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Journal articles on the topic 'Pyrroles. Organic compounds'

Author: Grafiati

Published: 4 June 2021

Last updated: 9 February 2022

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1

Iqbal, Sarosh, Hina Rasheed, Rabiya Javed Awan, Ramsha Javed Awan, Asma Mukhtar, and Mark G. Moloney. "Recent Advances in the Synthesis of Pyrroles." Current Organic Chemistry 24, no. 11 (2020): 1196–229. http://dx.doi.org/10.2174/1385272824999200528125651.

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: Pyrroles are the most prevalent heterocyclic compounds, which are present as the basic cores in many natural products, such as vitamin B12, bile pigments like bilirubin and biliverdin, the porphyrins of heme, chlorophyll, chlorins, bacteriochlorins, and porphyrinogens. The biological activities of compounds having pyrrole analogs include antimicrobial (antibacterial, antifungal), anti-cancer (anti-cytotoxic, antimitotic), anti-tumor, anti-hyperlipidemic, anti-depressant, anti-inflammatory, antihyperglycemic, antiproliferative, anti-HIV and anti-viral activities. Accordingly, significant atte

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2

Gao, Meng, Wenting Zhao, Hongyi Zhao, Ziyun Lin, Dongfeng Zhang, and Haihong Huang. "An efficient and facile access to highly functionalized pyrrole derivatives." Beilstein Journal of Organic Chemistry 14 (April 20, 2018): 884–90. http://dx.doi.org/10.3762/bjoc.14.75.

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A straightforward and one-pot synthesis of pyrrolo[3,4-c]pyrrole-1,3-diones via Ag(I)-catalyzed 1,3-dipolar cycloaddition of azomethine ylides with N-alkyl maleimide, followed by readily complete oxidation with DDQ, has been successfully developed. Further transformation with alkylamine/sodium alkoxide alcohol solution conveniently afforded novel polysubstituted pyrroles in good to excellent yields. This methodology for highly functionalized pyrroles performed well over a broad scope of substrates. It is conceivable that this efficient construction method for privileged pyrrole scaffolds could

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3

Xuan, Duc Dau. "Recent Progress in the Synthesis of Pyrroles." Current Organic Chemistry 24, no. 6 (2020): 622–57. http://dx.doi.org/10.2174/1385272824666200228121627.

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: Pyrrole derivatives are nitrogen-containing heterocyclic compounds and widely distributed in a large number of natural and non-natural compounds. These compounds possess a broad spectrum of biological activities such as anti-infammatory, antiviral, antitumor, antifungal, and antibacterial activities. Besides their biological activity, pyrrole derivatives have also been applied in various areas such as dyes, conducting polymers, organic semiconductors. : Due to such a wide range of applicability, access to this class of compounds has attracted intensive research interest. Various established

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4

Palmieri, Alessandro, and Marino Petrini. "Synthesis and practical applications of 2-(2-nitroalkyl)pyrroles." Organic & Biomolecular Chemistry 18, no. 24 (2020): 4533–46. http://dx.doi.org/10.1039/d0ob00956c.

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Two main approaches can be designed for the synthesis of 2-(2-nitroalkyl)pyrroles using nitroalkenes or nitroalkanes in the reaction with pyrrole derivatives. The obtained nitroalkyl pyrroles can be converted into various bioactive compounds.

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5

Philkhana, Satish Chandra, Fatimat O. Badmus, Isaac C. Dos Reis, and Rendy Kartika. "Recent Advancements in Pyrrole Synthesis." Synthesis 53, no. 09 (2021): 1531–55. http://dx.doi.org/10.1055/s-0040-1706713.

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AbstractThis review article features selected examples on the synthesis of functionalized pyrroles that were reported between 2014 and 2019. Pyrrole is an important nitrogen-containing aromatic heterocycle that can be found in numerous compounds of biological and material significance. Given its vast importance, pyrrole continues to be an attractive target for the development of new synthetic reactions. The contents of this article are organized by the starting materials, which can be broadly classified into four different types: substrates bearing π-systems, substrates bearing carbonyl and ot

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6

Huang, Wenbo, Kaimei Wang, Ping Liu, Minghao Li, Shaoyong Ke та Yanlong Gu. "Three-component reactions of aromatic amines, 1,3-dicarbonyl compounds, and α-bromoacetaldehyde acetal to access N-(hetero)aryl-4,5-unsubstituted pyrroles". Beilstein Journal of Organic Chemistry 16 (30 листопада 2020): 2920–28. http://dx.doi.org/10.3762/bjoc.16.241.

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N-(Hetero)aryl-4,5-unsubstituted pyrroles were synthesized from (hetero)arylamines, 1,3-dicarbonyl compounds, and α-bromoacetaldehyde acetal by using aluminum(III) chloride as a Lewis acid catalyst through [1 + 2 + 2] annulation. This new versatile methodology provides a wide scope for the synthesis of different functional N-(hetero)aryl-4,5-unsubstituted pyrrole scaffolds, which can be further derived to access multisubstituted pyrrole-3-carboxamides. In the presence of 1.2 equiv of KI, a polysubstituted pyrazolo[3,4-b]pyridine derivative was also successfully synthesized.

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7

Lakhlifi, Tahar, Ahmed Sedqui, Toufik Fathi, Bernard Laude, and Jean-François Robert. "Double diastéréosélectivité de la cycloaddition dipolaire-1,3 d'ylures d'azométhine cycliques substitués." Canadian Journal of Chemistry 72, no. 6 (1994): 1417–23. http://dx.doi.org/10.1139/v94-178.

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Seven derivatives of methyl 5-phenyl-3,4-dihydro-2H-pyrrole-2-carboxylates 1 were synthetized. These compounds are precursors of pentagonal cyclic azomethine ylids, the two sides of which are diastereotopic. The 1,3-dipolar species react with N-methyl and N-phenylmaleimides diastereospecifically. The approach of the reactant species occurs from the less hindered side of the 1,3-dipole and in endo to lead the thermodynamically stable exo cycloadduct. Moreover, oxidation of the compounds 1 gives the corresponding substituted pyrroles.

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8

Gogan, Niall J., Robert McDonald, Hugh J. Anderson, and Charles E. Loader. "Synthesis and spectroscopic studies of some substituted 3-benzoylpyrroles and their tricarbonylchromium complexes." Canadian Journal of Chemistry 67, no. 3 (1989): 433–36. http://dx.doi.org/10.1139/v89-067.

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3-Benzoylpyrroles with a substituent on the pyrrole ring have been synthesized. Both the iodination and chlorination gave only the 2,4 derivatives while isopropylation gave mixtures of the 2,4 and 2,3 compounds. No 3,4 compounds were obtained. Both steric and electronic effects seem to determine the substitution pattern. The Cr(CO)3 complexes (Cr on the benzene ring) were prepared and these complexes, together with the uncomplexed pyrroles, were studied by IR, 1H-NMR, and ESR of the radical anions from the N-methylpyrrole derivatives. For the 2,4 compounds, the substituent on the pyrrole ring

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9

Sobenina, L. N., A. I. Mikhaleva, and B. A. Trofimov. "Synthesis of pyrroles from heterocyclic compounds (review)." Chemistry of Heterocyclic Compounds 25, no. 3 (1989): 237–53. http://dx.doi.org/10.1007/bf00472377.

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10

Chang, Xiangqing, Xiaofeng Yang, Zhiwei Chen, and Weihui Zhong. "1,4-Diazabicyclo[2.2.2]octane-Catalyzed Multicomponent Domino Strategy for the Synthesis of Tetrasubstituted NH-Pyrroles." Synlett 30, no. 12 (2019): 1431–36. http://dx.doi.org/10.1055/s-0037-1611857.

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A mild and efficient 1,4-diazabicyclo[2.2.2]octane (DABCO)-catalyzed three-component domino reaction was developed for the synthesis of highly functionalized NH-pyrroles from arylglyoxal monohydrates, enamino esters, and cyclic 1,3-dicarbonyl compounds in 1,4-dioxane at room temperature for 0.5 hours. Various substituted NH-pyrroles were obtained in moderate to good yields.

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11

Li, Jin-Heng, De-Lie An, and Jing-Hao Qin. "Recent Advances in Cycloaddition Reactions with Alkynes to Construct Heterocycles." Synthesis 52, no. 24 (2020): 3818–36. http://dx.doi.org/10.1055/s-0040-1707355.

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Heterocyclic compounds, especially N-heterocycles and O-heterocycles, are prominent structural motifs present in numerous natural products and medically and/or economically important compounds. This review aims to describe the development of transition-metal-catalyzed cycloaddition reactions of functionalized m-atom partners with alkynes to access a wide range of five-, six-, and seven-membered heterocycles, that is functionalized N-heterocycles and O-heterocycles such as azepines, isoquinolines, isocoumarins, spiroheterocycles, indoles, furans, and pyrroles, in a selectively controlled manner

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12

Portilla Zuniga, Omar Miguel, Angel Gabriel Sathicq, Jose Jobanny Martinez Zambrano, and Gustavo Pablo Romanelli. "Green Synthesis of Pyrrole Derivatives." Current Organic Synthesis 14, no. 6 (2017): 865–82. http://dx.doi.org/10.2174/1570179414666161206124318.

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Background: Pyrroles are organic cyclic compounds with an extensive and fascinating chemistry. These compounds have a wide structural variety and they are an important basis in technological development as they can be used as drugs, dyes, catalysts, pesticides, etc. Therefore, the production of these heterocyclic compounds by efficient clean methodologies is a great achievement in contemporary chemistry. In this paper, we show recent green procedures in the synthesis of pyrrole derivatives such as Hantzsch, Knorr and Paal- Knorr syntheses, as well as new eco-friendly synthetic procedures with

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13

Giubellina, Nicola, Wim Aelterman, and Norbert De Kimpe. "Use of 3-halo-1-azaallylic anions in heterocyclic chemistry." Pure and Applied Chemistry 75, no. 10 (2003): 1433–42. http://dx.doi.org/10.1351/pac200375101433.

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The synthetic potential of lithio 3-halo-1-azaallylic anions as building blocks in organic chemistry and especially in heterocyclic chemistry will be highlighted by the synthesis of functionalized imines, obtained after reaction of 3-halo-1-azaallylic anions with het- eroatom-substituted electrophiles. Thus, the latter generated functionalized imines are suitable building blocks for the synthesis of a whole range of heterocycles and physiologically active compounds, including agrochemicals and pharmaceuticals. 3-Halo-1-azaallylic anions were used in the synthesis of N-alkyl-3,3-dichloroazetidi

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14

Karadeniz, Eda, та Metin Zora. "Synthesis of 1-Azaspiro[4.5]deca-1,3-dienes from N-Propargylic β-Enaminones in Basic Medium". Synthesis 51, № 10 (2019): 2157–70. http://dx.doi.org/10.1055/s-0037-1611723.

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A facile, efficient and unprecedented method for the synthesis of spiro-2H-pyrroles is reported. When reacted with 1-ethynylcyclohexylamine, α,β-alkynic ketones produced cyclohexane-embedded N-propargylic β-enaminones, which in the presence of cesium carbonate underwent nucleophilic cyclization to afford 1-azaspiro[4.5]deca-1,3-diene derivatives in good to excellent yields. This cyclization was found to be general for a variety of cyclohexane-embedded N-propargylic β-enaminones and demonstrated good tolerance to a broad range of aliphatic, aromatic and heteroaromatic groups with electron-withd

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15

Shahvelayati, Ashraf S., Maryam Ghazvini, Khadijeh Yadollahzadeh та Akram S. Delbari. "A Phosphine-mediated Synthesis of 2,3,4,5-tetra-substituted Nhydroxypyrroles from α-oximino Ketones and Dialkyl Acetylenedicarboxylates Under Ionic Liquid Green-media". Combinatorial Chemistry & High Throughput Screening 21, № 1 (2018): 14–18. http://dx.doi.org/10.2174/1386207321666180124094536.

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Background: The development of multicomponent reactions (MCRs) in the presence of task-specific ionic liquids (ILs), used not only as environmentally benign reaction media, but also as catalysts, is a new approach that meet with the requirements of sustainable chemistry. In recent years, the use of ionic liquids as a green media for organic synthesis has become a chief study area. This is due to their unique properties such as non-volatility, non-flammability, chemical and thermal stability, immiscibility with both organic compounds and water and recyclability. Ionic liquids are used as enviro

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16

Chaudhary, Ankita. "Arylglyoxals as Versatile Synthons for Heterocycles Through Multi-Component Reactions." Current Organic Chemistry 23, no. 18 (2019): 1945–83. http://dx.doi.org/10.2174/1385272823666191019110010.

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Arylglyoxals are important synthons that have been used in the construction of a diverse spectrum of compounds. The use of multicomponent approaches in organic synthesis due to its environmentally friendly nature is a step forward towards sustainability. This review will offer the reader insightful perspectives on the use of arylglyoxals for the synthesis of various heterocyclic compounds like pyrroles, pyrazoles, furans, imidazoles, indoles, oxazoles, pyridines, quinazolines, pyrans, etc using multicomponent approach.

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17

Leinweber, P., G. Jandl, K. U. Eckhardt, et al. "Nitrogen speciation in fine and coarse clay fractions of a Cryoboroll - new evidence from pyrolysis-mass spectrometry and nitrogen K-edge XANES." Canadian Journal of Soil Science 90, no. 2 (2010): 309–18. http://dx.doi.org/10.4141/cjss09063.

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Soil clay fractions are usually enriched in nitrogen (N), but the chemical identity of this N is largely unknown. Therefore, we investigated organic N in fine and coarse clay of a clay-rich Cryoboroll by Curie-point pyrolysis-gas chromatography/mass spectrometry (Cp Py-GC/MS), Pyrolysis-field ionization mass spectroscopy (Py-FIMS) and synchrotron-based nitrogen K-edge X-ray absorption near edge structure (N-XANES) spectroscopy. The Cp Py-GC-MS revealed 30 structurally different N-containing compounds, such as substituted pyridines, pyrroles; pyrazines, pyrazoles, imidazoles, quinolines, side-c

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18

Krayushkin, Mikhail M., Valerii Z. Shirinian, Alexey A. Shimkin, Arthur K. Mailian, Anatoly V. Metelitsa, and Sergei O. Bezugliy. "Novel photochromic spiro compounds based on thieno[3,2-b ]pyrroles." Journal of Physical Organic Chemistry 20, no. 11 (2007): 845–50. http://dx.doi.org/10.1002/poc.1238.

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19

He, Jian-Ping, Zhen-Zhen Zhan, Nan Luo, Ming-Ming Zhang, and Guo-Sheng Huang. "Direct synthesis of 2,3,5-trisubstituted pyrroles via copper-mediated one-pot multicomponent reaction." Organic & Biomolecular Chemistry 18, no. 48 (2020): 9831–35. http://dx.doi.org/10.1039/d0ob01952f.

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Efficient condensation of 1,3-dicarbonyl compounds to give highly functionalized pyrroles in moderate to good yields from readily available starting materials and a wide range of substrates, by synergistic formation of new C–C and C–N bonds.

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20

Musaev, Yurii I., Eleonora B. Musaeva, Svetlana Yu Khashirova, Marina O. Sanakoeva, and Artur E. Baykaziev. "Synthesis of Aromatic Diketoximes and their Complexes with Nickel Salts." Key Engineering Materials 869 (October 2020): 571–76. http://dx.doi.org/10.4028/www.scientific.net/kem.869.571.

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The diketoximes of 4,4'-diacetyldiphenyl oxide and 4,4'-diacetyldiphenyl sulfide were synthesized, the possibility of their use for the synthesis of simple and complex polyesters and polypyrroles, as well as the ability to complex with nickel salts. Organic chemistry used oximes in the 19th century, afterward, as an analytical reagent in the 20th century. Currently, oximes are superior to carbonyl compounds and alcohols in the variety of reactions and the widespread use in synthetic chemistry. Oximes easily turn into other classes of organic compounds – amines, cyano and nitro compounds, carbo

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21

François, Benjamin, Ludovic Eberlin, Fabienne Berrée, Andrew Whiting, and Bertrand Carboni. "Access to Fused Pyrroles from Cyclic 1,3-Dienyl Boronic Esters and Arylnitroso Compounds." Journal of Organic Chemistry 85, no. 8 (2020): 5173–82. http://dx.doi.org/10.1021/acs.joc.9b03214.

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22

Yan, Rulong, Xing Kang, Xiaoqiang Zhou та ін. "I2-Catalyzed Synthesis of Substituted Pyrroles from α-Amino Carbonyl Compounds and Aldehydes". Journal of Organic Chemistry 79, № 1 (2013): 465–70. http://dx.doi.org/10.1021/jo402620z.

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23

Arcadi, Antonio, Maria Alfonsi, Gabriele Bianchi, Gaetano D'Anniballe, and Fabio Marinelli. "Gold-Catalysed Direct Couplings of Indoles and Pyrroles with 1,3-Dicarbonyl Compounds." Advanced Synthesis & Catalysis 348, no. 3 (2006): 331–38. http://dx.doi.org/10.1002/adsc.200505345.

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24

Thammarat, Poowadol, Chadin Kulsing, Kanet Wongravee, Natchanun Leepipatpiboon, and Thumnoon Nhujak. "Identification of Volatile Compounds and Selection of Discriminant Markers for Elephant Dung Coffee Using Static Headspace Gas Chromatography—Mass Spectrometry and Chemometrics." Molecules 23, no. 8 (2018): 1910. http://dx.doi.org/10.3390/molecules23081910.

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Elephant dung coffee (Black Ivory Coffee) is a unique Thai coffee produced from Arabica coffee cherries consumed by Asian elephants and collected from their feces. In this work, elephant dung coffee and controls were analyzed using static headspace gas chromatography hyphenated with mass spectrometry (SHS GC-MS), and chemometric approaches were applied for multivariate analysis and the selection of marker compounds that are characteristic of the coffee. Seventy-eight volatile compounds belonging to 13 chemical classes were tentatively identified, including six alcohols, five aldehydes, one car

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25

Bekolo, Henri, and Gilbert Kirsch. "Synthesis of substituted 4-azaisoindoles — New tacrine analogues." Canadian Journal of Chemistry 85, no. 1 (2007): 1–6. http://dx.doi.org/10.1139/v06-180.

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The regioselective Friedländer reaction of 3-amino-4-cyanopyrroles with a series of cyclic ketones has enabled the first reported synthesis of substituted 4-azaisoindoles. Structurally, this new class of compounds stands for the first reported 4-azaisoindole tacrine analogues. A reaction mechanism for the formation of the reported 4-azaisoindoles is proposed.Key words: 4-azaisoindoles, tacrine, Friedländer reaction, pyrroles, mechanism.

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26

Abdelmohsen, Shawkat Ahmed, and Yasser Abou-bakr El-Ossaily. "One-pot synthesis of 5-[1-substituted 4-acetyl-5-methyl-1H-pyrrol-2-yl)]-8-hydroxyquinolines using DABCO as green catalyst." Heterocyclic Communications 21, no. 4 (2015): 207–10. http://dx.doi.org/10.1515/hc-2015-0033.

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AbstractA green and simple method for the synthesis of the title compounds 4 by the reaction of 5-chloroacetyl-8-hydroxyquinoline (1), pentane-2,4-dione (2), and amines 3 in the presence of a catalytic amount of 1,4-diazabicyclo[2.2.2]octane at 60°C is described. The procedure is amenable for the synthesis of other substituted pyrroles. Short reaction time, environmentally friendly procedure, and excellent yields are the main advantages. The structures of products 4a–n were characterized by 1H NMR, IR, and MS spectra.

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27

Tajima, Toshiki, Atsushi Nakajima, and Toshio Fuchigami. "Electrolytic Partial Fluorination of Organic Compounds. 83. Anodic Fluorination ofN-Substituted Pyrroles and Its Synthetic Applications togem-Difluorinated Heterocyclic Compounds." Journal of Organic Chemistry 71, no. 4 (2006): 1436–41. http://dx.doi.org/10.1021/jo0520745.

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28

Bossio, Ricardo, Stefano Marcaccini, and Roberto Pepino. "Studies on Isocyanides and Related Compounds: A Novel Synthesis of Pyrroles via Ugi Reaction." Synthesis 1994, no. 08 (1994): 765–66. http://dx.doi.org/10.1055/s-1994-25565.

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29

Chiba, Shunsuke, Yi-Feng Wang, Guillaume Lapointe, and Koichi Narasaka. "Synthesis of PolysubstitutedN-H Pyrroles from Vinyl Azides and 1,3-Dicarbonyl Compounds." Organic Letters 10, no. 2 (2008): 313–16. http://dx.doi.org/10.1021/ol702727j.

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30

Xiong, Mingteng, Xiao Liang, Yifeng Zhou, and Yuanjiang Pan. "Synthesis of Polysubstituted Pyrroles through Electro-Oxidative Annulation of 1,3-Dicarbonyl Compounds and Primary Amines." Journal of Organic Chemistry 86, no. 7 (2021): 4986–93. http://dx.doi.org/10.1021/acs.joc.0c02911.

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31

González‐Soria, María José, and Francisco Alonso. "Substrate‐Controlled Divergent Synthesis of Enaminones and Pyrroles from Indolizines and Nitroso Compounds." Advanced Synthesis & Catalysis 361, no. 21 (2019): 5005–17. http://dx.doi.org/10.1002/adsc.201900837.

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32

Seo, Jia, Che-Wei Chen, Shih-Ching Chuang, et al. "Palladium-Catalyzed C–H Benzannulation of Functionalized Furans and Pyrroles with Alkynes." Synthesis 53, no. 17 (2021): 3001–10. http://dx.doi.org/10.1055/a-1502-3641.

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AbstractA benzannulation strategy involving activation of two C–H bonds of five-membered heteroarenes was developed. Readily available furans and pyrroles stabilized by synthetically useful electron-withdrawing groups underwent Pd-catalyzed 1:2 annulation reactions with diaryl alkynes. A variety of functional groups, including ester, amide, ketone, aldehyde, and nitrile, on the heterocyclic cores were tolerated in the Pd-catalyzed oxidative reactions. In these reactions, the combination of 2,2-dimethylbutyric acid and its conjugate base facilitated metalation at the heteroaromatic rings and re

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33

Wang, Yi-Feng, Kah Kah Toh, Shunsuke Chiba, and Koichi Narasaka. "Mn(III)-Catalyzed Synthesis of Pyrroles from Vinyl Azides and 1,3-Dicarbonyl Compounds." Organic Letters 10, no. 21 (2008): 5019–22. http://dx.doi.org/10.1021/ol802120u.

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34

Ng, Eileen Pei Jian, Yi-Feng Wang, Benjamin Wei-Qiang Hui, Guillaume Lapointe, and Shunsuke Chiba. "Orthogonal synthesis of pyrroles and 1,2,3-triazoles from vinyl azides and 1,3-dicarbonyl compounds." Tetrahedron 67, no. 40 (2011): 7728–37. http://dx.doi.org/10.1016/j.tet.2011.08.006.

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35

Sar, Saibal, Ranajit Das, Dhiraj Barman, et al. "A sustainable C–H functionalization of indoles, pyrroles and furans under a blue LED with iodonium ylides." Organic & Biomolecular Chemistry 19, no. 35 (2021): 7627–32. http://dx.doi.org/10.1039/d1ob01219c.

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Pyrrole and indole derivatives are functionalized with the dimethyl malonate derived phenyl iodonium ylide in the presence of a blue LED via C–H functionalization of the respective heterocycles in methanol to generate the desired compounds.

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36

Huang, Hao, Christoffer Karlsson, Maria Strømme, Martin Sjödin, and Adolf Gogoll. "Hydroquinone–pyrrole dyads with varied linkers." Beilstein Journal of Organic Chemistry 12 (January 18, 2016): 89–96. http://dx.doi.org/10.3762/bjoc.12.10.

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A series of pyrroles functionalized in the 3-position with p-dimethoxybenzene via various linkers (CH2, CH2CH2, CH=CH, C≡C) has been synthesized. Their electronic properties have been deduced from 1H NMR, 13C NMR, and UV–vis spectra to detect possible interactions between the two aromatic subunits. The extent of conjugation between the subunits is largely controlled by the nature of the linker, with the largest conjugation found with the trans-ethene linker and the weakest with the aliphatic linkers. DFT calculations revealed substantial changes in the HOMO–LUMO gap that correlated with the ex

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37

Demir, Ayhan S., A. Cigdem Igdir, and N. Batuhan Günay. "Amination/annulation of chlorobutenones with chiral amine compounds: synthesis of 1,2,4-trisubstituted pyrroles." Tetrahedron: Asymmetry 16, no. 19 (2005): 3170–75. http://dx.doi.org/10.1016/j.tetasy.2005.08.033.

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38

Starowicz, Małgorzata, Georgios Koutsidis та Henryk Zieliński. "Determination of Antioxidant Capacity, Phenolics and Volatile Maillard Reaction Products in Rye-Buckwheat Biscuits Supplemented with 3β-d-Rutinoside". Molecules 24, № 5 (2019): 982. http://dx.doi.org/10.3390/molecules24050982.

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The Maillard reaction (MR) is responsible for the development of color, taste and aroma in bakery products though the formation of numerous aroma compounds such as pyrazines, pyrroles and aldehydes, nonvolatile taste active compounds and melanoidins. In this article, we investigate the effect of quercetin 3β-D-rutinoside (rutin) supplementation, at the level of 5–50 mg per 100 g, of rye-buckwheat biscuits on the formation of phenolics and volatile Maillard reaction products (MRPs) such as pyrazines, furfuryl alcohol and furfural, determined by headspace solid phase microextraction followed by

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39

Yadav, J. S., B. V. S. Reddy та G. Satheesh. "InBr3/Cu(OTf)2-catalyzed C-alkylation of pyrroles and indoles with α-diazocarbonyl compounds". Tetrahedron Letters 44, № 45 (2003): 8331–34. http://dx.doi.org/10.1016/j.tetlet.2003.09.031.

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40

Tan, Wei Wen, and Naohiko Yoshikai. "Copper-Catalyzed Coupling of 2-Siloxy-1-alkenes and Diazocarbonyl Compounds: Approach to Multisubstituted Furans, Pyrroles, and Thiophenes." Journal of Organic Chemistry 81, no. 13 (2016): 5566–73. http://dx.doi.org/10.1021/acs.joc.6b00904.

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41

Grela, Karol, Syed Shafi та Mariusz Kędziorek. "Cross Metathesis of N-Allylamines and α,β-Unsaturated Carbonyl Compounds: A One-Pot Synthesis of Substituted Pyrroles". Synlett 2011, № 01 (2010): 124–28. http://dx.doi.org/10.1055/s-0030-1259083.

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Rybalkin, Vladimir P., Sofiya Yu Zmeeva, Lidiya L. Popova, et al. "Synthesis and highly efficient light-induced rearrangements of diphenylmethylene(2-benzo[b]thienyl)fulgides and fulgimides." Beilstein Journal of Organic Chemistry 16 (July 22, 2020): 1820–29. http://dx.doi.org/10.3762/bjoc.16.149.

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2-Benzo[b]thienyl fulgides and fulgimides containing bulky diphenylmethylene substituents were synthesized in the form of their ring-opened E- or Z-isomers. In contrast to the majority of known fulgides/fulgimides, that form colored ring-closed structures under UV irradiation, the obtained compounds undergo an irreversible transformation leading to decoloration of their solutions. This rearrangement with the formation of the dihydronaphthalene core appeared to be by 2–3 orders of magnitude more efficient than for the known diphenylmethylene(aryl(hetaryl))fulgides. The molecular structures of E

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Fu, Jiantao, Nikolai Wurzer, Verena Lehner, Oliver Reiser, and Huw M. L. Davies. "Rh(II)-Catalyzed Monocyclopropanation of Pyrroles and Its Application to the Synthesis Pharmaceutically Relevant Compounds." Organic Letters 21, no. 15 (2019): 6102–6. http://dx.doi.org/10.1021/acs.orglett.9b02250.

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Nomiyama, Shota, Takahiro Ogura, Hiroaki Ishida, Kazuki Aoki та Teruhisa Tsuchimoto. "Indium-Catalyzed Regioselective β-Alkylation of Pyrroles with Carbonyl Compounds and Hydrosilanes and Its Application to Construction of a Quaternary Carbon Center with a β-Pyrrolyl Group". Journal of Organic Chemistry 82, № 10 (2017): 5178–97. http://dx.doi.org/10.1021/acs.joc.7b00446.

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Steinert, Henning, Christopher Schwarz, Alexander Kroll, and Viktoria H. Gessner. "Towards the Preparation of Stable Cyclic Amino(ylide)Carbenes." Molecules 25, no. 4 (2020): 796. http://dx.doi.org/10.3390/molecules25040796.

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Cyclic amino(ylide)carbenes (CAYCs) are the ylide-substituted analogues of N-heterocyclic Carbenes (NHCs). Due to the stronger π donation of the ylide compared to an amino moiety they are stronger donors and thus are desirable ligands for catalysis. However, no stable CAYC has been reported until today. Here, we describe experimental and computational studies on the synthesis and stability of CAYCs based on pyrroles with trialkyl onium groups. Attempts to isolate two CAYCs with trialkyl phosphonium and sulfonium ylides resulted in the deprotonation of the alkyl groups instead of the formation

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Bray, Brian L., та Joseph M. Muchowski. "α-(Dialkylamino)-α-pyrrolylacetonitriles. A potpourri of useful synthetic transformations". Canadian Journal of Chemistry 68, № 8 (1990): 1305–8. http://dx.doi.org/10.1139/v90-201.

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α-(Dialkylamino)-α-(pyrrol-2-yl)acetonitriles (3) are versatile intermediates that are readily converted into regiochemically pure 2-bromo-6-dialkylamino-1-azafulvenes and 5-bromo-2-acylpyrroles (acyl = CHO, COR). In addition, 3 (R1 = H), 4 (R1 = H), and the β-substituted compound 9 are transformed easily and under mild conditions, via the corresponding α-methylthio compounds (e.g., 7a), into the methyl pyrrole carboxylates 8a, 8b, and 10, respectively. Keywords: α-(dialkylamino)-α-(pyrrol-2-yl)acetonitriles, 5-bromo-2-acylpyrroles, methyl pyrrole carboxylates.

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Zhao, Mi-Na, Gui-Wan Ning, De-Suo Yang, Peng Gao, Ming-Jin Fan, and Li-Fang Zhao. "Nickel-catalyzed formal [3 + 2]-cycloaddition of 2H-azirines with 1,3-dicarbonyl compounds for the synthesis of pyrroles." Tetrahedron Letters 61, no. 38 (2020): 152319. http://dx.doi.org/10.1016/j.tetlet.2020.152319.

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TAJIMA, Toshiki, Atsushi NAKAJIMA, and Toshio FUCHIGAMI. "Electrochemical Partial Fluorination of Organic Compounds (76). Selective Anodic Fluorination of N-Protected Pyrroles Towards Environmentally Friendly Process." Electrochemistry 72, no. 12 (2004): 843–45. http://dx.doi.org/10.5796/electrochemistry.72.843.

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Escobar, Angélica M., Guillermo Blustein, Rafael Luque, and Gustavo P. Romanelli. "Recent Applications of Heteropolyacids and Related Compounds in Heterocycle Synthesis. Contributions between 2010 and 2020." Catalysts 11, no. 2 (2021): 291. http://dx.doi.org/10.3390/catal11020291.

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Over the past two decades, polyoxometalates (POM) have received considerable attention as solid catalysts, due to their unique physicochemical characteristics, since, first, they have very strong Bronsted acidity, approaching the region of a superacid, and second, they are efficient oxidizers that exhibit rapid redox transformations under fairly mild conditions. Their structural mobility is also highlighted, since they are complex molecules that can be modified by changing their structure or the elements that compose them to model their size, charge density, redox potentials, acidity, and solu

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Wei, Hao-Zhao, Liu-Zhu Yu, and Min Shi. "Lewis or Brønsted acid-catalysed reaction of propargylic alcohol-tethered alkylidenecyclopropanes with indoles and pyrroles for the preparation of polycyclic compounds tethered with indole or pyrrole motif." Organic & Biomolecular Chemistry 18, no. 1 (2020): 135–39. http://dx.doi.org/10.1039/c9ob02211b.

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We developed a facile synthetic method to access the cyclopenta[b]naphthalene skeleton from Lewis or Brønsted acid-catalysed propargylic alcohol-tethered alkylidenecyclopropanes with indole and pyrrole derivatives.

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