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Journal articles on the topic '2-aminothiophenes'

Author: Grafiati

Published: 4 June 2021

Last updated: 4 February 2022

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1

Kirsch, Gilbert, Ahmed Abdelwahab, and Atef Hanna. "Targeted Synthesis of 4-Chloro-3-formylthieno[2,3-b]pyridine and/or 4-Chlorothieno[2,3-b]pyridine by Reaction between N-Protected 3-Acetyl-2-aminothiophenes and Vilsmeier–Haack Reagent." Synthesis 49, no. 13 (2017): 2971–79. http://dx.doi.org/10.1055/s-0036-1588992.

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Formylated chlorothieno[2,3-b]pyridine derivatives were synthesized by reaction between N-protected 3-acetyl-2-aminothiophenes and Vilsmeier–Haack reagent under classical conditions. These products were not accessible without N-protection of the starting materials or by reaction between the reagent and 4-chlorothieno[2,3-b]pyridine under any conditions. The conditions of the reaction could be altered to produce unformylated derivatives in better yields than reaction with unprotected aminothiophene.

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2

Terrier, François, Marie-José Pouet, Khalid Gzouli, Jean-Claude Hallé, Francis Outurquin, and Claude Paulmier. "Carbon-carbon coupling of 4,6-dinitrobenzofuroxan with 3-aminothiophenes: a kinetic and structural study." Canadian Journal of Chemistry 76, no. 6 (1998): 937–45. http://dx.doi.org/10.1139/v98-079.

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Potentiometric measurements carried out in a 50-50 (v/v) H2O-Me2SO mixture together with 1H and 13C NMR studies carried out in pure Me2SO-d6 reveal that 3-aminothiophene (4a), 3-N-(methylamino)thiophene (4b), and 3-N,N-dimethylaminothiophene (4c) undergo protonation exclusively at the amino groups in dilute acid solutions. The pKa values of 4a, 4b, and 4c are equal to 3.38, 3.65, and 3.53, respectively, at 25°C, comparing well with those for related anilines in the same aqueous Me2SO mixtures. However, despite this similarity of the nitrogen basicities, compounds 4a, 4b, and 4c are found to be

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3

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

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4

Hallas, Geoffrey, and Andrew D. Towns. "Dyes derived from aminothiophenes—Part 2. Spectroscepic properties of some disperse dyes derived from 2-aminothiophenes." Dyes and Pigments 33, no. 3 (1997): 205–13. http://dx.doi.org/10.1016/s0143-7208(96)00047-2.

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5

Zeng, Fanxun, Pengjian Liu, Xusheng Shao, Zhong Li, and Xiaoyong Xu. "Catalyst-free and selective synthesis of 2-aminothiophenes and 2-amino-4,5-dihydrothiophenes from 4-thiazolidinones in water." RSC Advances 6, no. 64 (2016): 59808–15. http://dx.doi.org/10.1039/c6ra11151c.

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6

Virieux, David, Anne-Françoise Guillouzic, and Henri-Jean Cristau. "Triphenylphosphine catalyzed formation of functionalized 2-aminothiophenes." Heteroatom Chemistry 18, no. 3 (2007): 312–15. http://dx.doi.org/10.1002/hc.20300.

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7

Thanna, Sandeep, Susan E. Knudson, Anna Grzegorzewicz, et al. "Synthesis and evaluation of new 2-aminothiophenes against Mycobacterium tuberculosis." Organic & Biomolecular Chemistry 14, no. 25 (2016): 6119–33. http://dx.doi.org/10.1039/c6ob00821f.

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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 (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 (2010): no. http://dx.doi.org/10.1002/chin.199936290.

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10

Zhang, Xuxue, Chuan Liu, Yupian Deng та Song Cao. "Chemo- and regioselective synthesis of polysubstituted 2-aminothiophenes by the cyclization of gem-dibromo or gem-dichloroalkenes with β-keto tertiary thioamides". Organic & Biomolecular Chemistry 18, № 38 (2020): 7540–44. http://dx.doi.org/10.1039/d0ob01821j.

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A facile and practical method for the synthesis of 2,3,4-trisubstituted 2-aminothiophenes by the cyclization of gem-dibromoalkenes or gem-dichloroalkenes with β-keto tertiary thioamides has been developed.

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11

Irgashev, Roman A., Alexander S. Steparuk, and Gennady L. Rusinov. "One-pot synthesis of 2-substituted thieno[3,2-b]indoles from 3-aminothiophene-2-carboxylates through in situ generated 3-aminothiophenes." Tetrahedron Letters 60, no. 43 (2019): 151185. http://dx.doi.org/10.1016/j.tetlet.2019.151185.

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12

Hallas, Geoffrey, and Andrew D. Towns. "Dyes derived from aminothiophenes—Part 3. Application of some disperse dyes derived from 2-aminothiophenes to hydrophobic fibres." Dyes and Pigments 33, no. 3 (1997): 215–28. http://dx.doi.org/10.1016/s0143-7208(96)00049-6.

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13

Fondjo, Emmanuel Sopbué, and Dietrich Döpp. "Reactions of some annelated 2-aminothiophenes with two naphthoquinones." Arkivoc 2006, no. 15 (2006): 37–47. http://dx.doi.org/10.3998/ark.5550190.0007.f05.

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14

Aurelio, Luigi, Bernard L. Flynn, and Peter J. Scammells. "Reaction Pathways to 2-Aminothiophenes and Thiophene-3-carbonitriles." Australian Journal of Chemistry 62, no. 5 (2009): 402. http://dx.doi.org/10.1071/ch09004.

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Over the past two decades 2-amino-3-benzoylthiophenes have been found to act as allosteric enhancers of the adenosine A1 receptor (A1AR). As such, compounds of this type have potential applications in the therapy of a variety of disorders by enhancing A1AR activation. Initial studies in this field identified various 2-amino-3-benzoylthiophenes as potential leads and of these PD 81723 1a has become the benchmark for comparative studies due to its favourable ratio of allosteric enhancement to antagonism. Surprisingly the synthesis and characterization of PD 81723 1a has not been previously repor

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15

Peet, Norton P., Shyam Sunder, Robert J. Barbuch, and Anna P. Vinogradoff. "Mechanistic observations in the gewald syntheses of 2-aminothiophenes." Journal of Heterocyclic Chemistry 23, no. 1 (1986): 129–34. http://dx.doi.org/10.1002/jhet.5570230126.

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16

Puterova, Z., and A. Krutosikova. "ChemInform Abstract: Substituted 2-Aminothiophenes: Synthesis, Properties and Applications." ChemInform 42, no. 4 (2010): no. http://dx.doi.org/10.1002/chin.201104240.

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17

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

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18

Zhang, Haiqing, Guichun Yang, Jianian Chen, and Zuxing Chen. "Gewald synthesis of 2-aminothiophenes on a soluble polymer-support." Journal of Chemical Research 2004, no. 5 (2004): 360–61. http://dx.doi.org/10.3184/0308234041639665.

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19

Sopbué Fondjo, Emmanuel, Dietrich Döpp, and Gerald Henkel. "Reactions of some anellated 2-aminothiophenes with electron poor acetylenes." Tetrahedron 62, no. 29 (2006): 7121–31. http://dx.doi.org/10.1016/j.tet.2006.04.037.

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20

Yarovenko, Vladimir, Igor Shedishev, Aleksandr Dudnik, Igor Zavarin, and Michail Kraushkin. "Synthesis and Reactivity of 2-(1,2,3-Dithiazol-5- Ylidene)Aminothiophenes." Phosphorus, Sulfur, and Silicon and the Related Elements 185, no. 7 (2010): 1558–70. http://dx.doi.org/10.1080/10426500903127581.

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21

Aurelio, Luigi, Heidi Figler, Bernard L. Flynn, Joel Linden, and Peter J. Scammells. "5-Substituted 2-aminothiophenes as A1 adenosine receptor allosteric enhancers." Bioorganic & Medicinal Chemistry 16, no. 3 (2008): 1319–27. http://dx.doi.org/10.1016/j.bmc.2007.10.065.

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22

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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23

Katritzky, Alan R., Xiaojing Wang, and Anna Denisenko. "A Facile Synthesis of 3-Substituted-2-aminothiophenes and 1,3-Disubstituted-2-methylthiopyrroles." Journal of Organic Chemistry 66, no. 8 (2001): 2850–53. http://dx.doi.org/10.1021/jo001159x.

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24

Deniaud, David, Aélig Robin, and Jean-Claude Meslin. "2-Aminothiabutadiene as Useful Building Block in the Synthesis of 2-Aminothiopyrans and 2-Aminothiophenes." Synthesis 2004, no. 10 (2004): 1633–40. http://dx.doi.org/10.1055/s-2004-829112.

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25

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

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26

Fondjo, E. Sopbué, and D. Döpp. "Reactions of three [c]annelated 2-aminothiophenes with electron poor olefins." Arkivoc 2006, no. 10 (2006): 90–101. http://dx.doi.org/10.3998/ark.5550190.0007.a12.

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27

Shestopalov, A. M., and K. G. Nikishin. "Stereoselective method of synthesis of substituted trans-4,5-dihydro-2-aminothiophenes." Chemistry of Heterocyclic Compounds 34, no. 9 (1998): 1089–90. http://dx.doi.org/10.1007/bf02251559.

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28

Litvinov, V. P., Yu A. Sharanin, and F. S. Babichev. "Cyclization of Nitriles as Synthetic Route to 2-and 3-Aminothiophenes." Sulfur reports 6, no. 2 (1986): 97–128. http://dx.doi.org/10.1080/01961778608082495.

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29

Hesse, Stéphanie, Germain Revelant, Sandrine Dunand, and Gilbert Kirsch. "Microwave-Assisted Synthesis of 5-Substituted 2-Aminothiophenes Starting from Arylacetaldehydes." Synthesis 2011, no. 18 (2011): 2935–40. http://dx.doi.org/10.1055/s-0030-1261032.

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30

Hallas, G. "Synthesis and spectral properties of azo dyes derived from 2-aminothiophenes and 2-aminothiazoles." Dyes and Pigments 42, no. 3 (1999): 249–65. http://dx.doi.org/10.1016/s0143-7208(99)00031-5.

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31

Fondjo, E. Sopbué, and D. Döpp. "Corrigendum. Reactions of three [c]annelated 2-aminothiophenes with electron poor olefins." Arkivoc 2006, no. 10 (2006): 228–29. http://dx.doi.org/10.3998/ark.5550190.0007.a26.

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32

Zaragoza, Florencio. "Solid-phase synthesis of substituted 3-aminothiophenes and 2-methylene-2,3-dihydrothiazoles." Tetrahedron Letters 37, no. 34 (1996): 6213–16. http://dx.doi.org/10.1016/0040-4039(96)01326-3.

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33

Hwang, Jimin, Lydia Borgelt, and Peng Wu. "Multicomponent Petasis Reaction for the Synthesis of Functionalized 2-Aminothiophenes and Thienodiazepines." ACS Combinatorial Science 22, no. 10 (2020): 495–99. http://dx.doi.org/10.1021/acscombsci.0c00173.

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34

Tormyshev, Victor, Anthony Flinn, Dmitry Trukhin, Olga Rogozhnikova, Tatiana Mikhalina, and Tatiana Troitskaya. "Aryl Alkyl Ketones in a One-Pot Gewald Synthesis of 2-Aminothiophenes." Synlett 2006, no. 16 (2006): 2559–64. http://dx.doi.org/10.1055/s-2006-951484.

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35

Chekanova, L. G., K. O. Manylova, P. T. Pavlov, A. N. Vasyanin, S. N. Shurov, and O. A. Maiorova. "Physicochemical properties of 4,5-(aryl,alkyl)-3-substituted 2-aminothiophenes sulfonyl derivatives." Russian Journal of General Chemistry 87, no. 3 (2017): 414–19. http://dx.doi.org/10.1134/s1070363217030094.

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36

Fogue, Pythagore Soubgwi, Paul Keilah Lunga, Emmanuel Sopbué Fondjo, et al. "Substituted 2-aminothiophenes: antifungal activities and effect on Microsporum gypseum protein profile." Mycoses 55, no. 4 (2011): 310–17. http://dx.doi.org/10.1111/j.1439-0507.2011.02089.x.

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37

Guan, Xiao-Yang, and Min Shi. "PPh2Me-Mediated Tandem Reaction of 2-Alkyl-2,3-butadienoates with Isothiocyanates: Formation of 2-Aminothiophenes." ACS Catalysis 1, no. 10 (2011): 1154–57. http://dx.doi.org/10.1021/cs2003214.

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38

Katritzky, Alan R., Xiaojing Wang, and Anna Denisenko. "ChemInform Abstract: A Facile Synthesis of 3-Substituted-2-aminothiophenes and 1,3-Disubstituted-2-methylthiopyrroles." ChemInform 32, no. 36 (2010): no. http://dx.doi.org/10.1002/chin.200136042.

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39

Zhang, Xuxue, Mingsheng Wu, Juan Zhang та Song Cao. "Synthesis of N,N-disubstituted 2-aminothiophenes by the cyclization of gem-difluoroalkenes with β-keto thioamides". Organic & Biomolecular Chemistry 15, № 11 (2017): 2436–42. http://dx.doi.org/10.1039/c7ob00368d.

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40

Eckert, Katrin, Anke Schröder, and Horst Hartmann. "Preparation and Characterization of Cyanovinyl-Substituted 2-Aminothiophenes and 2-Aminothiazoles and Some of Their Heterooligomers." European Journal of Organic Chemistry 2000, no. 7 (2000): 1327–34. http://dx.doi.org/10.1002/1099-0690(200004)2000:7<1327::aid-ejoc1327>3.0.co;2-t.

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41

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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42

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 (2006): 1543–48. http://dx.doi.org/10.1080/00397910600588819.

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43

Revelant, Germain, Sandrine Dunand, Stephanie Hesse, and Gilbert Kirsch. "ChemInform Abstract: Microwave-Assisted Synthesis of 5-Substituted 2-Aminothiophenes Starting from Arylacetaldehydes." ChemInform 43, no. 3 (2011): no. http://dx.doi.org/10.1002/chin.201203087.

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44

Shestopalov, A. M., and K. G. Nikishin. "ChemInform Abstract: Stereoselective Method of Synthesis of Substituted trans-4,5-Dihydro-2-aminothiophenes." ChemInform 30, no. 14 (2010): no. http://dx.doi.org/10.1002/chin.199914135.

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45

Takahata, Hiroki, Keiko Moriyama, Mihoko Maruyama та Takao Yamazaki. "Novel synthesis of 2-aminothiophenes via iodoiminothiolactonization of γ,δ-unsaturated secondary thioamides". J. Chem. Soc., Chem. Commun., № 22 (1986): 1671. http://dx.doi.org/10.1039/c39860001671.

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46

Surikova, T. P., V. D. Zakharova, S. S. Mochalov, and Yu S. Shabarov. "Synthesis and nitration of some 4-cyclopropyl- and 4-(p-cyclopropylphenyl)-2-aminothiophenes." Chemistry of Heterocyclic Compounds 24, no. 8 (1988): 860–64. http://dx.doi.org/10.1007/bf00479336.

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47

Sensfuss, Ulrich, and Wolf D. Habicher. "2-aminothiophenes from triacetonamine: A convenient way to novel sterically hindered piperidine derivatives." Heteroatom Chemistry 9, no. 6 (1998): 529–36. http://dx.doi.org/10.1002/(sici)1098-1071(1998)9:6<529::aid-hc1>3.0.co;2-#.

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48

Thomas, Joice, Sampad Jana, Mahendra Sonawane, et al. "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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49

Batsyts, Sviatoslav, Maksym Shehedyn, Evgeny A. Goreshnik, Mykola D. Obushak, Andreas Schmidt, and Yurii V. Ostapiuk. "2-Bromo-2-chloro-3-arylpropanenitriles as C-3 Synthons for the Synthesis of Functionalized 3-Aminothiophenes." European Journal of Organic Chemistry 2019, no. 48 (2019): 7842–56. http://dx.doi.org/10.1002/ejoc.201901512.

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50

Kanitz, Andreas, Jörg Schumann, Marcus Scheffel, et al. "Arylated Mono- and Bifunctional 2-Aminothiophenes and 2-Aminothiazoles as a New Class of Hole Transport Materials." Chemistry Letters 31, no. 9 (2002): 896–97. http://dx.doi.org/10.1246/cl.2002.896.

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