manner. Among all the heterogeneous catalysts Co(OAc)2-CC-800 displayed the highest catalytic activity. Preparative scale synthesis of pyrroles and synthesis of anti-tubercular agent 5-(4-(1H-pyrrol-1-yl)phenyl)-1,3,4-oxadiazole-2-thiol revealed the practical applicability of this protocol. Several kinetic experiments and Hammett studies were conducted to understand the probable mechanism and electronic effects on this transformation.
- Balasubramaniam, Bhuvaneshwari,Dhara, Partha,Gupta, Raju K.,Kundu, Sabuj,Panja, Dibyajyoti,Sau, Anirban
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p. 244 - 254
(2021/09/07)
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- Solvent Free Synthesis of N-Substituted Pyrroles Catalyzed by Calcium Nitrate
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Moderated and mild way for synthesizing N-substituted pyrrole has been demonstrated herein. No solvents need to be used for this reaction, and instead, reactants themselves acted as a reaction medium. In fact, the reaction is carried out using catalytic amount of Ca(NO3)2.4H2O. The reaction conditions are selective and mild that helped to tolerate a wide variety of functional groups to give the desired products in good chemical yields.
- Wani, Rucha R.,Chaudhari, Hemchandra K.,Takale, Balaram S.
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supporting information
p. 1337 - 1340
(2019/02/05)
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- Copper-catalysed N-arylation of pyrrole with aryl iodides under ligand-free conditions
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A simple, inexpensive and ligand-free copper-catalysed N-arylation of pyrrole with aryl iodides has been developed giving N-arylated products in moderate to excellent yields. The catalyst loading is relative low (5 mol%) and the catalyst system was stable in air.
- Liu, Lili,Wu, Fengtian,Liu, Yan,Xie, Jianwei,Dai, Bin,Zhou, Zhuoqiang
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p. 180 - 182
(2014/04/17)
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- L-(+)-Tartaric acid and choline chloride based deep eutectic solvent: An efficient and reusable medium for synthesis of N-substituted pyrroles via Clauson-Kaas reaction
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l-(+)-Tartaric acid-choline chloride based deep eutectic solvent has been found to be an effective promoted medium for Clauson-Kaas reaction of aromatic amines and 2,5-dimethoxytetrahydrofuran. Structurally diverse N-substituted pyrroles were obtained in high to excellent yields under mild conditions. The deep eutectic solvent is inexpensive, non-toxic, reusable and biodegradable.
- Wang, Ping,Ma, Fei-Ping,Zhang, Zhan-Hui
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p. 259 - 262
(2014/11/07)
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- New pyrrole derivatives with potent tubulin polymerization inhibiting activity as anticancer agents including hedgehog-dependent cancer
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We synthesized 3-aroyl-1-arylpyrrole (ARAP) derivatives as potential anticancer agents having different substituents at the pendant 1-phenyl ring. Both the 1-phenyl ring and 3-(3,4,5-trimethoxyphenyl)carbonyl moieties were mandatory to achieve potent inhi
- La Regina, Giuseppe,Bai, Ruoli,Coluccia, Antonio,Famiglini, Valeria,Pelliccia, Sveva,Passacantilli, Sara,Mazzoccoli, Carmela,Ruggieri, Vitalba,Sisinni, Lorenza,Bolognesi, Alessio,Rensen, Whilelmina Maria,Miele, Andrea,Nalli, Marianna,Alfonsi, Romina,Di Marcotullio, Lucia,Gulino, Alberto,Brancale, Andrea,Novellino, Ettore,Dondio, Giulio,Vultaggio, Stefania,Varasi, Mario,Mercurio, Ciro,Hamel, Ernest,Lavia, Patrizia,Silvestri, Romano
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p. 6531 - 6552
(2014/10/16)
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- Synthesis of pyrrole derivatives from diallylamines by one-pot tandem ring-closing metathesis and metal-catalyzed oxidative dehydrogenation
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A series of aryl-substituted pyrrole derivatives was synthesized from diallylamines through a ruthenium carbene catalyzed ring-closing metathesis reaction and in situ oxidative dehydrogenation reaction catalyzed by FeCl 3·6H2O or CuCl2·2H2O in the presence of O2. The reaction was mild, simple, and convenient. An oxygen atmosphere played a critical role in obtaining high conversion of substituted pyrroles in the proposed catalytic system.
- Chen, Weiqiang,Wang, Jianhui
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supporting information
p. 1958 - 1963
(2013/05/08)
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- Squaric acid catalyzed simple synthesis of N-substituted pyrroles in green reaction media
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An operationally simple and efficient protocol for squaric acid catalyzed synthesis of N-substituted pyrroles via the reaction of 2,5- dimethoxytetrahydrofuran and 2,5-hexandione with aryl amines in green reaction media (water, deep eutectic solvent, and polyethylene glycol) under ultrasound irradiation or thermal conditions in good to excellent yields has been developed.
- Azizi, Najmadin,Davoudpour, Anahita,Eskandari, Farshid,Batebi, Ehlham
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p. 405 - 409
(2013/05/09)
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- A recyclable magnetic nanoparticles supported antimony catalyst for the synthesis of N-substituted pyrroles in water
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A new magnetic nanoparticle-supported antimony catalyst was prepared and evaluated as a recoverable catalyst for Clauson-Kaas reaction. The reaction proceeds efficiently in aqueous medium to give the corresponding N-substituted pyrroles in high yield. The immobilized catalyst could be easily recovered by magnetic separation and recycled for six times without significant loss of its catalytic activity.
- Ma, Fei-Ping,Li, Pei-He,Li, Bao-Le,Mo, Li-Ping,Liu, Ning,Kang, Hui-Jun,Liu, Ya-Nan,Zhang, Zhan-Hui
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- Unique chemoselective Clauson-Kass reaction of substituted aniline catalyzed by MgI2 etherate
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Clauson-Kass reaction of various substituted aniline, primary aryl amide, and sufonyl amide with 2,5-dimethoxytetrahydrofuran was realized in the presence of 10 mol % of MgI2 etherate in a mild, efficient, and highly chemoselective manner. Iodide counterion and solvents (i.e., MeCN) played the critical roles for the unique reactivity of this catalytic system.
- Zhang, Xingxian,Shi, Junchen
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experimental part
p. 898 - 903
(2011/03/19)
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- A microwave-assisted, green procedure for the synthesis of N-aryl sulfonyl and N-aryl pyrroles
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A simplified approach to the uncatalyzed Paal-Knorr condensation using microwave irradiation in water is described.
- Wilson, Matthew A.,Filzen, Gary,Welmaker, Gregory S.
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experimental part
p. 4807 - 4809
(2009/10/26)
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- Iron-catalyzed inexpensive and practical synthesis of N-substituted pyrroles in water
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An operationally simple, practical, and economical protocol for iron(III) chloride catalyzed Paal-Knorr pyrrole synthesis in water in good to excellent yields has been developed. Several N-substituted pyrroles are readily prepared from the reaction of 2,5-dimethoxytetrahydrofuran and aryl/alkyl, sulfonyl and acyl amines under very mild reaction conditions. Georg Thieme Verlag Stuttgart.
- Azizi, Najmedin,Khajeh-Amiri, Alireza,Ghafuri, Hossein,Bolourtchian, Mohammad,Saidi, Mohammad Reza
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experimental part
p. 2245 - 2248
(2009/12/03)
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- Scandium triflate-catalysed synthesis of N-substituted pyrroles from amine and 2,5-dimethoxytetrahydrofuran
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The Clauson-Kass pyrrole synthesis catalysed by scandium triflate afforded N-substituted 2- and 3-unsubstituted pyrroles with yields ranged from good to excellent. Aromatic amines, heteroaomatic amines, 4-methylbenzenesulfonamide and 2-chlorobenzamide are good substrates in this transformation.
- Zuo, Bing,Chen, Jiuxi,Liu, Miaochang,Ding, Jinchang,Wu, Huayue,Su, Weike
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experimental part
p. 14 - 16
(2009/09/25)
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- Practical copper-catalyzed N-arylation of nitrogen heterocycles with aryl halides under ligand and additive free conditions
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N-arylation of a wide variety of nitrogen heterocycles with aryl iodides catalyzed by copper iodide under mild ligand and additive free conditions (nBu4NBr, PhMe, NaOH, reflux, 22 h) was accomplished in good to excellent yields (up to 95%) and substrate conversions (up to 99%).
- Chang, Joyce Wei Wei,Xu, Xiuhui,Chan, Philip Wai Hong
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p. 245 - 248
(2007/10/03)
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- Reversion of Paal-Knorr synthesis: A new strategy for ring-opening and N-substituent change in 1H-pyrroles
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1H-Pyrroles were converted into 1,4-dicarbonyl compounds, and then into 1H-pyrroles with a different N-substituent by heating at 110 °C under nitrogen in 0.3 M sodium citrate buffer, pH 3, and in the presence of alkyl or aryl amines. The new pyrroles were obtained in low to very high yields depending upon the pH, the reaction time, the initial pyrrole and amine involved, and the proportion between both reagents. Georg Thieme Verlag Stuttgart.
- Zamora, Rosario,Hidalgo, Francisco J.
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p. 1428 - 1430
(2007/10/03)
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- Phenylpyrroles, a new chemolibrary virtual screening class of 5-HT 7 receptor ligands
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Virtual screening studies have identified a series of phenylpyrroles as novel 5-HT7 receptor ligands. The synthesis and the affinity for the 5-HT7 receptor of these phenylpyrroles are described. Some of these compounds exhibited high affinity for the 5-HT7 receptors.
- Paillet-Loilier, Magalie,Fabis, Frederic,Lepailleur, Alban,Bureau, Ronan,Butt-Gueulle, Sabrina,Dauphin, Francois,Delarue, Catherine,Vaudry, Hubert,Rault, Sylvain
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p. 3753 - 3757
(2007/10/03)
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- Copper-diamine-catalyzed N-arylation of pyrroles, pyrazoles, indazoles, imidazoles, and triazoles
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This paper details the copper-catalyzed N-arylation of π-excessive nitrogen heterocycles. The coupling of either aryl iodides or aryl bromides with common nitrogen heterocycles (pyrroles, pyrazoles, indazoles, imidazoles, and triazoles) was successfully performed in good yield with catalysts derived from diamine ligands and CuI. General conditions were found that tolerate functional groups such as aldehydes, ketones, alcohols, primary amines, and nitriles on the aryl halide or heterocycle. Hindered aryl halides or heterocycles were also found to be suitable substrates using the conditions reported herein.
- Antilla, Jon C.,Baskin, Jeremy M.,Barder, Timothy E.,Buchwald, Stephen L.
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p. 5578 - 5587
(2007/10/03)
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- Reductive one batch synthesis of N-substituted pyrrolidines from primary amines and 2,5-dimethoxytetrahydrofuran
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The construction of the pyrrolidine ring about a nitrogen of a primary amine by a reductive condensation reaction using 2,5- dimethoxytetrahydrofuran and sodium borohydride in acidic water medium is described. The reaction is fast, affords good to excellent yields and appears insensitive to electron effects and severe steric hindrance; it is found to be compatible with a large variety of aryl substituents, including nitro and oxo groups. The reaction allows the introduction of two deuterium atoms, with label conservation, in both the α-positions of the pyrrolidine ring by the use of sodium borodeuteride instead of sodium borohydride.
- Verardo, Giancarlo,Dolce, Anna,Toniutti, Nicoletta
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