- Structural reorganization of allyl isothiocyanate into pyrrole ring under superbase: A straightforward access to NH-2-(Alkylsulfanyl)-1H-pyrroles and N-Alkyl-2-(alkylsulfanyl)-1H-pyrroles
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A novel and facile synthetic route to NH-2-(alkylsulfanyl)-1H-pyrroles and N-alkyl-2-(alkylsulfanyl)-1H-pyrroles is reported. This was achieved by deprotonation of allyl isothiocyanate with the superbasic pair lithium diisopropylamide and potassium tert-butoxide (1:1 molar mixture), followed by intramolecular ring closure, deprotonation of cyclic anion with a second equivalent of the superbase, and final sequential N-protolysis/S-alkylation or N,S-dialkylation of the formed N,S-centered pyrrol-2-ylsulfide dianion. Georg Thieme Verlag Stuttgart · New York.
- Nedolya, Nina A.,Brandsma, Lambert,Trofimov, Boris A.
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Read Online
- Copper-Catalyzed Synthesis of Indolyl Benzo[b]carbazoles and Their Photoluminescence Property
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A copper-catalyzed cascade cyclization of dihydroisobenzofurans with indoles for the rapid construction of indoly benzo[b]carbazoles has been reported, providing the desired products in moderate to good yields under mild conditions along with a broad substrate scope and good functional group tolerance. The photoluminescence property of these indoly benzo[b]carbazoles has also been investigated.
- Hao, Tonggang,Huang, Long,Wei, Yin,Shi, Min
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supporting information
p. 5133 - 5137
(2021/07/19)
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- Anti-inflammatory COX/LOX inhibitor, and preparation method and application thereof
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The invention provides an anti-inflammatory COX/LOX inhibitor, and a preparation method and an application thereof. The inhibitor is a compound represented by formula I, or a pharmaceutically acceptable salt thereof. The novel anti-inflammatory COX/LOX inhibitor can significantly reduce the ear swelling degree of mice in an administrated group in xylene-induced ear swelling test, so the compound has an anti-inflammatory effect, and the anti-inflammatory effect of the compound is equivalent with that of aspirin; and additionally, pharmacological tests show that the compound has small irritationto the gastrointestinal tract. The preparation method of the novel anti-inflammatory COX/LOX inhibitor has the advantages of simplicity, easiness in operation, and effectiveness in the reduction of the production cost to realize industrial production.
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Paragraph 0046; 0047-0048
(2019/04/10)
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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 0059; 0060
(2018/10/04)
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- Synthesis method of N-methylpyrrole
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The invention discloses a synthesis method of N-methylpyrrole. The method comprises the step of enabling butanedial and methylamine to be subjected to a heating reaction under the alkaline condition so as to obtain the N-methylpyrrole. Compared with the prior art, the synthesis method provided by the invention has the characteristics of being short in reaction route, low in cost, relative mild inreaction condition, high in reaction yield, and the like; the method is simple to operate and convenient in aftertreatment, thus having industrial application prospect.
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Paragraph 0012; 0026; 0027; 0028; 0030; 0032
(2018/07/15)
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- Selective catalytic transfer dehydrogenation of alkanes and heterocycles by an iridium pincer complex
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Catalytic alkane dehydrogenation is a reaction with tremendous potential for application. We describe a highly active PSCOP-pincer iridium catalyst for transfer dehydrogenation of cyclic and linear alkanes. The dehydrogenation of linear alkanes occurs under relatively mild conditions with high regioselectivity for a-olefin formation. In addition, the catalyst system is very effective in the dehydrogenation of heterocycles to form heteroarenes and olefinic products.
- Yao, Wubing,Zhang, Yuxuan,Jia, Xiangqing,Huang, Zheng
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supporting information
p. 1390 - 1394
(2014/03/21)
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- Green N-methylation of electron deficient pyrroles with dimethylcarbonate
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The N-methylation of electron-deficient pyrroles was affected using dimethyl carbonate in the presence of DMF and catalytic DABCO. This alkylation methodology has proven useful for the alkylation of a variety of pyrroles in 72-98% yields and is considered to be green chemistry relative to the more common use of methyl halides or dimethyl sulfate.
- Laurila, Michael L.,Magnus, Nicholas A.,Staszak, Michael A.
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experimental part
p. 1199 - 1201
(2010/04/22)
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- Superbase-promoted direct N-carbonylation of pyrrole with carbonic acid diesters
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Carbonic acid diesters have been investigated as carbonylating agents in the direct reaction with pyrrole (HetNH). In the presence of superbases (DBU, P1-t-Bu, BTPP) as catalysts, the heteroaromatic substrate can be N-carbonylated by direct reaction with carbonic acid diesters under not-severe experimental conditions. The carbonylation reaction makes accessible pyrrole N-carbonyl derivatives (HetNC(O)OR, (HetN)2CO) selectively through a simple straightforward way, which offers a safe eco-friendly alternative to the traditional synthetic methods based on hazardous phosgene or phosgene-derivatives.
- Carafa, Marianna,Distaso, Monica,Mele, Valentina,Trani, Francesca,Quaranta, Eugenio
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p. 3691 - 3696
(2008/09/20)
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- Incomparably easy migration of functionalized enol substituent in pyrrole ring
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Functionalized pyrrolebvbΕ enols, 2-(1-hydroxy-2.2-dicyanoethenyl)-1- methylpyrroles, at heating (75-135°C) unexpectedly readily rearranged in high yield into 3-isomers. Evidently the migration of the enol fragment involves a mesomeric zwitterion formed as a result of an intra- and intermolecular autoprotonation of the pyrrole ring by the acidic enol hydroxy group. Under similar conditions no migration of the ethenyl moiety occurred in 2-(1-hydroxy-2-carbamoyl-2-cyanoethenyl)-1-methylpyrroles. The quantum-chemical calculations (MP2/6-311G**) show a clear-cut distinction in the relative stability of 2- and 3-isomers of 1H- and 1- methylhydroxyethenylpyrroles: in the former case the 2-isomer is more stable, whereas in the 1-methyl-substituted compound, the 3-isomer.
- Sobenina,Drichkov,Petrova,Ushakov,Kashik,Krivdin,Rusakov,Zykova,Mikhaleva,Trofimov
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p. 237 - 246
(2008/12/20)
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- Potassium carbonate as a base for the N-alkylation of indole and pyrrole in ionic liquids
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The methodology for the N-alkylation of indole and pyrrole using potassium carbonate in 1-n-butyl-3-methylimidazolium tetrafluoroborate [bmim][BF4] as the sustainable reaction media with acetonitrile as the cosolvent is described herein. Our approach provides good yields with alkyl halides as well as sulfonates as the electrophiles. Cesium carbonate was also found to be a consistent base in the N-alkylation. The proposed methodology is simple and mild with easy workup.
- Jorapur, Yogesh R.,Jeong, Jae Min,Chi, Dae Yoon
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p. 2435 - 2438
(2007/10/03)
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- N-methylation of nitrogen-containing heterocycles with dimethyl carbonate
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Reactivity of dimethyl carbonate, the environmentally friendly reagent, as methylating agent for nitrogen-containing heterocyclic compounds has been studied. Reactions of imidazole, pyrazole, pyrrole, morpholine, and piperazine with dimethyl carbonate to afford N-methylated products were reported. The reactions were carried out with neither catalyst nor solvent at a temperature range of 110-170°C under atmospheric pressure. Copyright Taylor & Francis, Inc.
- Ouk, Samedy,Thiebaud, Sophie,Borredon, Elisabeth,Chabaud, Bernard
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p. 3021 - 3026
(2007/10/03)
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- Organic reactions in ionic liquids: A simple and highly regioselective N-substitution of pyrrole
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In ionic liquids [Bmim][PF6] or [Bmim][BF4], pyrrole replaced the halogen atom of an alkyl halide to give the corresponding N-substituted pyrrole in excellent yield. Benzenesulfonyl chloride, p-methylbenzenesulfonyl chloride and benzoyl chloride reacted similarly with pyrroles to afford the N-substituted pyrroles in quantitative yield. Michael addition reaction of pyrrole with electrophilic olefins was completed in a highly regioselective manner to afford the N-alkylpyrroles.
- Le, Zhang-Gao,Chen, Zhen-Chu,Hu, Yi,Zheng, Qin-Guo
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p. 1951 - 1954
(2007/10/03)
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- 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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p. 2405 - 2408
(2007/10/03)
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- Novel synthesis of enamines by iridium-catalyzed dehydrogenation of tertiary amines
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A novel route to enamines is reported, the dehydrogenation of tertiary amines catalyzed by a "pincer-ligated" iridium catalyst.
- Zhang, Xiawei,Fried, Amy,Knapp, Spencer,Goldman, Alan S.
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p. 2060 - 2061
(2007/10/03)
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- Heterocyclic compounds as ligands of the GABAA receptor
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Disclosed are heterocyclic compounds of the formula and the pharmaceutically acceptable salts thereof wherein the variables A, V, Y, J, E, X, T, G, Q, W, Z, b, n and m are defined herein. These compounds are highly selective agonists, antagonists or inverse agonists for GABAA brain receptors or prodrugs of agonists, antagonists or inverse agonists for GABAA brain receptor.
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- Chloropyridylcarbonyl derivatives
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Novel chloropyridylcarbonyl derivatives of the formula STR1 in which Het is STR2 n is 1 or 2, R1 is hydrogen, optionally substituted C1-6 alkyl, optionally substituted C2-6 alkenyl, optionally substituted C3-6 alkynyl, optionally substituted phenyl or optionally substituted pyrimidinyl, and R2 and R3, independently of each other, are hydrogen or C1-4 alkyl, and acid addition salts and metal salt complexes thereof, are outstandingly active as microbicides.
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- Cyclopropylpyrroloindole-oligopeptide anticancer agents
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The invention is directed to novel cyclopropylpyrroloindole-oligopeptide compounds which are useful as anticancer agents. The novel cyclopropylpyrroloindole-oligopeptide compounds have the following general structure: STR1 wherein, Het1 and Het2 are individually selected from the group consisting of pyrrole, imidazole, triazole, thiophene, furan, thiazole, oxazole and pyrazole, R is selected from the group consisting of a valence bond; a C1 -C6 alkyl; a C2 -C6 alkenyl; a C2 -C6 alkynyl; and an ortho, meta or para linked aromatic group, A is selected from the group consisting of a C1 -C6 alkyl group; an amidine or derivative thereof; a guanidine; a secondary, tertiary or quaternary ammonium salt; and a sulfonium salt, n is 0 to 3, and m is 0 to 3.
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- A facile synthesis of N-substituted pyrroles
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Phosphorous pentoxide is the catalyst of choice for the facile conversion of primary amines, aromatic amines, sulfonamides and primary amides into the corresponding N-substituted pyrroles from 2,5-dimethoxytetrahydrofuran.
- Fang,Leysen,Ottenheijm
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p. 1857 - 1861
(2007/10/02)
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- Selective Alkylation of Pyrrole by Phase Transfer Catalysis in the Absence of Solvent
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Selective N-alkylation of pyrrole is performed, in good yield and by a very simple method, using Phase Transfer Catalysis in the absence of solvent.
- Diez-Barra, E.,Hoz, A. de la,Loupy, A.,Sanchez-Migallon, A.
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p. 1715 - 1718
(2007/10/02)
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- Acetylenes as Potential Antarafacial Components in Concerted Reactions. Formation of Pyrroles from Thermolyses of Propargylamines, of a Dihydrofuran from a Propargylic Ether, and of an Ethylidenepyrrolidine from a β-Amino Acetylene
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A thermal cyclization of acetylenic compounds provides evidence for the ability of acetylenic links to act as antarafacial components in processes.The cyclization competes with the normally favored acetylenic retro-ene reaction.Propargylic amines, without substituents whose presence would hinder a tight cyclic transition state, yield intermediate pyrrolines whose subsequent hydrogen elimination affords pyrroles in small amounts.The same process in 2-ethynyltetrahydropyran affords 8-oxabicyclooctane in 35percent yield.A related thermal reaction of N-methyl-3-hexyn-1-amine provides a quantitative transformation to N-methyl-2-ethylidenepyrrolidine in a nominal s + 2a + 2s + 2s> Moebius process, wherein the acetylenic unit is the antarafacial component.Evidence for concertedness in these reactions is discussed.
- Viola, Alfred,Collins, John J.,Filipp, Nicholas,Locke, John S.
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p. 5067 - 5075
(2007/10/02)
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- Kinetics and thermal degradation of the fructose-methionine Amadori intermediates. GC-MS/SPECMA data bank identification of volatile aroma compounds
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Fructose-methionine Amadori intermediates, prepared from D-glucose and L-methionine, were purified by semi-preparative HPLC.Structural elucidation was achieved by 13C-NMR and mass spectrometry in the FAB+ and FAB- modes.Constant rates of formation of glucosylamine and the Amadori intermediate, and their thermal degradation into reductones and methionine as well as into diglucosylamine, were observed.Thermal degradation of the Amadori intermediate gives not only the well-known degradation products of the sugar moiety and methional (from the Strecker degradation of methionine), but also several heterocyclic compounds (pyridines, pyrazines, pyrroles, and furans).Some of them contain a methylthiopropyl group in their side chain.These new compounds were identified by the fragmentation rules and Kovats additive properties.Out of the 80 compounds isolated, ca. 70 were identified.
- Vernin, Gaston,Metzger, Jacques,Boniface, Christian,Murello, Marie-Helene,Siouffi, Antoine,et al.
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- The flash vacuum thermolysis of (-)-cocaine
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(-)-Cocaine is thermally labile and, in a series of remarkable thermal reactions, is cleanly partitioned among benzoic acid, N-methylpyrrole and methyl 3-butenoate.
- Sisti,Fowler,Fowler
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p. 5977 - 5980
(2007/10/02)
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- PHASE TRANSFER CATALYSIS WITHOUT SOLVENT. USE OF ALKYL IODIDES.
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The Phase Transfer Catalysis (PTS) without solvent method allows the use of quaternary ammonium salts (QAS) when alkyl iodides are used.
- Diez-Barra, E.,Hoz, A. de la,Sanchez-Migallon, A.,Sanchez-Verdu, P.,Bram, G.,et al.
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p. 293 - 296
(2007/10/02)
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- Thermolysis of Polyazapentadienes. Part 8. The formation of Pyrroles from 1,1-Dialkyl-5-aryl-1,5-diazapentadienes
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Flash vacuum pyrolysis of the 1,5-diazapentadienes (4)-(10) gave moderate yields of pyrroles together with quinolines, formed by electrocyclic ring closure with elimination.The pyrroles were formed by hydrogen transfer from an N-alkyl group, followed by cyclisation and final aromatisation of the resulting dihydropyrrole intermediate by free-radical cleavage.The mechanism of the hydrogen transfer and cyclisation is not known with certainty, but may involve diradicals or 1,5-dipolar intermediates.
- McNab, Hamish,Murray, M. Elizabeth-Ann
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p. 333 - 338
(2007/10/02)
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- A Convenient and One-pot Synthesis of 9-Substituted Carbazoles from Primary Amine Hydrochlorides and 2,5-Dimethoxytetrahydrofuran
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Carbazoles are the very important compounds in material science, nevertheless conventional syntheses required severe and very complicated reaction conditions.In the process of preparation of pyrrole derivatives, we found that a primary amine hydrochloride 1 and 2,5-dimethoxytetrahydrofuran 2 were refluxed in benzene-water (100:4 (v/v)) mixture to be obtained 9-substituted carbazole 5 in a high yield.This method is the one-pot synthesis of 9-substituted carbazoles 5 under mild and convenient conditions.
- Kashima, Choji,Hibi, Shigeki,Maruyama, Tatsuya,Harada, Kazuo,Omote, Yoshimori
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p. 913 - 916
(2007/10/02)
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- 10 Oxo-4,5-dihydro-10H-benzo 5,6 cycloheph[1,2-B]pyrryls
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A compound of formula (II): STR1 wherein R is a C1-4 alkyl group; R1 is a hydrogen atom or a C1-4 alkyl group; R2 is a hydrogen or halogen atom, or a C1-4 alkyl, C1-4 alkoxy or C1-4 alkylthio group; and pro-drugs thereof; and the pharmaceutically acceptable salts of the compounds of formula (II) and of their pro-drugs; has useful anti-inflammatory and analgesic activity.
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- Indolyl phthalide compounds
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3-Aryl-3-indolylphthalides, 3-aryl-3-pyrrolylphthalides and 3-aryl-3-carbazolylphthalides prepared by interaction of the appropriate 2-(heteroaryl)carbonylbenzoic acid and the appropriate phenylamine, and 3,3-bis(indolyl)phthalides prepared by the interaction of the appropriate 2-(indolyl)carbonylbenzoic acid and the appropriate indole are useful as color formers in pressure-sensitive carbonless duplicating systems, thermal marking systems and hectographic copying systems.
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- Gas-Phase Heteroaromatic Substitution. 2. Electrophilic Methylation of Pyrrole and N-Methylpyrrole by CH3XCH3+ (X = F or Cl) Ions
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The gas-phase methylation of pyrrole (1) and N-methylpyrrole (2) by CH3XCH3+ (X = F or Cl) ions, from the γ radiolysis of CH3X, has been investigated at pressure ranging from 50 to 760 torr, in the presebce of a thermal radical scavenger (O2) and variable concentrations of an added base (NMe3).Both the reactivity of the selected pyrroles relative to benzene, used as the refernce substrate in competition experiments, and the isomeric distribution of their methylated derivatives depende markedly on the total pressure of the system and the concentration of NMe3.The apparent kP/kB ratios increase from 0.2 (1)-0.3 (2), in neat CH3F at 50 torr, to over 0.4 (1)-1.0 (2), at 760 torr containing 10 torr of NMe3.Concurently, the isomeric distribution of the methylated products changes from β:α:N = 80percent:13percent:7percent (from 1) and β:α = 65percent:35percent (from 2) to β:α:N = 50percent:15percent:35percent and β:α = 70percent:30percent.These results are consistent with a methylation mechanism involving kinetically predominant CH3FCH3+ attack on the β-carbons of the pyrrolic substrate and subsequent isomerization of the resulting excited intermediates to the thermodynamically most stable 3-methylpyrrole protonated on the 2-position.The substrate and positional selectivity of the gas-phase methylation and the mechanism of isomerization that appears of intramolecular nature are discussed in the light of the recent theoretical predictions on heteroaromatic reactivity and compared with the available data of related methylation reactions, occuring both in the gaseous and condensed phase.
- Angelini, Giancarlo,Sparapani, Cinzia,Speranza, Maurizio
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p. 7084 - 7091
(2007/10/02)
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- Novel compounds, processes and marking systems
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Mono and bis substituted (arylsulfonyl)alkanes useful as color formers, particularly in carbonless duplicating and thermal marking systems, are prepared by the interaction of the appropriate aldehyde or dialdehyde with the appropriate aryl or heterocyclic moiety and the appropriate phenylsulfinic acid in the presence of a catalyst.
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- Heteroarylphthalides
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3-Aryl-3-indolylphthalides, 3-aryl-3-pyrrolylphthalides and 3-aryl-3-carbazolylphthalides prepared by interaction of the appropriate 2-(heteroaryl)carbonylbenzoic acid and the appropriate phenylamine, and 3,3-bis(indolyl)-phthalides prepared by the interaction of the appropriate 2-(indolyl)carbonylbenzoic acid and the appropriate indole are useful as color formers in pressure-sensitive carbonless duplicating systems, thermal marking systems and hectographic copying systems.
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- Phthalide compounds, processes and marking systems
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3-Aryl-3-indolylphthalides, 3-aryl-3-pyrrolylphthalides and 3-aryl-3-carbazolylphthalides prepared by interaction of the appropriate 2-(heteroaryl)carbonylbenzoic acid and the appropriate phenylamine, and 3,3-bis(indolyl)phthalides prepared by the interaction of the appropriate 2-(indolyl)carbonylbenzoic acid and the appropriate indole are useful as color formers in pressure-sensitive carbonless duplicating systems, thermal marking systems and hectographic copying systems.
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- Anomalous Products from 1,2,5-Triaza- and 1,5-Diaza-pentadiene Thermolyses: Formation of Amidines and Pyrroles, respectively
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Gas-phase thermolysis of the dimethylaminoazoalkene (1) gives the formamidine (2) by loss of HCN: in contrast, the related 1,5-diazapentadiene (4) under more forcing conditions gives aniline (30percent) and N-methylpyrrole (43percent).
- McNab, Hamish,Murray, Elizabeth-Ann
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p. 722 - 723
(2007/10/02)
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- Bromination and Chlorination of Pyrrole and Some Reactive 1-Substituted Pyrroles
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Monobromination of pyrrole and 1-methyl-, 1-benzyl-, and 1-phenylpyrrole with 1 mol of N-bromosuccinimide in tetrahydrofuran results in the regiospecific formation of the 2-bromopyrroles.A little disubstitution is observed.Similarly, brominations with 2, 3, or 4 mol of NBS form primarily the di-, tri-, and tetrabromopyrroles, respectively.The thermodynamically more stable 3-bromopyrroles are the major monobrominated products observed when bromine is used as the brominating agent due to isomerization of the 2-bromopyrroles with hydrogen bromide.These reaction mixtures are further complicated because of disproportionation reactions.Chlorination with N-chlorosuccinimide gave results similar to those for the bromination with NBS, but the reaction is not as selective.
- Gilow, H. M.,Burton, D. Edward
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p. 2221 - 2225
(2007/10/02)
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- A NOVEL SYNTHESIS OF PYRROLES BY THE REACTIONS OF TRIS(ALKYLTHIO)CYCLOPROPENIUM SALT WITH AMINES
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"One pot" synthesis of 2,3-bis(alkylthio)pyrroles in 45 - 80percent yields under mild conditions was achieved by the reactions of tris(tert-butylthio)cyclopropenium salt (1) with secondary amines in the presence of t-BuOK in DMF.Although the reaction of 1 with primary amine such as methylamine gave only the ring opening product, the use of primary amines having structure of XCH2NH2 (X=CN, COOMe, Ph) resulted in the formation of the pyrroles bearing the substituent at the α-position in 44 - 71percent yields.
- Yoneda, Shigeo,Hirai, Hideo,Yoshida, Zen-ichi
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p. 865 - 869
(2007/10/02)
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- First Example of Predominant β-Orientation in Electrophilic Substitution of Pyrrole
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The isomeric distribution of the neutral products from the gas-phase electrophilic attack of 3He3H+, CH3FCH3+, and t-C4H9+ ions on pyrrole provides the first experimental evidence for predominant β-orientation in electrophilic substitution of pyrrole .
- Speranza, Maurizio
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p. 1177 - 1178
(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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