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Journal articles on the topic 'Imidazole-2-thiones'

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Published: 4 June 2021
Last updated: 15 February 2022

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1

Koner, Abhishek, Spencer C. Serin, Gregor Schnakenburg, Brian O. Patrick, Derek P. Gates, and Rainer Streubel. "Exploring the chemistry of backbone amino(chloro)phosphanyl-substituted imidazole-2-thiones." Dalton Transactions 46, no. 31 (2017): 10504–14. http://dx.doi.org/10.1039/c7dt01859b.

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2

Majhi, Paresh Kumar, Gregor Schnakenburg, Anthony J. Arduengo, and Rainer Streubel. "Synthesis and Oxidative Desulfurization of PV-Functionalized Imidazole-2-thiones: Easy Access to P-Functional Ionic Liquids." Australian Journal of Chemistry 68, no. 8 (2015): 1282. http://dx.doi.org/10.1071/ch14726.

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Selective synthesis of 4-phosphanylated imidazole-2-thiones 2d, 3a,b(b′),c(c′),d were achieved using a backbone lithiation and phosphanylation reaction protocol. The 4-phosphanylated-imidazole-2-thiones 3b(b′),c(c′) were subjected to a oxidation/phosphanylation/oxidation reaction sequence to access C4/5-bis(phosphanoyl)-substituted imidazole-2-thiones 7b,c. Oxidative desulfurization of phosphanylated imidazole-2-thiones 2d, 4a,d, and 7b,c with hydrogen peroxide afforded the first examples of room temperature imidazolium ionic liquids 8d, 9a,d, and 10b,c respectively, possessing backbone P-subs
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3

Koner, Abhishek, Gregor Pfeifer, Zsolt Kelemen, et al. "1,4-Diphosphinines from Imidazole-2-thiones." Angewandte Chemie International Edition 56, no. 31 (2017): 9231–35. http://dx.doi.org/10.1002/anie.201704070.

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4

Trzhtsinskaya, Bella V., and Nina D. Abramova. "Imidazole-2-Thiones: Synthesis, Structure, Properties." Sulfur reports 10, no. 4 (1991): 389–421. http://dx.doi.org/10.1080/01961779108048760.

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5

Po, Henry N., Zarila Shariff, Jeffrey A. Masse, Fillmore Freeman, and Monica C. Keindl-yu. "THERMODYNAMIC AND ELECTROCHEMICAL PROPERTIES OF IMIDAZOLE-2-THIOLS (IMIDAZOLE-2(3H)-THIONES)." Phosphorus, Sulfur, and Silicon and the Related Elements 63, no. 1-2 (1991): 1–12. http://dx.doi.org/10.1080/10426509108029421.

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6

Batanero, Belén. "Electrosynthesis of N-Substituted Imidazole-2-thiones." Synthesis 1999, no. 10 (1999): 1809–13. http://dx.doi.org/10.1055/s-1999-3585.

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7

Mlostoń, Grzegorz, Małgorzata Celeda, Marcin Jasiński, et al. "2-Unsubstituted Imidazole N-Oxides as Novel Precursors of Chiral 3-Alkoxyimidazol-2-ylidenes Derived from trans-1,2-Diaminocyclohexane and Other Chiral Amino Compounds." Molecules 24, no. 23 (2019): 4398. http://dx.doi.org/10.3390/molecules24234398.

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‘Desymmetrization’ of trans-1,2-diaminocyclohexane by treatment with α,ω-dihalogenated alkylation reagents leads to mono-NH2 derivatives (‘primary-tertiary diamines’). Upon reaction with formaldehyde, these products formed monomeric formaldimines. Subsequently, reactions of the formaldimines with α-hydroxyiminoketones led to the corresponding 2-unsubstituted imidazole N-oxide derivatives, which were used here as new substrates for the in situ generation of chiral imidazol-2-ylidenes. Upon O-selective benzylation, new chiral imidazolium salts were obtained, which were deprotonated by treatment
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8

TRZHTSINSKAYA, B. V., and N. D. ABRAMOVA. "ChemInform Abstract: Imidazole-2-thiones: Synthesis, Structure, Properties." ChemInform 22, no. 51 (2010): no. http://dx.doi.org/10.1002/chin.199151344.

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9

Abramov, N. D., and B. V. Trzhtsinskaya. "Structure and properties of imidazole-2-thiones (review)." Chemistry of Heterocyclic Compounds 24, no. 12 (1988): 1309–21. http://dx.doi.org/10.1007/bf00486668.

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10

Wang, Xi-Cun, Fang Wang, Zheng-Jun Quan, Man-Gang Wang, and Zheng Li. "An efficient and clean synthesis of 1-aroyl-3-aryl-4-substituted imidazole-2-thiones in water." Journal of Chemical Research 2005, no. 11 (2005): 689–90. http://dx.doi.org/10.3184/030823405774909423.

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Treatment 1-aryl-3-aroyl/benzofuroyl thioureas with α-bromo substituted carbonyl compounds in water affording 1-aroyl/benzofuroyl-3-aryl-4-substituted imidazole-2-thiones in excellent yields within short time.
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11

Mloston, Grzegorz, and Marcin Jasiński. "Synthesis and selected transformations of 3-oxido-1H-imidazole-4-carboxamides." Collection of Czechoslovak Chemical Communications 75, no. 8 (2010): 871–85. http://dx.doi.org/10.1135/cccc2010012.

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An efficient synthesis of new N-alkyl- and N-aryl-3-oxido-1H-imidazole-4-carboxamides based on exploration of inexpensive, commercially available ethyl acetoacetate, paraformaldehyde and primary amines is described. Representative compounds were tested in selected transformations, such as ‘sulfur-transfer reaction’ leading to imidazole-2-thiones and isomerization to corresponding imidazol-2-ones. Strong intramolecular hydrogen bonding via the N-oxide function results in the reduced reactivity of 3-oxido-1H-imidazole-4-carboxamides in both reactions. Moreover, the palladium catalyzed C(2)-aryla
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12

PO, H. N., Z. SHARIFF, J. A. MASSE, F. FREEMAN, and M. C. KEINDL-YU. "ChemInform Abstract: Thermodynamic and Electrochemical Properties of Imidazole-2-thiols (I) (Imidazole-2(3H)-thiones)." ChemInform 23, no. 7 (2010): no. http://dx.doi.org/10.1002/chin.199207067.

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13

Suszka, Andrzej. "Charge-transfer complexes of imidazole-2-thiones with iodine." Journal of the Chemical Society, Perkin Transactions 2, no. 4 (1985): 531. http://dx.doi.org/10.1039/p29850000531.

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14

Batanero, Belen, Jose Escudero, and Fructuoso Barba. "ChemInform Abstract: Electrosynthesis of N-Substituted Imidazole-2-thiones." ChemInform 31, no. 2 (2010): no. http://dx.doi.org/10.1002/chin.200002150.

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15

Bark, Lionel S., Norma Chadwick, and Otto Meth-Cohn. "The synthesis and ligand properties of N,N′-Polymethylene - bridged imidazole-2-thiones and benzimidazole-2-thiones." Tetrahedron 48, no. 37 (1992): 7863–68. http://dx.doi.org/10.1016/s0040-4020(01)80463-4.

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16

KUHN, N., and T. KRATZ. "ChemInform Abstract: Imidazole Chemistry. Part 2. Synthesis of Imidazol-2-ylidenes by Reduction of Imidazole-2(3H)-thiones." ChemInform 24, no. 50 (2010): no. http://dx.doi.org/10.1002/chin.199350199.

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17

Egorov, D. M., Yu L. Piterskaya, and A. V. Dogadina. "Reaction of chloroethynylphosphonates with 1-methyl-3H-imidazole-2-thiones." Russian Journal of General Chemistry 85, no. 2 (2015): 502–4. http://dx.doi.org/10.1134/s1070363215020255.

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18

Egorov, D. M., Yu L. Piterskaya, V. F. Mironov, and A. V. Dogadina. "Reactions of chloroethynylphosphonates with 4,5-substituted 1H-imidazole-2-thiones." Russian Journal of General Chemistry 85, no. 9 (2015): 2203–5. http://dx.doi.org/10.1134/s1070363215090273.

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19

Mlostoń, Grzegorz, and Heinz Heimgartner. "Unexpected Insertion Reaction of Dimethoxycarbene with Imidazole-2(3H)-thiones." Phosphorus, Sulfur, and Silicon and the Related Elements 185, no. 5-6 (2010): 1235–42. http://dx.doi.org/10.1080/10426501003773761.

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20

Cert, Arturo, and Mariana Trujillo Péerez-Lanzac. "Mass spectrometry of substituted 1,3-dihydro-2H-imidazole-2-thiones." Organic Mass Spectrometry 22, no. 4 (1987): 203–9. http://dx.doi.org/10.1002/oms.1210220405.

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21

Trzhtsinskaya, B. V., A. E. Aleksandrova, N. D. Abramova, L. V. Andriyankova, T. I. Vinogradova, and R. A. Shchegoleva. "Synthesis and tuberculostatic activity of derivatives of imidazole-2-thiones." Pharmaceutical Chemistry Journal 26, no. 4 (1992): 346–49. http://dx.doi.org/10.1007/bf00773168.

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22

Kuhn, Norbert, and Thomas Kratz. "Synthesis of Imidazol-2-ylidenes by Reduction of Imidazole-2(3H)-thiones." Synthesis 1993, no. 06 (1993): 561–62. http://dx.doi.org/10.1055/s-1993-25902.

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23

Abu Almaaty, Ali H., Eslam E. M. Toson, El-Sherbiny H. El-Sayed, et al. "5-Aryl-1-Arylideneamino-1H-Imidazole-2(3H)-Thiones: Synthesis and In Vitro Anticancer Evaluation." Molecules 26, no. 6 (2021): 1706. http://dx.doi.org/10.3390/molecules26061706.

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A novel series of N-1 arylidene amino imidazole-2-thiones were synthesized, identified using IR, 1H-NMR, and 13C-NMR spectral data. Cytotoxic effect of the prepared compounds was carried out utilizing three cancer cell lines; MCF-7 breast cancer, HepG2 liver cancer, and HCT-116 colon cancer cell lines. Imidazole derivative 5 was the most potent of all against three cell lines. DNA flow cytometric analysis showed that, imidazoles 4d and 5 exhibit pre-G1 apoptosis and cell cycle arrest at G2/M phase. The results of the VEGFR-2 and B-Raf kinase inhibition assay revealed that compounds 4d and 5 di
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24

Mageed, Ahmed H., Brian W. Skelton, Alexandre N. Sobolev, and Murray V. Baker. "Exploring structural and conformational behaviour of cyclophanes incorporating imidazole-2-thiones." Tetrahedron 74, no. 24 (2018): 2956–66. http://dx.doi.org/10.1016/j.tet.2018.04.074.

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25

Xu, J., and J. C. Yadan. "A New and Convenient Synthesis of Imidazole-2-thiones from Imidazoles." Synlett 1995, no. 03 (1995): 239–41. http://dx.doi.org/10.1055/s-1995-4931.

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26

M. Lagoja, Joachim G. Schantl, Irene. "Direct Synthetic Approach to N– Aminoimidazole–2–thiones and Imidazole Derivatives." Molecules 1, no. 9 (1997): 116–18. http://dx.doi.org/10.1007/s007830050020.

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27

Mlostoń, Grzegorz, Małgorzata Celeda, Katarzyna Urbaniak, et al. "Synthesis and selected transformations of 2-unsubstituted 1-(adamantyloxy)imidazole 3-oxides: straightforward access to non-symmetric 1,3-dialkoxyimidazolium salts." Beilstein Journal of Organic Chemistry 15 (February 19, 2019): 497–505. http://dx.doi.org/10.3762/bjoc.15.43.

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Adamantyloxyamine reacts with formaldehyde to give N-(adamantyloxy)formaldimine as a room-temperature-stable compound that exists in solution in monomeric form. This product was used for reactions with α-hydroxyiminoketones leading to a new class of 2-unsubstituted imidazole 3-oxides bearing the adamantyloxy substituent at N(1). Their reactions with 2,2,4,4-tetramethylcyclobutane-1,3-dithione or with acetic acid anhydride occurred analogously to those of 1-alkylimidazole 3-oxides to give imidazol-2-thiones and imidazol-2-ones, respectively. Treatment of 1-(adamantyloxy)imidazole 3-oxides with
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28

Frank, Priya V., Mahesha Manjunatha Poojary, Naral Damodara, and Chandrashekhar Chikkanna. "Synthesis and antimicrobial studies of some Mannich bases carrying imidazole moiety." Acta Pharmaceutica 63, no. 2 (2013): 231–39. http://dx.doi.org/10.2478/acph-2013-0016.

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3 Starting from 2-methyl-4-nitro-imidazole, new 5-(2-methyl- 4-nitro-1-imidazomethyl)-1,3,4-oxadiazole-2-thione () was synthesized and was subjected to Mannich reaction with appropriate amines to yield a new series of 3-substituted aminomethyl-5-(2-methyl-4-nitro-1-imidazomethyl)- 1,3,4-oxadiazole-2-thiones (4a-j). The structure of the title compounds was elucidated by elemental analysis and spectral data. The newly synthesized Mannich bases were screened for their antibacterial and antifungal activity. Many of these compounds exhibited potent antifungal activity.
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29

Majhi, Paresh Kumar, Susanne Sauerbrey, Alexander Leiendecker, Gregor Schnakenburg, Anthony J. Arduengo III, and Rainer Streubel. "Synthesis and first complexes of C4/5 P-bifunctional imidazole-2-thiones." Dalton Transactions 42, no. 36 (2013): 13126. http://dx.doi.org/10.1039/c3dt51557e.

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30

Sauerbrey, Susanne, Paresh Kumar Majhi, Gregor Schnakenburg, Anthony J. Arduengo III, and Rainer Streubel. "Synthesis, structure and reactivity of 4-phosphanylated 1,3-dialkyl-imidazole-2-thiones." Dalton Transactions 41, no. 17 (2012): 5368. http://dx.doi.org/10.1039/c2dt12483a.

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31

Karpov, M. V., A. N. Belyaev, D. D. Orlova, P. B. Davidovich, and A. V. Garabadzhiu. "Reaction of tert-butylimine of phenylpropiolic aldehyde with substituted imidazole-2-thiones." Russian Journal of General Chemistry 85, no. 3 (2015): 766–67. http://dx.doi.org/10.1134/s1070363215030391.

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32

Feroci, Marta, Monica Orsini, and Achille Inesi. "An Efficient Combined Electrochemical and Ultrasound Assisted Synthesis of Imidazole-2-Thiones." Advanced Synthesis & Catalysis 351, no. 13 (2009): 2067–70. http://dx.doi.org/10.1002/adsc.200900359.

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33

Zeng, Run-Sheng, Jian-Ping Zou, San-Jun Zhi, Jun Chen, and Qi Shen. "Novel Synthesis of 1-Aroyl-3-aryl-4-substituted Imidazole-2-thiones." Organic Letters 5, no. 10 (2003): 1657–59. http://dx.doi.org/10.1021/ol030024l.

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34

Ross, Stephen T., Lawrence I. Kruse, Eliot H. Ohlstein, et al. "Inhibitors of dopamine .beta.-hydroxylase. 3. Some 1-(pyridylmethyl)imidazole-2-thiones." Journal of Medicinal Chemistry 30, no. 8 (1987): 1309–13. http://dx.doi.org/10.1021/jm00391a008.

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35

Mlostoń, Grzegorz, Małgorzata Celeda, Wiktor Poper, et al. "Synthesis, Selected Transformations, and Biological Activity of Alkoxy Analogues of Lepidilines A and C." Materials 13, no. 18 (2020): 4190. http://dx.doi.org/10.3390/ma13184190.

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Condensation of diacetyl monooxime with formaldimines derived from alkoxyamines in glacial acetic acid at room temperature leads to corresponding 2-unsubstituted imidazole N-oxides bearing an alkoxy substituent at the N(1) atom of the imidazole ring. Subsequent O-benzylation afforded, depending on the type of alkylating agent, either symmetric or nonsymmetric alkoxyimidazolium salts considered as structural analogues of naturally occurring imidazole alkaloids, lepidilines A and C. Some of the obtained salts were tested as precursors of nucleophilic heterocyclic carbenes (NHCs), which in situ r
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36

Shaker, Mohammad. "A Facile Procedure for Synthesis of Several 1, 4, 5-Trisubstituted-1Himidazole- 2(3H)-ones and -thiones via a One-pot Three-portion Reaction in Solvent and Microwave Irradiation." Letters in Organic Chemistry 16, no. 2 (2019): 104–9. http://dx.doi.org/10.2174/1570178615666180522101532.

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An ordinary procedure for the synthesis of several 1, 4, 5-trisubstituted-1H-imidazole- 2(3H)-ones and -thiones by a one-pot three-component reaction of glacial acetic acid under solvent, microwave irradiation condition is proposed. The products were formed through cyclization of benzoin with isothiocyanates or isocyanates and ammonium acetate. All incorporated combinations were determined for their spectral and microanalytical information. These compounds were subsequently studied for their fluorescence properties.
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37

Bossio, Ricardo, Stefano Marcaccini, Roberto Pepino, Cecilia Polo, Tom� Torroba, and Giovanni Valle. "Synthesis of 1-Arylthiocarbonyl-4-isopropylamino-2,5-dihydro-1H-imidazole-2-thiones, a Novel Class of Imidazole Derivatives." HETEROCYCLES 29, no. 9 (1989): 1843. http://dx.doi.org/10.3987/com-89-5089.

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38

Markwalder, Jay, Richard Pottorf та Steven Seitz. "One-Pot Conversion of α-Thioureido Esters to Imidazol-2-ones and Imidazole-2-thiones". Synlett 1997, Sup. I (1997): 521–22. http://dx.doi.org/10.1055/s-1997-6138.

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39

XU, J., and J. C. YADAN. "ChemInform Abstract: A New and Convenient Synthesis of Imidazole-2-thiones from Imidazoles." ChemInform 26, no. 32 (2010): no. http://dx.doi.org/10.1002/chin.199532157.

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40

Azap, Cengiz, Anna Christoffers, and Renat Kadyrov. "Scalable Synthesis of 1,3,4,5-Tetraaryl Imidazolium Salts as Precursors of Sterically Demanding N-Heterocyclic Carbenes." SynOpen 04, no. 01 (2020): 01–11. http://dx.doi.org/10.1055/s-0039-1690338.

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A convenient, large-scale, and cost-efficient synthesis of 4,5-diarylsubstituted N,N-diarylimidazolium salts is described. A variety of 1,3,4,5-tetraaryl imidazolium salts with increasing electron donation and steric bulk of the N-aryl groups was synthesized in good yields. In the key step, readily available N,N′-diarylthioureas and benzoin/anisoin are coupled to give imidazole-2-thiones, followed by imidazolium salt formation by oxidative desulfurization. In this way, N,N-diarylimidazolium salts with 2-methoxy, 2-methyl, and 2-isopropyl substituents could be obtained; the synthesis of their 2
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41

G. Schantl, Joachim, and Irene M. Lagoja. "Direct Synthetic Approach to N-Substituted 1-Amino-2,3-dihydro-1H-imidazole-2-thiones." HETEROCYCLES 45, no. 4 (1997): 691. http://dx.doi.org/10.3987/com-96-7715.

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42

Arduengo, Anthony J., John R. Moran, J. Rodriguez-Parada, and Michael D. Ward. "Molecular control of self-assembled monolayer films of imidazole-2-thiones: adsorption and reactivity." Journal of the American Chemical Society 112, no. 16 (1990): 6153–54. http://dx.doi.org/10.1021/ja00172a055.

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43

Suszka, Andrzej. "Charge-transfer complexes of imidazole-2-thiones and N,N′-dialkylthioureas with sulphur dioxide." J. Chem. Soc., Perkin Trans. 2, no. 9 (1989): 1327–33. http://dx.doi.org/10.1039/p29890001327.

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44

McCarthy, James R., Donald P. Matthews, Robert J. Broersma, et al. "1-(Thienylalkyl)imidazole-2(3H)-thiones as potent competitive inhibitors of dopamine .beta.-hydroxylase." Journal of Medicinal Chemistry 33, no. 7 (1990): 1866–73. http://dx.doi.org/10.1021/jm00169a006.

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45

BARK, L. S., N. CHADWICK, and O. METH-COHN. "ChemInform Abstract: N-Bridged Heterocycles. Part 6. The Synthesis and Ligand Properties of N,N′-Polymethylene-Bridged Imidazole-2-thiones and Benzimidazole-2- thiones." ChemInform 23, no. 52 (2010): no. http://dx.doi.org/10.1002/chin.199252179.

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46

Gašparová, Renáta, Martin Moncman, and Branislav Horváth. "Microwave assisted reactions of 2-[3-(Trifluoromethyl)phenyl]-4-R1-furo[3,2-b] pyrrole-5-carboxhydrazides." Open Chemistry 6, no. 2 (2008): 180–87. http://dx.doi.org/10.2478/s11532-008-0009-4.

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AbstractThe effect of microwave irradiation on the reactions of 2-[3-(trifluoromethyl)phenyl]-4-R1-furo[3,2-b]pyrrole-5-carboxhydrazides 1 with 5-arylfuran-2-carboxaldehydes 2, thiophene-2-carboxaldehyde (3) and methyl 2-formylfuro[3,2-b]pyrrole-5-carboxylates 4 has been studied. Reactions of 1 with formic and acetic acid, respectively, led to acylhydrazides 9a–c. Reaction of 1a with 4-substituted 1,3-oxazol-5(4H)-one 10 led to imidazole derivative 13. 1,2,4-Triazole-3-thiones 15a,b were synthesized by two-step reaction of 1a with potassium isothiocyanate and phenyl isothiocyanate, respectivel
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47

Shen, Shu-Su, Mao-Yi Lei, Yun-Xuan Wong, et al. "Intramolecular nucleophilic substitution at an sp2 carbon: synthesis of substituted thiazoles and imidazole-2-thiones." Tetrahedron Letters 50, no. 26 (2009): 3161–63. http://dx.doi.org/10.1016/j.tetlet.2008.12.118.

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48

SCHANTL, J. G., and I. M. LAGOJA. "ChemInform Abstract: Direct Synthetic Approach to N-Substituted 1-Amino-2,3-dihydro-1H- imidazole-2-thiones." ChemInform 28, no. 41 (2010): no. http://dx.doi.org/10.1002/chin.199741157.

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49

MCCARTHY, J. R., D. P. MATTHEWS, R. J. BROERSMA та ін. "ChemInform Abstract: 1-(Thienylalkyl)imidazole-2(3H)-thiones as Potent Competitive Inhibitors of Dopamine β-Hydroxylase." ChemInform 22, № 15 (2010): no. http://dx.doi.org/10.1002/chin.199115166.

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50

Chen, En, Jiaan Shao, Pai Tang, Ke Shu, Wenteng Chen, and Yongping Yu. "Catalyst-free three-component sequencing for efficient assembly of [1,3] oxazine N-fused imidazole-2-thiones." Green Chemistry 20, no. 16 (2018): 3696–99. http://dx.doi.org/10.1039/c8gc01766b.

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