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Journal articles on the topic 'Perkin reaction and Pechmann reaction'

Author: Grafiati

Published: 3 June 2025

Last updated: 31 July 2025

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1

G.Nagaraju1, *. Dr.Vijaya Kuchana. "A REVIEW ON BIOLOGICAL ACTIVITY AND SYNTHETIS OF COUMARINS." Indo American Journal of Pharmaceutical Sciences 04, no. 10 (2017): 3510–27. https://doi.org/10.5281/zenodo.1004361.

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Coumarin (1,2-Benzopyrone or 2H-1-benzopyran-2-one, or phenylpropanoids, 1) and its derivatives (coumarins) are widely distributed throughout nature and many exhibit useful and diverse biological activities1,2. Coumarins occur as secondary metabolites in the seeds, roots and leaves of many plant species, notably in high concentration in the tonka bean and thus the name comes from a French word, coumarou, for the tonka bean. Their function is far from clear, although suggestions include plant growth regulations, fungistasis, bacteriostasis and, even, waste products3 . Some naturally occurring c

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2

Jumal, Juliana, and Norhanis Sakinah. "Synthesis, Characterization, and Applications of Coumarin Derivatives: A Short Review." Malaysian Journal of Science Health & Technology 7, no. 1 (2021): 62–68. http://dx.doi.org/10.33102/mjosht.v7i1.145.

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Coumarin and its derivatives represent one of the most active curriculums of compound possessing a broad spectrum of biological activity along with other applications such as insecticide and fragrance. There are various methodologies developed for the synthesis of coumarins. Classical routes to coumarins include Pechmann condensation, Knoevenagel condensation, Perkin reaction, and Wittig condensation reactions. Researchers have carried out adjustments and improvements to increase the efficacy and overcome the limitations from the classical route. In this review outline, coumarin derivatives we

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3

Nagaretnam, Prahadeesh, and Sithambaresan Maheswaran. "Synthesis of Simple Coumarins: Mixed Solvent Recrystallization Approach and Modification." RESEARCH REVIEW International Journal of Multidisciplinary 4, no. 1 (2019): 455–61. https://doi.org/10.5281/zenodo.2548800.

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Coumarin compounds have great interest for their wide range of medicinal and pharmacological properties as well as for their fluorescent properties. Simple coumarins are being the major precursor for the synthesis of most of the coumarin derivatives. Simple coumarin (C1) was synthesized by using Perkin condensation reaction whereas 7-hydroxy coumarin (C2) and 7-hydroxy-4-methyl coumarin (C3) were synthesized by using Pechmann condensation reaction. Solvent combination which gives higher recovery percentage on recrystallization was found out. The synthesized simple coumarins were characterized

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4

Gouda, Moustafa A., Mohammed A. Salem, and Mohamed H. Helal. "A Review on Synthesis and Pharmacological Activity of Coumarins and Their Analogs." Current Bioactive Compounds 16, no. 6 (2020): 818–36. http://dx.doi.org/10.2174/1573407215666190405154406.

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Background: Coumarins were reported to possess antimicrobial, antiinflammatory, antiplasmodial, antimalarial, and enzyme inhibitory properties. Furthermore, coumarins are a type of vitamin K antagonists. Coumarins had been first organized through perkin reaction; besides Knoevenagel condensation was mentioned as a critical synthetic approach for the synthesis of 3-substituted coumarins. Moreover, Pechmann, Reformatasky and Witting reactions were stated for the preparation of coumarins. Methods: We undertook a structured search of the method of preparation, the chemical reactivity and biologica

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5

Molnar, Maja, Melita Lončarić, and Marija Kovač. "Green Chemistry Approaches to the Synthesis of Coumarin Derivatives." Current Organic Chemistry 24, no. 1 (2020): 4–43. http://dx.doi.org/10.2174/1385272824666200120144305.

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This review is a compilation of the green synthetic methods used in the synthesis of coumarin derivatives. Coumarins are a class of compounds with a pronounced wide range of biological activities, which have found their application in medicine, pharmacology, cosmetics and food industry. Their biological activity and potential application are highly dependent on their structure. Therefore, many researchers have been performing the synthesis of coumarin derivatives on a daily basis. High demands for their synthesis often result in an increased generation of different waste chemicals. In order to

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6

Holden, Michael S., and R. David Crouch. "The Pechmann Reaction." Journal of Chemical Education 75, no. 12 (1998): 1631. http://dx.doi.org/10.1021/ed075p1631.

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7

Francisco, Carla S., Cristina S. Francisco, André F. Constantino, Álvaro Cunha Neto, and Valdemar Lacerda. "Synthetic Methods Applied in the Preparation of Coumarin-based Compounds." Current Organic Chemistry 23, no. 24 (2020): 2722–50. http://dx.doi.org/10.2174/1385272823666191121150047.

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Coumarins (2H-chromen-2-ones) are heterocyclic compounds of wide scientific interest due to their important biological and pharmaceutical properties such as antitumor, antioxidant, anti-inflammatory and antimicrobial activities as well as enzymatic inhibitors related to neurodegenerative diseases. Due to their structural variability, this compound class has been attracting considerable interest in the natural products and synthetic organic chemistry areas. Coumarins and their derivatives have been prepared by a variety of methods, including Perkin, Wittig and Reformatsky reactions, Pechmann an

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8

Gurumeet, C. Wadhawa 1. *. Harshada Deshmukh 2. Vitthal S. Shivankar 3. Yashwant A. Gaikwad 4. "ONE-POT SYNTHESIS OF THE COUMARINE UNDER GREEN APPROACH USING FERROUS SULPHATE AS CATALYST." Journal of Pharma Research 8, no. 4 (2019): 132–35. https://doi.org/10.5281/zenodo.2647854.

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<strong><em>ABSTRACT</em></strong> <strong><em>S</em></strong><em>ynthesis of various substituted Coumarins from substituted phenol and β-ketoester (Ethyl Acetoacetate) via Pechmann condensation using heterogeneous catalyst like red mud solvent free condition under sonication. Reaction required low reaction time, very mild reaction condition, at room temperature and easy workup with good yield of the product.</em> <strong><em>KEYWORDS:</em></strong><em> Coumarins, Pechmann condensation, Solvent free reaction, Sonication.</em>

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9

Khandekar, Amit C., and Bhushan M. Khadilkar. "Pechmann Reaction in Chloroaluminate Ionic Liquid." Synlett 2002, no. 01 (2002): 0152–54. http://dx.doi.org/10.1055/s-2002-19332.

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10

Stoyanov, E., and J. Mezger. "Pechmann Reaction Promoted by Boron Trifluoride Dihydrate." Molecules 10, no. 7 (2005): 762–66. http://dx.doi.org/10.3390/10070762.

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11

Chattha, Fauzia Anjum, Saeed Ahmed Nagra, and Munawar Ali Munawar. "A REVISIT OF PECHMANN REACTION UNDER MICROWAVE RADIATION." Indonesian Journal of Chemistry 8, no. 1 (2010): 94–96. http://dx.doi.org/10.22146/ijc.21659.

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A series of coumarins have been prepared by the Pechmann reaction of different phenols with ethyl acetoactate as well as malic acid using catalytic amount of sulfuric acid under microwave irradiation for few seconds. Keywords: Pechman reaction, Coumarins, Microwave irradiation

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12

Daru, János, and András Stirling. "Mechanism of the Pechmann Reaction: A Theoretical Study." Journal of Organic Chemistry 76, no. 21 (2011): 8749–55. http://dx.doi.org/10.1021/jo201439u.

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13

Khandekar, Amit C., and Bhushan M. Khadilkar. "ChemInform Abstract: Pechmann Reaction in Chloroaluminate Ionic Liquid." ChemInform 33, no. 20 (2010): no. http://dx.doi.org/10.1002/chin.200220103.

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14

Khodabakhshi, Saeed. "Barium Dichloride as a Powerful and Inexpensive Catalyst for the Pechmann Condensation without Using Solvent." Organic Chemistry International 2012 (November 4, 2012): 1–5. http://dx.doi.org/10.1155/2012/306162.

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Various coumarin derivatives have been efficiently synthesized via barium dichloride-catalyzed Pechmann condensation reaction of various phenols and β-keto esters under solvent-free conditions. This novel and inexpensive method has advantages such as short reaction times, excellent product yields, and avoidance of organic solvents in agreement with green chemistry principles.

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15

Torviso, R., D. Mansilla, A. Belizán, et al. "Catalytic activity of Keggin heteropolycompounds in the Pechmann reaction." Applied Catalysis A: General 339, no. 1 (2008): 53–60. http://dx.doi.org/10.1016/j.apcata.2008.01.020.

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16

Yan, Weitao, Ruo Wang, Tesen Zhang, et al. "Synthesis of 4-trifluoromethyl 2-pyrones and pyridones through the Brønsted base-catalyzed Pechmann-type reaction with cyclic 1,3-diones." Organic & Biomolecular Chemistry 16, no. 48 (2018): 9440–45. http://dx.doi.org/10.1039/c8ob02701c.

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17

Brady, William T., and Yi-Qi Gu. "Benzofurans. Ketene intermediates in the perkin reaction." Journal of Heterocyclic Chemistry 25, no. 3 (1988): 969–71. http://dx.doi.org/10.1002/jhet.5570250350.

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18

Dinesh, N. Navale, B. Ranade Prasanna, W. Zote Santosh, J. Wagh Swapnil, and K. Kulal Dnyaneshwar. "Eco-Friendly One Pot Synthesis of Coumarin Derivatives by Pechmann Condensation using Tamarind Juice as a Biocatalyst." International Journal of Innovative Science and Research Technology 8, no. 2 (2023): 1917–20. https://doi.org/10.5281/zenodo.7716411.

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An efficient and eco-friendly synthetic method has been established for synthesis of 7-hydroxy-4-methyl coumarin and its derivatives using tamarind juice as a biocatalyst. The condensation reaction of Substituted phenol with ethyl acetoacetate (EAA) successfully carried out using tamarind juice as a green and efficient catalyst at 90°C in aqueous condition. This green biocatalyst has been utilised effectively for pechmann reaction with good yield of product, easy workup and eco-friendly reaction conditions.

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19

Amoozadeh, Ali, Majid Ahmadzadeh, and Eskandar Kolvari. "Easy Access to Coumarin Derivatives Using Alumina Sulfuric Acid as an Efficient and Reusable Catalyst under Solvent-Free Conditions." Journal of Chemistry 2013 (2013): 1–6. http://dx.doi.org/10.1155/2013/767825.

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A new and efficient condition for the use of alumina sulfuric acid (ASA) as a heterogeneous catalyst in the Pechmann condensation reaction in solvent-free condition for the formation of coumarins has been reported.

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20

Manhas, Maghar S., Subhendu N. Ganguly, Somdatta Mukherjee, Amit K. Jain, and Ajay K. Bose. "Microwave initiated reactions: Pechmann coumarin synthesis, Biginelli reaction, and acylation." Tetrahedron Letters 47, no. 14 (2006): 2423–25. http://dx.doi.org/10.1016/j.tetlet.2006.01.147.

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21

Kalita, Pranjal, and Rajiv Kumar. "Solvent-free coumarin synthesis via Pechmann reaction using solid catalysts." Microporous and Mesoporous Materials 149, no. 1 (2012): 1–9. http://dx.doi.org/10.1016/j.micromeso.2011.08.004.

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22

Heravi, Majid M., Soheila Khaghaninejad, and Manizhe Mostofi. "ChemInform Abstract: Pechmann Reaction in the Synthesis of Coumarin Derivatives." ChemInform 46, no. 22 (2015): no. http://dx.doi.org/10.1002/chin.201522281.

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23

Joshi, J., M. K. Mishra, and M. Srinivasarao. "Silica-supported methanesulfonic acid — An efficient solid Brønsted acid catalyst for the Pechmann reaction in the presence of higher n-alkanes." Canadian Journal of Chemistry 89, no. 6 (2011): 663–70. http://dx.doi.org/10.1139/v11-055.

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A cost-effective and efficient solid Brønsted acid catalyst was synthesized by loading methanesulfonic acid (MSA) on silica and was used for the acid-catalyzed Pechmann reaction to test the catalytic activity and its reusability. Derivatives of 4-methylcoumarin were synthesized in good yields within short reaction times in the presence of environmentally friendly higher n-alkanes as solvents. The regeneration study of the spent catalyst showed satisfactory results.

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24

Osborne, Alan G., Steven J. Andrews, and Rachel Mower. "Further studies of Orientation Effects in the Pechmann synthesis of Coumarins." Journal of Chemical Research 2003, no. 3 (2003): 114–15. http://dx.doi.org/10.3184/030823403103173327.

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The proportion of 5-/7- substituted coumarins formed in the Pechmann synthesis from meta-substituted phenols and malic acid and ethyl acetoacetate under a variety of reaction conditions, with product analysis by 1H and 13C NMR spectroscopy, is reported.

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25

MOHAMED, ABBAS METWALLY, and M. KHALIL ABDEL-GALIL. "Synthesis of Azabicyclo[3.3.1 ]nonanes and Dibenzo[b,d]pyrans from 3-Aryl-2,4-dicarboethoxy-5-hydroxy-5-methyl-cyclohexanones as Potential Antimicrobial Agents." Journal of Indian Chemical Society Vol. 65, Nov 1988 (1988): 766–67. https://doi.org/10.5281/zenodo.6087498.

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Department of Chemistry, Faculty of Science, University of Mansoura, Mansoura, Egypt <em>Manuscript received 19 January 1988, revised 27  May 1988, accepted 2 August 1988</em> Double Mannich reaction or 1a, c with formalin and benzylamine or cyclohexylamine gave 3-azabicyclo [3 3.1] nonane derivatives (2a, b), while  the Pechmann reaction of 1a, c gave the dlbenzopyrans (4, 5). The structures of the compounds have been confirmed by ir, pmr and mass spectral data.

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26

Smitha, G., and Ch Sanjeeva Reddy. "ZrCl4‐Catalyzed Pechmann Reaction: Synthesis of Coumarins Under Solvent‐Free Conditions." Synthetic Communications 34, no. 21 (2004): 3997–4003. http://dx.doi.org/10.1081/scc-200034821.

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27

Tyndall, Stephen, Koon Fai Wong, and Melissa A. VanAlstine-Parris. "Insight into the Mechanism of the Pechmann Condensation Reaction Using NMR." Journal of Organic Chemistry 80, no. 18 (2015): 8951–53. http://dx.doi.org/10.1021/acs.joc.5b01802.

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28

Sunil Kumar, B., P. S. Kumar, N. Srinivasulu, et al. "Vanadium(III) chloride as an effective catalyst for the Pechmann reaction." Chemistry of Heterocyclic Compounds 42, no. 2 (2006): 172–75. http://dx.doi.org/10.1007/s10593-006-0066-6.

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29

Lakouraj, Moslem Mansour, Nazanin Bagheri, and Vahid Hasantabar. "Synthesis and Application of Nanocrystalline-Cellulose-Supported Acid Ionic Liquid Catalyst in Pechmann Reaction." International Journal of Carbohydrate Chemistry 2013 (October 29, 2013): 1–8. http://dx.doi.org/10.1155/2013/452580.

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Nanocrystalline-cellulose-supported acidic ionic liquid carrying SO3H functional group was prepared using nanocrystalline cellulose, imidazole and 1,4-butane sultone as the source chemicals. The prepared nanocrystalline-cellulose-supported ionic liquid catalyst was characterized by AFM and SEM and its catalytic activity in the reaction of resorcinol with ethyl acetoacetate was tested in a solvent-free condition. The effects of reaction time, reaction temperature, and the ratio of catalyst on the conversion of resorcinol were investigated. A variety of coumarin derivatives were obtained in good

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30

Ojima, Fumihiro, and Tetsuo Osa. "Perkin–Markovnikov Type Reaction Initiated with Electrogenerated Superoxide Ion." Bulletin of the Chemical Society of Japan 62, no. 10 (1989): 3187–94. http://dx.doi.org/10.1246/bcsj.62.3187.

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31

Edwards, Mark, Paul M. Rourk, Philip G. Riby, and Andrew P. Mendham. "Not quite the last word on the Perkin reaction." Tetrahedron 70, no. 40 (2014): 7245–52. http://dx.doi.org/10.1016/j.tet.2014.07.053.

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32

Ojima, Fumihiro, Tomokazu Matsue, and Tetsuo Osa. "Perkin–Markovnikov Type Reaction Initiated with Electrogenerated Superoxide Ion." Chemistry Letters 16, no. 11 (1987): 2235–38. http://dx.doi.org/10.1246/cl.1987.2235.

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33

Petrosyan, V. A., A. A. Vasil'ev, and V. I. Tatarinova. "Electrosynthesis of cyclopropane derivatives by a Perkin-type reaction." Russian Chemical Bulletin 43, no. 1 (1994): 84–88. http://dx.doi.org/10.1007/bf00699141.

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34

Zhang, Yuehua, Anlian Zhu, Qianqian Li, Lingjun Li, Yang Zhao, and Jianji Wang. "Cholinium ionic liquids as cheap and reusable catalysts for the synthesis of coumarins via Pechmann reaction under solvent-free conditions." RSC Adv. 4, no. 44 (2014): 22946–50. http://dx.doi.org/10.1039/c4ra02227k.

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Ionic liquid [N<sub>112</sub>OH][HSO<sub>4</sub>] was found to be an efficient and reusable catalyst for Pechmann reaction under solvent-free conditions. UV-vis studies suggested that the high catalytic performance of this catalyst was mainly due to its ability to increase the content of keto tautomer of ethyl acetoacetate.

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35

Aoudjit, L., D. Halliche, K. Bachari, A. Saadi, and O. Cherifi. "Nickel-Containing Mesoporous Silicas as a Catalyst for the Pechmann Condensation Reaction." Theoretical and Experimental Chemistry 53, no. 2 (2017): 112–21. http://dx.doi.org/10.1007/s11237-017-9507-9.

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36

Gu, Yanlong, Juan Zhang, Zhiying Duan, and Youquan Deng. "Pechmann Reaction in Non-Chloroaluminate Acidic Ionic Liquids under Solvent-Free Conditions." Advanced Synthesis & Catalysis 347, no. 4 (2005): 512–16. http://dx.doi.org/10.1002/adsc.200404316.

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37

Kalita, Pranjal, and Rajiv Kumar. "ChemInform Abstract: Solvent-Free Coumarin Synthesis via Pechmann Reaction Using Solid Catalysts." ChemInform 43, no. 3 (2011): no. http://dx.doi.org/10.1002/chin.201203222.

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38

Calamante, Massimo, Gianna Reginato, Alessio Dessì, Matteo Bartolini, Lorenzo Zani, and Alessandro Mordini. "Extending the Conjugation of Pechmann Lactone Thienyl Derivatives: A New Class of Small Molecules for Organic Electronics Application." Synthesis 50, no. 06 (2017): 1284–92. http://dx.doi.org/10.1055/s-0036-1591856.

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The preparation and spectroscopic characterization of some symmetrical small molecules containing the disubstituted (E)-3,3′-bifuranylidene-2,2′-dione chromophore (the so-called Pechmann lactone) and featuring an extended conjugation are reported. The synthetic approach of such compounds is based on the Stille–Migita coupling reaction, which is carried out in very mild conditions, suitable to be applied with the very sensitive Pechmann core. The absorption and emission spectra of the new molecules obtained have been recorded in solution and clearly show how their photophysical properties can b

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39

Veverkova, E., E. Pacherova, and S. Toma. "ChemInform Abstract: Examination of the Perkin Reaction under Microwave Irradiation." ChemInform 31, no. 10 (2010): no. http://dx.doi.org/10.1002/chin.200010100.

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40

Polya, J. B., and T. M. Spotswood. "Amides VII. The use of diacylimines in the perkin reaction." Recueil des Travaux Chimiques des Pays-Bas 70, no. 2 (2010): 146–54. http://dx.doi.org/10.1002/recl.19510700208.

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41

Hosny, Mona A., Hyam A. Radwan, and Emtithal A. El-Sawi. "Synthesis and Anticancer Activity of Some New Derivatives of Coumarin and Quinolinyl Mercaptotriazoles." E-Journal of Chemistry 9, no. 4 (2012): 1737–45. http://dx.doi.org/10.1155/2012/365647.

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Pechmann condensation of ethylacetoacetate with derivatives of phenol by heating in absence of solvent and with montmorillonite clays K-10 afforded coumarin derivatives(1a-e)in good yields which on reaction with thiosemicarbazide in anhydrous pyridine yielded coumarin-quinolinyl mercaptotriazole(2a-e). The latter compounds were evaluated for their antimicrobial and anticancer activities. The newly synthesized compounds were characterized by IR,1HNMR and mass spectra.

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42

Badea, Irinel, Philippe Cotelle, and Jean-Pierre Catteau. "AN EFFICIENT METHOD FOR THE SYNTHESIS OF NEW SUBSTITUTED CHROMENS." SOUTHERN BRAZILIAN JOURNAL OF CHEMISTRY 9, no. 10 (2001): 1–4. http://dx.doi.org/10.48141/sbjchem.v9.n10.2001.4_2001.pdf.

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43

Sharapov, Ainur D., Ramil F. Fatykhov, Igor A. Khalymbadzha, et al. "Fluorescent Pyranoindole Congeners: Synthesis and Photophysical Properties of Pyrano[3,2-f], [2,3-g], [2,3-f], and [2,3-e]Indoles." Molecules 27, no. 24 (2022): 8867. http://dx.doi.org/10.3390/molecules27248867.

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This paper reports the synthesis of four types of annulated pyranoindole congeners: pyrano[3,2-f]indole, pyrano[2,3-g]indole, pyrano[2,3-f]indole, and pyrano[2,3-e]indole and photophysical studies in this series. The synthesis of pyrano[3,2-f], [2,3-g], and [2,3-e]indoles involve a tandem of Bischler–Möhlau reaction of 3-aminophenol with benzoin to form 6-hydroxy- or 4-hydroxyindole followed by Pechmann condensation of these hydroxyindoles with β-ketoesters. Pyrano[2,3-f]indoles were synthesized through the Nenitzescu reaction of p-benzoquinone and ethyl aminocrotonates and subsequent Pechmann

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44

EL-Dafrawy, Shady M., Shawky M. Hassan, and Mervat Farag. "Kinetics and mechanism of Pechmann condensation reaction over sulphated zirconia-supported zinc oxide." Journal of Materials Research and Technology 9, no. 1 (2020): 13–21. http://dx.doi.org/10.1016/j.jmrt.2019.09.063.

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45

Luck, Rudy L., and G. David Mendenhall. "(2-Ethoxycarbonyl-3,5-dihydroxyphenyl)acetic acid monohydrate, an intermediate in the Pechmann reaction." Acta Crystallographica Section E Structure Reports Online 58, no. 12 (2002): o1387—o1388. http://dx.doi.org/10.1107/s1600536802020627.

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46

Wu, Jie, Tianning Diao, Wei Sun, and Yizhe Li. "Expeditious Approach to Coumarins via Pechmann Reaction Catalyzed by Molecular Iodine or AgOTf." Synthetic Communications 36, no. 20 (2006): 2949–56. http://dx.doi.org/10.1080/00397910600773692.

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47

Opanasenko, Maksym, Mariya Shamzhy, and Jiří Čejka. "Solid Acid Catalysts for Coumarin Synthesis by the Pechmann Reaction: MOFs versus Zeolites." ChemCatChem 5, no. 4 (2012): 1024–31. http://dx.doi.org/10.1002/cctc.201200232.

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48

Mzozoyana, Vuyisa, Fanie R. van Heerden, and Craig Grimmer. "Synthesis of 4-(2-fluorophenyl)-7-methoxycoumarin: experimental and computational evidence for intramolecular and intermolecular C–F···H–C bonds." Beilstein Journal of Organic Chemistry 16 (February 10, 2020): 190–99. http://dx.doi.org/10.3762/bjoc.16.22.

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4-(2-Fluorophenyl)-7-methoxycoumarin (6) was synthesized by Pechmann reaction under mild conditions via a three-step reaction. The solution-state 1H NMR spectra of 6 showed a strong intramolecular interaction between F and H5 (J FH = 2.6 Hz) and 13C NMR suggested that this C–F···H–C coupling is a through-space interaction. The 2D 19F-{1H} HOESY and 1H-{19F} 1D experiments were done to confirm this F···H interaction. The single crystal X-ray structure and the DFT-optimized structure showed that the fluorinated phenyl ring favors the orientation with the fluorine atom closer to H5 than H3. The X

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49

Becerra-Anaya, Silvia J., Diego R. Merchán Arenas, and Vladimir V. Kouznetsov. "A Simple and Effective Protocol for the Pechmann Reaction to Obtain 4-Methylcoumarin Derivatives Using a High-Speed Mixer Ball Mill Process." Chemistry 5, no. 2 (2023): 1077–88. http://dx.doi.org/10.3390/chemistry5020073.

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We hereby report a simple and efficient method for the preparation of 4-methylcoumarins series, including Coumarin 120 (7-amino-4-methylcoumarin) from phenols (or naphthols) and ethyl acetoacetate in the presence of 3 mol% InCl3. Coumarins were obtained in good yields (52–92%) through Pechmann condensation, under a rapid and environmentally friendly protocol using a high-speed ball mill mixer at room temperature, with short reaction times, under solvent-free conditions.

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50

Sevenard, Dmitri V. "3-Polyfluoroalkyl-substituted E-cinnamic acids: easy access via Perkin reaction." Tetrahedron Letters 44, no. 38 (2003): 7119–20. http://dx.doi.org/10.1016/s0040-4039(03)01830-6.

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