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Journal articles on the topic 'Gewald reaction'

Author: Grafiati
Published: 24 April 2022
Last updated: 29 May 2022

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1

Huang, Yijun, and Alexander Dömling. "The Gewald multicomponent reaction." Molecular Diversity 15, no. 1 (February 27, 2010): 3–33. http://dx.doi.org/10.1007/s11030-010-9229-6.

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2

Gouda, Moustafa. "LiOH.H2O as a catalyst for Knoevenagel and Gewald reactions." Polish Journal of Chemical Technology 12, no. 4 (January 1, 2010): 31–35. http://dx.doi.org/10.2478/v10026-010-0046-6.

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LiOH.H2O as a catalyst for Knoevenagel and Gewald reactions Commercial available lithium hydroxide monohydrate LiOH.H2O was found to be a novel ‘dual activation’ catalyst for tandem cross Knoevenagel condensation between malononitrile or ethylcyanoacetate and aromatic aldehydes leading to an efficient and easy synthesis of the corresponding arylidenes at room temperature in a short reaction time. In the case of salicyaldehyde the reaction lead to the formation of 3-substituted coumarins. The high efficacy, cheapness and easy availability of LiOH.H2O prompted us to investigate its validity as a basic catalyst for Gewald reaction.
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3

Sabnis, Ram W. "The Gewald reaction in dye chemistry." Coloration Technology 132, no. 1 (January 28, 2016): 49–82. http://dx.doi.org/10.1111/cote.12182.

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4

Sabnis, R. W., D. W. Rangnekar, and N. D. Sonawane. "2-aminothiophenes by the gewald reaction." Journal of Heterocyclic Chemistry 36, no. 2 (March 1999): 333–45. http://dx.doi.org/10.1002/jhet.5570360203.

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5

Huang, Yijun, and Alexander Doemling. "ChemInform Abstract: The Gewald Multicomponent Reaction." ChemInform 42, no. 34 (July 28, 2011): no. http://dx.doi.org/10.1002/chin.201134257.

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6

Mallia, Carl J., Lukas Englert, Gary C. Walter, and Ian R. Baxendale. "Thiazole formation through a modified Gewald reaction." Beilstein Journal of Organic Chemistry 11 (May 26, 2015): 875–83. http://dx.doi.org/10.3762/bjoc.11.98.

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The synthesis of thiazoles and thiophenes starting from nitriles, via a modified Gewald reaction has been studied for a number of different substrates. 1,4-Dithiane-2,5-diol was used as the aldehyde precursor to give either 2-substituted thiazoles or 2-substituted aminothiophenes depending on the substitution of the α-carbon to the cyano group.
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7

Thomas, Joice, Sampad Jana, Mahendra Sonawane, Bert Fiey, Jan Balzarini, Sandra Liekens, and Wim Dehaen. "A new four-component reaction involving the Michael addition and the Gewald reaction, leading to diverse biologically active 2-aminothiophenes." Organic & Biomolecular Chemistry 15, no. 18 (2017): 3892–900. http://dx.doi.org/10.1039/c7ob00707h.

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A Gewald-four component reaction has been successfully developed for the synthesis of a series of compounds containing an indole and a 2-aminothiophene moiety separated by a methylene spacer having anti-proliferative activity.
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8

Sridhar, Madabhushi, Rayankula Mallikarjuna Rao, Nanduri H. K. Baba, and Ravindra M. Kumbhare. "Microwave accelerated Gewald reaction: synthesis of 2-aminothiophenes." Tetrahedron Letters 48, no. 18 (April 2007): 3171–72. http://dx.doi.org/10.1016/j.tetlet.2007.03.052.

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9

Sabnis, R. W., D. W. Rangnekar, and N. D. Sonawane. "ChemInform Abstract: 2-Aminothiophenes by the Gewald Reaction." ChemInform 30, no. 36 (June 13, 2010): no. http://dx.doi.org/10.1002/chin.199936290.

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10

Mallia, Carl J., Lukas Englert, Gary C. Walter, and Ian R. Baxendale. "ChemInform Abstract: Thiazole Formation Through a Modified Gewald Reaction." ChemInform 46, no. 33 (July 28, 2015): no. http://dx.doi.org/10.1002/chin.201533173.

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11

Lu, Lian Ying, Zhong Shan Yu, Zheng Dong Fang, Yong Zhou Chen, Wen Zhou, Xian Hong Wei, and Qing Tao. "Synthesis and Characterization of New 2-Methoxy-Thieno[2,3-d]pyrimidin-4(3H)-One." Advanced Materials Research 550-553 (July 2012): 89–92. http://dx.doi.org/10.4028/www.scientific.net/amr.550-553.89.

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An efficient method is described for the synthesis of 2-methoxy-thieno[2,3-d]pyrimidin- 4(3H)-one (5) via Gewald reaction, a tandem aza-Wittig reaction and cyclization process. The key step is an aza-Wittig reaction between iminophosphorane (2), 4-chlorophenyl isocyanine and nucleophilic reagent CH3OH. Its structures were determined by means of MS, IR and 1H NMR spectra.
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12

Abaee, M. Saeed, and Somayeh Cheraghi. "A facile four-component Gewald reaction under organocatalyzed aqueous conditions." Arkivoc 2014, no. 4 (December 16, 2013): 1–10. http://dx.doi.org/10.3998/ark.5550190.p008.427.

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13

Puterova, Zita, Alžbeta Krutošíková, and Daniel Végh. "Gewald reaction: synthesis, properties and applications of substituted 2-aminothiophenes." Arkivoc 2010, no. 1 (July 9, 2010): 209–46. http://dx.doi.org/10.3998/ark.5550190.0011.105.

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14

Adib, Mehdi, Mehd Soheilizad, Saideh Rajai-daryasaraei, and Peiman Mirzaei. "An Efficient Aromatization of 2-Amino-4,5,6,7-tetrahydrobenzo-[b]thiophene-3-carboxylates in Dimethyl Sulfoxide Catalyzed by p-Toluenesulfonic Acid." Synlett 26, no. 08 (March 5, 2015): 1101–5. http://dx.doi.org/10.1055/s-0034-1379998.

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A novel oxidation–aromatization of alkyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylates is reported. The Gewald product, obtained from three-component condensation reaction between a cyclohexanone, an alkyl cyanoacetate, and sulfur, underwent an oxidation reaction in dimethyl sulfoxide in the presence of a catalytic amount of p-toluenesulfonic acid to give the corresponding alkyl 2-aminobenzo[b]thiophene-3-carboxylate in excellent yield.
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15

Eller, Gernot, and Wolfgang Holzer. "First Synthesis of 3-Acetyl-2-aminothiophenes Using the Gewald Reaction." Molecules 11, no. 5 (May 16, 2006): 371–76. http://dx.doi.org/10.3390/11050371.

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16

Castanedo, Georgette M., and Daniel P. Sutherlin. "Synthesis of tetrasubstituted thiophenes on solid-support using the Gewald reaction." Tetrahedron Letters 42, no. 41 (October 2001): 7181–84. http://dx.doi.org/10.1016/s0040-4039(01)01470-8.

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17

Yang, Guichun, Haiqing Zhang, Jianian Chen, and Zuxing Chen. "Synthesis of Thiophene Derivatives on Soluble Polymer-Support Using Gewald Reaction." Synthesis, no. 18 (2004): 3055–59. http://dx.doi.org/10.1055/s-2004-834895.

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18

GUETSCHOW, M., H. SCHROETER, G. KUHNLE, and K. EGER. "ChemInform Abstract: Synthesis of 4-Isobutyl Substituted Thiophenes by Gewald Reaction." ChemInform 27, no. 27 (August 5, 2010): no. http://dx.doi.org/10.1002/chin.199627139.

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19

Wang, Dai Fu, Hui Gao, Xiao Hong Tan, Wen Meng Li, Jing Wang, Ya Jie Wu, and Xin Jian Song. "Facile Synthesis and Crystal Structure of N-(3-Cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-2,2,2-trifluoroacetamide." Advanced Materials Research 887-888 (February 2014): 661–64. http://dx.doi.org/10.4028/www.scientific.net/amr.887-888.661.

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N-(3-Cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-2,2,2-trifluoroacetamide was synthesized by the acylation reaction of trifluoroacetic anhydride with 2-amino-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carbonitrile, which was prepared via microwave-assisted Gewald reaction with K2CO3 as a heterogeneous solid base catalyst. This protocol presented such advantages as short reaction time, high yield, easy work-up and environmentally benign procedures. The structure of the title compound was confirmed by IR, 1H NMR, MS, elemental analysis and X-ray single-crystal diffraction method. X-Ray diffraction analysis reveals that the cyclohexene ring adopts a half-chair conformation and the thiophene ring is essentially planar.
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20

Al-Mousawi, Saleh, Moustafa Sherief Moustafa, and Mohamed Hilmy Elnagdi. "Studies with enamines: Functionally substituted enamines as aldehyde equivalents in Gewald reaction." Arkivoc 2008, no. 10 (November 28, 2007): 17–25. http://dx.doi.org/10.3998/ark.5550190.0009.a03.

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21

Mekheimer, Ramadan Ahmed, Mohamed Abdallah Ameen, and Kamal Usef Sadek. "Solar thermochemical reactions II1: Synthesis of 2-aminothiophenes via Gewald reaction induced by solar thermal energy." Chinese Chemical Letters 19, no. 7 (July 2008): 788–90. http://dx.doi.org/10.1016/j.cclet.2008.04.041.

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22

Li, Pengyu, Yuanyuan Liu, Lu Wang, Minli Tao, and Wenqin Zhang. "Modified polyacrylonitrile fiber as a renewable heterogeneous base catalyst for Henry reaction and Gewald reaction in water." Journal of Applied Polymer Science 135, no. 11 (November 16, 2017): 45992. http://dx.doi.org/10.1002/app.45992.

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23

Abaee, M. Saeed, Atefeh Hadizadeh, Mohammad M. Mojtahedi, and Mohammad R. Halvagar. "Exploring the scope of the Gewald reaction: Expansion to a four-component process." Tetrahedron Letters 58, no. 14 (April 2017): 1408–12. http://dx.doi.org/10.1016/j.tetlet.2017.02.071.

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24

Puterová, Zita, Anita Andicsová, and Daniel Végh. "Synthesis of π-conjugated thiophenes starting from substituted 3-oxopropanenitriles via Gewald reaction." Tetrahedron 64, no. 49 (December 2008): 11262–69. http://dx.doi.org/10.1016/j.tet.2008.09.032.

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25

Rezaei-Seresht, Esmail, Reza Tayebee, and Mohammad Yasemi. "KG-60-Piperazine as a New Heterogeneous Catalyst for Gewald Three-Component Reaction." Synthetic Communications 43, no. 13 (January 2, 2013): 1859–64. http://dx.doi.org/10.1080/00397911.2012.674607.

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26

Zhao, Dan-Dan, Li Li, Fan Xu, Qi Wu, and Xian-Fu Lin. "Bovine serum albumin-catalyzed one-pot synthesis of 2-aminothiophenes via Gewald reaction." Journal of Molecular Catalysis B: Enzymatic 95 (November 2013): 29–35. http://dx.doi.org/10.1016/j.molcatb.2013.05.014.

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27

Hu, Yi, Ping Wei, He Huang, Shi‐Qing Han, and Ping‐Kai Ouyang. "Synthesis of 2‐Aminothiophenes on Ionic Liquid Phase Support using the Gewald Reaction." Synthetic Communications 36, no. 11 (June 1, 2006): 1543–48. http://dx.doi.org/10.1080/00397910600588819.

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28

Buchstaller, Hans-Peter, Carsten D. Siebert, Ralf H. Lyssy, Ina Frank, Adil Duran, Rudolf Gottschlich, and Christian R. Noe. "Synthesis of Novel 2-Aminothiophene-3-carboxylates by Variations of the Gewald Reaction." Monatshefte fuer Chemie/Chemical Monthly 132, no. 2 (February 15, 2001): 279–93. http://dx.doi.org/10.1007/s007060170137.

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29

ABAEE, Mohammad Saeed, and Somayeh CHERAGHI. "Aqueous DABCO, an efficient medium for rapid organocatalyzed Knoevenagel condensation and the Gewald reaction." TURKISH JOURNAL OF CHEMISTRY 38 (2014): 650–60. http://dx.doi.org/10.3906/kim-1309-38.

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30

Dodiya, Dipti, Amit Trivedi, Samir Jarsania, Shailesh Vaghasia, and Viresh Shah. "Characterization and biological evaluation of some novel pyrazolo[3',4':4,5]thieno[2,3-d]pyrimidin-8-ones synthesized via the Gewald reaction." Journal of the Serbian Chemical Society 73, no. 7 (2008): 683–90. http://dx.doi.org/10.2298/jsc0807683d.

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The synthesis of substituted pyrazolo[3',4':4,5]thieno[2,3-d]pyrimidin-8-ones (IIIa-j) from 5-amino-3-methyl-1H-thieno[3,2-c]pyrazole-6-carbonitrile (II) is described. The key compound II was synthesized from (5-methyl- -2,4-dihydro-3H-pyrazol-3-ylidene)malononitrile I via the Gewald reaction. The synthesis of the title compounds IIIa-j was accomplished by condensation of II with different aromatic aldehydes. The newly synthesized heterocyles were characterized by elemental analysis, IR, 1H-NMR, 13C-NMR and mass spectroscopic investigation. All the newly synthesized compounds were evaluated for antimicrobial activity against a variety of bacterial strains. .
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31

Yamuna, Ezhumalai, Matthias Zeller, Philip O. Adero, and Karnam Jayaramapillai Rajendra Prasad. "Synthesis of thieno- and benzocyclohepta[b]indoles: Gewald reaction and regioselective cycloaddition of acetylenic esters." Arkivoc 2012, no. 6 (May 21, 2012): 326–42. http://dx.doi.org/10.3998/ark.5550190.0013.630.

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32

Moeinpour, Farid, Raheleh Omidinia, Nadieh Dorostkar-Ahmadi, and Bentalhoda Khoshdeli. "Cesium Carbonate as a Heterogeneous Base Catalyst for Synthesis of 2-Aminothiophenes via Gewald Reaction." Bulletin of the Korean Chemical Society 32, no. 6 (June 20, 2011): 2091–92. http://dx.doi.org/10.5012/bkcs.2011.32.6.2091.

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33

Shearouse, William, Maxwell Shumba, and James Mack. "A Solvent-Free, One-Step, One-Pot Gewald Reaction for Alkyl-aryl Ketones via Mechanochemistry." Applied Sciences 4, no. 2 (April 8, 2014): 171–79. http://dx.doi.org/10.3390/app4020171.

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34

Mojtahedi, Mohammad M., M. Saeed Abaee, Peyman Mahmoodi, and Mehdi Adib. "Convenient Synthesis of 2-Aminothiophene Derivatives by Acceleration of Gewald Reaction Under Ultrasonic Aqueous Conditions." Synthetic Communications 40, no. 14 (June 17, 2010): 2067–74. http://dx.doi.org/10.1080/00397910903219435.

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35

Bagherpour, Saeed, Mohammad M. Mojtahedi, and M. Saeed Abaee. "Applying Gewald reaction for the preparation of some novel aminothieno derivatives featuring noroxymorphone skeletal backbone." Journal of Sulfur Chemistry 41, no. 3 (February 19, 2020): 301–9. http://dx.doi.org/10.1080/17415993.2020.1729761.

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36

Rezaei-Seresht, Esmail, Reza Tayebee, and Mohammad Yasemi. "ChemInform Abstract: KG-60-Piperazine as a New Heterogeneous Catalyst for Gewald Three-Component Reaction." ChemInform 44, no. 40 (September 12, 2013): no. http://dx.doi.org/10.1002/chin.201340102.

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37

Wang, Dao-Lin, Jian-Ying Wu, and Qing-Tao Cui. "An efficient one-pot synthesis of thiophene-fused pyrido[3,2-a]azulenes via Gewald reaction." Chinese Chemical Letters 25, no. 12 (December 2014): 1591–94. http://dx.doi.org/10.1016/j.cclet.2014.07.007.

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38

Buchstaller, Hans-Peter, Carsten D. Siebert, Ralf H. Lyssy, Ina Frank, Adil Duran, Rudolf Gottschlich, and Christian R. Noe. "ChemInform Abstract: Synthesis of Novel 2-Aminothiophene-3-carboxylates by Variations of the Gewald Reaction." ChemInform 32, no. 21 (May 26, 2010): no. http://dx.doi.org/10.1002/chin.200121097.

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39

Shyyka, O., M. Svyrydenko, M. Tupychak, N. Pokhodylo, and M. Obushak. "Synthesis of novel 3-(1,2,4-oxadiazol-5-yl)thiophen-2-amine derivatives via gewald reaction." Visnyk of the Lviv University. Series Chemistry 62, no. 1 (2021): 183. http://dx.doi.org/10.30970/vch.6201.183.

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40

Islam, Farhana, Arpit Doshi, Andrew J. Robles, Tasdique M. Quadery, Xin Zhang, Xilin Zhou, Ernest Hamel, Susan L. Mooberry, and Aleem Gangjee. "Design, Synthesis, and Biological Evaluation of 5,6,7,8-Tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidines as Microtubule Targeting Agents." Molecules 27, no. 1 (January 5, 2022): 321. http://dx.doi.org/10.3390/molecules27010321.

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A series of eleven 4-substituted 5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidines were designed and synthesized and their biological activities were evaluated. Synthesis involved the Gewald reaction to synthesize ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate ring, and SNAr reactions. Compound 4 was 1.6- and ~7-fold more potent than the lead compound 1 in cell proliferation and microtubule depolymerization assays, respectively. Compounds 4, 5 and 7 showed the most potent antiproliferative effects (IC50 values < 40 nM), while compounds 6, 8, 10, 12 and 13 had lower antiproliferative potencies (IC50 values of 53–125 nM). Additionally, compounds 4–8, 10 and 12–13 circumvented Pgp and βIII-tubulin mediated drug resistance, mechanisms that diminish the clinical efficacy of paclitaxel (PTX). In the NCI-60 cell line panel, compound 4 exhibited an average GI50 of ~10 nM in the 40 most sensitive cell lines. Compound 4 demonstrated statistically significant antitumor effects in a murine MDA-MB-435 xenograft model.
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41

Huang, Xian-Gui, Jia Liu, Jiangmeng Ren, Tao Wang, Weidong Chen, and Bu-Bing Zeng. "A facile and practical one-pot synthesis of multisubstituted 2-aminothiophenes via imidazole-catalyzed Gewald reaction." Tetrahedron 67, no. 34 (August 2011): 6202–5. http://dx.doi.org/10.1016/j.tet.2011.06.061.

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42

Said, Noureddine, Soufiane Touil, Azaiez Ben Akacha, and Mohamed Lotfi Efrit. "Reactivite Des α -Phosphonylketones Dans la Reaction de Gewald: Synthese de Nouveaux Derives de L′aminophosphonothiophene." Phosphorus, Sulfur, and Silicon and the Related Elements 183, no. 11 (October 7, 2008): 2726–33. http://dx.doi.org/10.1080/10426500801969357.

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43

Chavan, Sunil S., Yogesh Y. Pedgaonkar, Ananda J. Jadhav, and Mariam S. Degani. "ChemInform Abstract: Microwave Accelerated Synthesis of 2-Aminothiophenes in Ionic Liquid via Three Component Gewald Reaction." ChemInform 43, no. 32 (July 12, 2012): no. http://dx.doi.org/10.1002/chin.201232106.

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44

Nirogi, Ramakrishna V. S., Rama Sastri Kambhampati, Prabhakar Kothmirkar, Sobhanadri Arepalli, Narasimha Reddy G. Pamuleti, Anil K. Shide, and P. K. Dubey. "ChemInform Abstract: Convenient and Efficient Synthesis of Some Novel Fused Thieno Pyrimidines Using Gewald′s Reaction." ChemInform 43, no. 11 (February 16, 2012): no. http://dx.doi.org/10.1002/chin.201211147.

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45

Hallas, Geoffrey, and Andrew D. Towns. "Dyes derived from aminothiophenes. Part 1: Synthesis of some heterocyclic disperse dyes using the gewald reaction." Dyes and Pigments 32, no. 3 (November 1996): 135–49. http://dx.doi.org/10.1016/0143-7208(96)00024-1.

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46

Nguyen, Thanh Binh, Dinh Hung Mac, and Pascal Retailleau. "Base-Catalyzed Three-Component Reaction of α-Cyanoacetates with Chalcones and Elemental Sulfur: Access to 2-Aminothiophenes Unobtainable via the Gewald Reaction." Journal of Organic Chemistry 86, no. 14 (July 1, 2021): 9418–27. http://dx.doi.org/10.1021/acs.joc.1c00740.

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47

Han, Ying, Wan-Quan Tang, and Chao-Guo Yan. "Gewald-type reaction of double activated 2,3-diarylcyclopropanes with elemental sulfur for synthesis of polysubstituted 2-aminothiophenes." Tetrahedron Letters 55, no. 8 (February 2014): 1441–43. http://dx.doi.org/10.1016/j.tetlet.2014.01.043.

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48

Mojtahedi, Mohammad M., M. Saeed Abaee, Peyman Mahmoodi, and Mehdi Adib. "ChemInform Abstract: Convenient Synthesis of 2-Aminothiophene Derivatives by Acceleration of Gewald Reaction under Ultrasonic Aqueous Conditions." ChemInform 41, no. 48 (November 4, 2010): no. http://dx.doi.org/10.1002/chin.201048090.

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49

Moeinpour, Farid, Raheleh Omidinia, Nadieh Dorostkar-Ahmadi, and Bentalhoda Khoshdeli. "ChemInform Abstract: Cesium Carbonate as a Heterogeneous Base Catalyst for Synthesis of 2-Aminothiophenes via Gewald Reaction." ChemInform 42, no. 42 (September 27, 2011): no. http://dx.doi.org/10.1002/chin.201142095.

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50

Wang, Dao-Lin, Jian-Ying Wu, and Qing-Tao Cui. "ChemInform Abstract: An Efficient One-Pot Synthesis of Thiophene-Fused Pyrido[3,2-a]azulenes via Gewald Reaction." ChemInform 46, no. 19 (April 23, 2015): no. http://dx.doi.org/10.1002/chin.201519214.

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