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Journal articles on the topic 'Paal-Knorr'

Author: Grafiati

Published: 4 June 2021

Last updated: 26 July 2025

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1

Abbat, Sheenu, Devendra Dhaked, Minhajul Arfeen, and Prasad V. Bharatam. "Mechanism of the Paal–Knorr reaction: the importance of water mediated hemialcohol pathway." RSC Advances 5, no. 107 (2015): 88353–66. http://dx.doi.org/10.1039/c5ra16246g.

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The mechanism of the Paal–Knorr reaction was explored using quantum chemical methods. Hydronium ion catalysed hemialcohol pathway has been established as the preferred mechanistic route for the Paal–Knorr formation of furan, pyrrole and thiophene.

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2

Wagh, Sachin B., Vladimir Maslivetc, James J. La Clair, and Alexander Kornienko. "A fluorescent target-guided Paal–Knorr reaction." RSC Advances 10, no. 61 (2020): 37035–39. http://dx.doi.org/10.1039/d0ra06962k.

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3

Truong Nguyen, Hai, Duy-Khiem Nguyen Chau, and Phuong Hoang Tran. "A green and efficient method for the synthesis of pyrroles using a deep eutectic solvent ([CholineCl][ZnCl2]3) under solvent-free sonication." New J. Chem. 41, no. 21 (2017): 12481–89. http://dx.doi.org/10.1039/c7nj02396k.

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4

Akbaşlar, Dilek, Onur Demirkol, and Sultan Giray. "Paal–Knorr Pyrrole Synthesis in Water." Synthetic Communications 44, no. 9 (2014): 1323–32. http://dx.doi.org/10.1080/00397911.2013.857691.

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5

Mou, Xue-Qing, Zheng-Liang Xu, Shao-Hua Wang, et al. "An Au(i)-catalyzed rearrangement/cyclization cascade toward the synthesis of 2-substituted-1,4,5,6-tetrahydrocyclopenta[b]pyrrole." Chemical Communications 51, no. 60 (2015): 12064–67. http://dx.doi.org/10.1039/c5cc03979g.

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6

Wang, Min-Ran, Jing-Yang He, Ji-Xiang He, Ke-Ke Liu, and Jing Yang. "A Paal–Knorr agent for chemoproteomic profiling of targets of isoketals in cells." Chemical Science 12, no. 43 (2021): 14557–63. http://dx.doi.org/10.1039/d1sc02230j.

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7

Alvi, Shakeel, and Rashid Ali. "An expeditious and highly efficient synthesis of substituted pyrroles using a low melting deep eutectic mixture." Organic & Biomolecular Chemistry 19, no. 44 (2021): 9732–45. http://dx.doi.org/10.1039/d1ob01618k.

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8

Menuel, S., E. Bertaut, E. Monflier, and F. Hapiot. "Cyclodextrin-based PNN supramolecular assemblies: a new class of pincer-type ligands for aqueous organometallic catalysis." Dalton Transactions 44, no. 30 (2015): 13504–12. http://dx.doi.org/10.1039/c5dt01825k.

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9

Kornienko, Alexander, and James J. La Clair. "Covalent modification of biological targets with natural products through Paal–Knorr pyrrole formation." Natural Product Reports 34, no. 9 (2017): 1051–60. http://dx.doi.org/10.1039/c7np00024c.

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10

Mateev, Emilio, Ali Irfan, Alexandrina Mateeva, Maya Georgieva, and Alexander Zlatkov. "Microwave-assisted organic synthesis of pyrroles (Review)." Pharmacia 71 (March 25, 2024): 1–10. http://dx.doi.org/10.3897/pharmacia.71.e119866.

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The detection of pyrrole rings in numerous organic compounds with various pharmacological activities, emphasizes its huge importance in medicinal chemistry. Thus, the synthesis of pyrroles continues to arouse interest and Paal-Knorr condensation is considered to be the main synthetic route. A significant advance has been made since the MW activation was introduced in the organic synthesis which can be confirmed with the rapid growth of the published papers on that topic. Microwave irradiation is gaining popularity since faster reaction time, higher yields, easier work-up and reduced energy inp

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11

Mateev, Emilio, Ali Irfan, Alexandrina Mateeva, Maya Georgieva, and Alexander Zlatkov. "Microwave-assisted organic synthesis of pyrroles (Review)." Pharmacia 71, no. () (2024): 1–10. https://doi.org/10.3897/pharmacia.71.e119866.

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The detection of pyrrole rings in numerous organic compounds with various pharmacological activities, emphasizes its huge importance in medicinal chemistry. Thus, the synthesis of pyrroles continues to arouse interest and Paal-Knorr condensation is considered to be the main synthetic route. A significant advance has been made since the MW activation was introduced in the organic synthesis which can be confirmed with the rapid growth of the published papers on that topic. Microwave irradiation is gaining popularity since faster reaction time, higher yields, easier work-up and reduced energy inp

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12

Mulzer, Johann, and Anna Innitzer. "A Tetracarbonyl Paal-Knorr Approach to Semicorrins." HETEROCYCLES 77, no. 2 (2009): 873. http://dx.doi.org/10.3987/com-08-s(f)54.

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13

Dasari, Ramesh, James J. La Clair, and Alexander Kornienko. "Irreversible Protein Labeling by Paal-Knorr Conjugation." ChemBioChem 18, no. 18 (2017): 1792–96. http://dx.doi.org/10.1002/cbic.201700210.

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14

Rajeshkumar, Venkatachalam, Chinnaraj Neelamegam, and Sambandam Anandan. "A one-pot metal-free protocol for the synthesis of chalcogenated furans from 1,4-enediones and thiols." Organic & Biomolecular Chemistry 17, no. 4 (2019): 982–91. http://dx.doi.org/10.1039/c8ob03051k.

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Transition-metal-free synthesis of chalcogenated furans through the sequential thiol-Michael/Paal–Knorr reaction of 1,4-enediones in the presence of a catalytic amount of p-toluene sulfonic acid has been developed.

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15

Amarnath, Venkataraman, and Kalyani Amarnath. "Intermediates in the Paal-Knorr Synthesis of Furans." Journal of Organic Chemistry 60, no. 2 (1995): 301–7. http://dx.doi.org/10.1021/jo00107a006.

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16

Amarnath, Venkataraman, Douglas C. Anthony, Kalyani Amarnath, William M. Valentine, Lawrence A. Wetterau, and Doyle G. Graham. "Intermediates in the Paal-Knorr synthesis of pyrroles." Journal of Organic Chemistry 56, no. 24 (1991): 6924–31. http://dx.doi.org/10.1021/jo00024a040.

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17

Akbaslar, Dilek, Onur Demirkol, and Sultan Giray. "ChemInform Abstract: Paal-Knorr Pyrrole Synthesis in Water." ChemInform 45, no. 38 (2014): no. http://dx.doi.org/10.1002/chin.201438109.

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18

Akelis, Liudvikas, Jolanta Rousseau, Robertas Juskenas, et al. "Greener Paal-Knorr Pyrrole Synthesis by Mechanical Activation." European Journal of Organic Chemistry 2016, no. 1 (2015): 31–35. http://dx.doi.org/10.1002/ejoc.201501223.

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19

Sherikar, Mahadev Sharanappa, Kiran R. Bettadapur, Veeranjaneyulu Lanke, and Kandikere Ramaiah Prabhu. "Rhodium(iii)-catalyzed synthesis of trisubstituted furans via vinylic C–H bond activation." Organic & Biomolecular Chemistry 19, no. 34 (2021): 7470–74. http://dx.doi.org/10.1039/d1ob01293b.

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A simple method for the synthesis of trisubstituted furans has been disclosed using an Rh(iii)-catalyst by Cvinyl–H bond activation, with silver salt Ag(i) is playing a dual role – a halide scavenger and a Lewis acid catalyst for promoting Paal–Knorr type cyclization.

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20

Handy, Scott, and Kevin Lavender. "Organic synthesis in deep eutectic solvents: Paal–Knorr reactions." Tetrahedron Letters 54, no. 33 (2013): 4377–79. http://dx.doi.org/10.1016/j.tetlet.2013.05.122.

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21

Banik, Bimal K., Indrani Banik, Mercy Renteria, and Swapan K. Dasgupta. "A straightforward highly efficient Paal–Knorr synthesis of pyrroles." Tetrahedron Letters 46, no. 15 (2005): 2643–45. http://dx.doi.org/10.1016/j.tetlet.2005.02.103.

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22

Zard, Samir Z., Béatrice Quiclet-Sire, Leticia Quintero, and Graciela Sanchez-Jimenez. "A Practical Variation on the Paal-Knorr Pyrrole Synthesis." Synlett, no. 1 (2002): 0075–78. http://dx.doi.org/10.1055/s-2003-36223.

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23

Szakal-Quin, Gyongyi, Doyle G. Graham, David S. Millington, David A. Maltby, and Andrew T. McPhail. "Stereoisomer effects on the Paal-Knorr synthesis of pyrroles." Journal of Organic Chemistry 51, no. 5 (1986): 621–24. http://dx.doi.org/10.1021/jo00355a010.

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24

Kidwai, Mazaahir, Kavita Singhal, and Shweta Rastogi. "Paal knorr reaction for novel pyrrolo[2,3-d]pyrimidines." Journal of Heterocyclic Chemistry 43, no. 5 (2006): 1231–36. http://dx.doi.org/10.1002/jhet.5570430514.

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25

Jiang, Xia, Hui Jin, Tingshu Wang, Hyebin Yoo, and Sangho Koo. "Synthesis of Phenyl-2,2′-bichalcophenes and Their Aza-Analogues by Catalytic Oxidative Deacetylation." Synthesis 51, no. 17 (2019): 3259–68. http://dx.doi.org/10.1055/s-0037-1611564.

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Efficient synthetic method for medicinally and opto-electronically important bichalcophenes is reported, which highlights Mn(OAc)3/CoCl2-catalyzed oxidative deacetylation of 1,5-dicarbonyl compounds that were easily prepared by conjugate addition of ethyl acetoacetate to α,β-unsaturated carbonyl compounds containing a chalcophene unit. Paal–Knorr reaction of the resulting 1,4-dicarbonyl compounds produced 4-phenyl-2,2′-bichalcophenes and their aza-analogues.

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26

Amarnath, Venkataraman, Kalyani Amarnath, William M. Valentine, Michael A. Eng, and Doyle G. Graham. "Intermediates in the Paal-Knorr Synthesis of Pyrroles. 4-Oxoaldehydes." Chemical Research in Toxicology 8, no. 2 (1995): 234–38. http://dx.doi.org/10.1021/tx00044a008.

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27

Lapina, I. M., L. M. Pevzner, and A. A. Potekhin. "Aminomethyl derivatives of furancarboxylic acids in the Paal-Knorr reaction." Russian Journal of General Chemistry 77, no. 5 (2007): 923–25. http://dx.doi.org/10.1134/s1070363207050180.

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28

Balakrishna, Avula, António Aguiar, Pedro J. M. Sobral, Mohmmad Younus Wani, Joana Almeida e Silva, and Abilio J. F. N. Sobral. "Paal–Knorr synthesis of pyrroles: from conventional to green synthesis." Catalysis Reviews 61, no. 1 (2018): 84–110. http://dx.doi.org/10.1080/01614940.2018.1529932.

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29

Dittrich, Nora, Eun-Kyung Jung, Samuel J. Davidson, and David Barker. "An acyl-Claisen/Paal-Knorr approach to fully substituted pyrroles." Tetrahedron 72, no. 31 (2016): 4676–89. http://dx.doi.org/10.1016/j.tet.2016.06.049.

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30

Ryzhkov, I. O., I. A. Andreev, G. M. Belov, A. V. Kurkin, and M. A. Yurovskaya. "Preparation of chiral pyrrole derivatives by the Paal-Knorr reaction." Chemistry of Heterocyclic Compounds 47, no. 2 (2011): 182–93. http://dx.doi.org/10.1007/s10593-011-0739-7.

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31

Banik, Mandira, Bianca Ramirez, Ashwini Reddy, Debasish Bandyopadhyay, and Bimal K. Banik. "Polystyrenesulfonate-catalyzed synthesis of novel pyrroles through Paal-Knorr reaction." Organic and Medicinal Chemistry Letters 2, no. 1 (2012): 11. http://dx.doi.org/10.1186/2191-2858-2-11.

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32

Pasha, Sk Khadeer, V. S. V. Satyanarayana, A. Sivakumar, K. Chidambaram та L. John Kennedy. "Catalytic applications of nano β-PbO in Paal–Knorr reaction". Chinese Chemical Letters 22, № 8 (2011): 891–94. http://dx.doi.org/10.1016/j.cclet.2010.12.053.

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33

王, 廷敏. "Knorr-Paal逆反应机制的研究". Chinese Journal of Applied Chemistry 3, № 2 (1986): 84. http://dx.doi.org/10.3724/j.issn.1000-0518.1986.2.8484.

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34

Sugita, Kazuyuki, Rintaro Matsuo, Ayumu Miyashita, Motoi Kuwabara, Shinya Adachi, and Akinobu Matsuzawa. "Concise Diastereoselective Total Synthesis of (±)-Parvistemonine A." Synlett 31, no. 18 (2020): 1800–1804. http://dx.doi.org/10.1055/s-0040-1707283.

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AbstractWe have developed a concise diastereoselective total synthesis of (±)-parvistemonine A. By using a Mukaiyama–Michael addition, an aza-Wittig reaction, a Paal–Knorr pyrrole synthesis, an acid-mediated annulation, and a Mitsunobu reaction as key steps, we achieved a total synthesis in which the longest linear sequence was ten steps and the overall yield was 19.6%. Additionally, the relative stereochemistry of parvistemonine A was confirmed by X-ray crystallographic analysis for the first time.

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35

He, Yan-Hong, Gang-Qiang Wang, Ke-Ling Xu, and Zhi Guan. "An Efficient Procedure for the Synthesis of Polysubstituted Pyrroles in an Ionic Liquid." Zeitschrift für Naturforschung B 66, no. 2 (2011): 191–96. http://dx.doi.org/10.1515/znb-2011-0212.

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The ionic liquid 1-butyl-3-methyl-imidazolium hydrogen sulfate, [bmim]HSO4, was used as a catalyst and reaction medium for the pyrrole synthesis, and a wide range of aliphatic, aromatic, heteroaromatic and carboxylic 1,4-diketones easily underwent condensations with aniline and ethylenediamine to form polysubstituted pyrroles. Sequential decarboxylation/Paal-Knorr pyrrole condensation was observed, which provides a new and facile approach to monoester pyrroles from 1,4-diketo-2,3-dicarboxylic acid esters.

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36

Aghapoor, Kioumars, Mostafa M. Amini, Khosrow Jadidi, Farshid Mohsenzadeh, and Hossein Reza Darabi. "Catalytic activity of the nanoporous MCM-41 surface for the Paal–Knorr pyrrole cyclocondensation." Zeitschrift für Naturforschung B 70, no. 7 (2015): 475–81. http://dx.doi.org/10.1515/znb-2014-0259.

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AbstractThe investigation of different oxide surfaces revealed that nanoporous silica (MCM-41) had the best catalytic activity for Paal–Knorr pyrrole synthesis. Despite the same composition, MCM-41 proved to be more effective than SiO2 itself, probably due to a significantly higher surface area of the SiO2 nanopores. The important features of this “clean” solvent-free protocol are the ease of recovery and the reuse of the catalyst for several cycles, operational simplicity, and easy product isolation and purification.

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37

Mahato, Sanjit K., Jayaraman Vinayagam, Sumit Dey, Ajay K. Timiri, Sourav Chatterjee, and Parasuraman Jaisankar. "InCl3 Catalysed One-Pot Synthesis of Substituted Pyrroles and 2-Pyrones." Australian Journal of Chemistry 66, no. 2 (2013): 241. http://dx.doi.org/10.1071/ch12359.

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An efficient InCl3 catalysed one-pot strategy has been developed for the synthesis of tetra-substituted pyrroles and tri-substituted 2-pyrones in very good yields. Tetra-substituted pyrroles were prepared from 1,4-enediones and β-dicarbonyls employing NH4OAc as a nitrogen source, through a combination of Michael addition and Paal–Knorr methods. Tri-substituted 2-pyrones were synthesised from 1,4-ynediones and appropriate β-dicarbonyls using a sequential Michael addition and 6-exo-trig cyclisation.

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38

Portilla-Zúñiga, Omar, Ángel Sathicq, José Martínez, et al. "Novel Bifunctional Mesoporous Catalysts Based on Preyssler Heteropolyacids for Green Pyrrole Derivative Synthesis." Catalysts 8, no. 10 (2018): 419. http://dx.doi.org/10.3390/catal8100419.

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In this paper, we report the synthesis of Preyssler heteropolyacids supported on mesoporous alumina in order to obtain materials with acid–base properties. A series of pyrrole derivatives were synthesized using a suitable procedure under solvent-free conditions. Using the alumina-supported material, more complex pyrrole derivatives can be obtained through a tandem one-pot process that involves the formation of 2-amino-3-cyano 4-H-chromenes by a multicomponent reaction and their subsequent conversion to pyrrole using a Paal–Knorr reaction.

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39

Obruchnikova, Natalia V., and Oleg A. Rakitin. "4-(2,5-Dimethyl-1H-pyrrol-1-yl)-1,2,5-oxadiazol-3-amine." Molbank 2023, no. 3 (2023): M1700. http://dx.doi.org/10.3390/m1700.

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1,2,5-Oxadiazol-3-amines with a heterocyclic substituent in the 4-position are being intensively investigated as compounds with valuable pharmacological activity. In this communication, the reaction of 1,2,5-oxadiazole-3,4-diamine with 2,5-hexanedione was shown to selectively give 4-(2,5-dimethyl-1H-pyrrol-1-yl)-1,2,5-oxadiazol-3-amine as a product of the Paal–Knorr reaction. The structure of the synthesized compound was established by elemental analysis, high-resolution mass spectrometry, 1H and 13C NMR, and IR spectroscopy.

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40

Sonal N, Doltade, Dr Malpani Suraj, Siral Vaishnavi, Khandekar Jnardan, Bhakare Mahesh, and Kolekar Mahesh. "Synthesis of thiophene and Their Pharmacological Activity." International Journal of Pharmaceutical Research and Applications 10, no. 2 (2025): 871–75. https://doi.org/10.35629/4494-1002871875.

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Thiophene is a five-membered heterocyclic compound, has garnered significant attention in pharmaceutical research due to its diverse pharmacological activities . This review focuses on the effective thiophene synthesis techniques, such as Fishwicksynthesis, Gewald synthesis, and the microwave-assisted Paal-Knorr reaction. Strong biological actions, including antibacterial, antiinflammatory, anticancer, and effects on the central nervous system (CNS), are exhibited by the produced thiophene derivatives. Particularly, thiophene-based substances have demonstrated promise in the treatment of anxie

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41

Anis Ahmed Sheikh, Ummul Khair Asema, and Abdul Ahad. "Plant Juice Catalysed Synthesis of Substituted Pyrrole through Paal Knorr Reaction." International Journal of Scientific Research in Science, Engineering and Technology 11, no. 5 (2024): 53–56. http://dx.doi.org/10.32628/ijsrset2411586.

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The current research work proposed the novel methodology for the synthesis of N-substituted pyrrole catalysed by juice of Kalanchoe Pinnata plant leaves. The reaction was carried out between hexan 2,5 dione and aniline. This protocol is environmentally benign cost effective and fruitful which has produced the desired product in short reaction time and easy work up. The synthesised compounds has been confirmed by 1HNMR , IR and C13 spectroscopy. The natural abundance, cost effective, non toxic and good to excellent yields are some specific features of this catalyst.

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42

Zhang, Lei, Jian Zhang, Ji Ma, Dao-Juan Cheng, and Bin Tan. "Highly Atroposelective Synthesis of Arylpyrroles by Catalytic Asymmetric Paal–Knorr Reaction." Journal of the American Chemical Society 139, no. 5 (2017): 1714–17. http://dx.doi.org/10.1021/jacs.6b09634.

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43

Kostyanovsky, Remir G., Gulnara K. Kadorkina, Anait G. Mkhitaryan, Ivan I. Chervin, and Abil E. Aliev. "New Scope and Limitations in the Knorr–Paal Synthesis of Pyrroles." Mendeleev Communications 3, no. 1 (1993): 21–23. http://dx.doi.org/10.1070/mc1993v003n01abeh000204.

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44

Handy, Scott, and Kevin Lavender. "ChemInform Abstract: Organic Synthesis in Deep Eutectic Solvents: Paal-Knorr Reactions." ChemInform 44, no. 47 (2013): no. http://dx.doi.org/10.1002/chin.201347090.

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45

Khaghaninejad, Soheila, and Majid M. Heravi. "ChemInform Abstract: Paal-Knorr Reaction in the Synthesis of Heterocyclic Compounds." ChemInform 45, no. 38 (2014): no. http://dx.doi.org/10.1002/chin.201438261.

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46

Shcherbakov, Roman O., Diana A. Eshmemet’eva, Anton A. Merkushev, Igor V. Trushkov, and Maxim G. Uchuskin. "Transformation of 3-(Furan-2-yl)-1,3-di(het)arylpropan-1-ones to Prop-2-en-1-ones via Oxidative Furan Dearomatization/2-Ene-1,4,7-triones Cyclization." Molecules 26, no. 9 (2021): 2637. http://dx.doi.org/10.3390/molecules26092637.

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The approach to 3-(furan-2-yl)-1,3-di(het)arylprop-2-en-1-ones based on the oxidative dearomatization of 3-(furan-2-yl)-1,3-di(het)arylpropan-1-ones followed by an unusual cyclization of the formed di(het)aryl-substituted 2-ene-1,4,7-triones has been developed. The cyclization step is related to the Paal–Knorr synthesis, but the furan ring formation is accompanied in this case by a formal shift of the double bond through the formation of a fully conjugated 4,7-hydroxy-2,4,6-trien-1-one system or its surrogate.

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47

Rajeshkumar, Venkatachalam, Chinnaraj Neelamegam, and Sambandam Anandan. "An Expedient, Direct, Three-Component Approach for the Synthesis of 4-Thioarylpyrroles." Synthesis 51, no. 21 (2019): 4023–33. http://dx.doi.org/10.1055/s-0039-1690024.

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A three-component strategy for the synthesis of 4-thioarylpyrroles from 1,4-enediones, thiols, and ammonium formate in one-pot has been developed. The reaction proceeds through the sequential thiol-Michael/Paal–Knorr reaction of 1,4-enediones with the formation of one new C–S and two C–N bonds. The operationally simple protocol provides direct access to the highly functionalized 4-thioarylpyrroles with free-NH in good to excellent yields. The synthetic application of resulting 4-thioarylpyrroles was demonstrated by oxidation of the sulfur atom to the corresponding sulfoxide and sulfone.

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48

Quiclet-Sire, Béatrice, and Samir Zard. "Convergent Routes to Pyrroles Exploiting the Unusual Radical Chemistry of Xanthates – An Overview." Synlett 28, no. 20 (2017): 2685–96. http://dx.doi.org/10.1055/s-0036-1590809.

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Convergent routes to a variety of pyrroles involving radical additions of xanthates are described. Emphasis is placed on reactions leading to the formation of 1,4-diketones or 1,4-ketoaldehydes or their synthetic equivalents, which can then be condensed with ammonia or primary amines in a variation of the classical Paal–Knorr synthesis of pyrroles. The modification of pyrroles by direct radical addition is also discussed.1 Introduction2 Earlier Routes to Pyrroles3 The Xanthate Radical Addition–Transfer Process4 Application to Pyrrole Synthesis5 Further Variations6 Direct Modification of Existi

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49

Wang, Dao-Lin, Lu Zhang, Jin-Juan Xing, and Lin Liu. "Facile Synthesis of (Guaiazulen-1-yl)-1H-pyrroles via Paal-Knorr Reaction." HETEROCYCLES 98, no. 11 (2019): 1555. http://dx.doi.org/10.3987/com-19-14166.

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50

Wang, Bo, Yanlong Gu, Cheng Luo, Tao Yang, Liming Yang, and Jishuan Suo. "Pyrrole synthesis in ionic liquids by Paal–Knorr condensation under mild conditions." Tetrahedron Letters 45, no. 17 (2004): 3417–19. http://dx.doi.org/10.1016/j.tetlet.2004.03.012.

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