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Journal articles on the topic 'Dieckmann condensation'

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Published: 4 June 2021
Last updated: 1 February 2022

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1

Maklad, Noha S. "ChemInform Abstract: Dieckmann Condensation." ChemInform 42, no. 18 (April 7, 2011): no. http://dx.doi.org/10.1002/chin.201118225.

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2

Pátek, Marcel. "Titanium-mediated Dieckmann condensation." Collection of Czechoslovak Chemical Communications 55, no. 5 (1990): 1223–27. http://dx.doi.org/10.1135/cccc19901223.

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The Dieckmann condensation of alkyl 2-(N-methyl-N-(alkoxycarbonylmethyl)sulfamoyl)-benzoates Ia and Ib with titanium tetrachloride-tert-amine or butyltitanium ate complex III affords alkyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxides IIa and IIb which are the piroxicam intermediates.
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3

Sieburth, Scott McN, and Chien-An Chen. "Tandem Asymmetric Alkylation-Dieckmann Condensation." Synlett 1995, no. 09 (September 1995): 928–30. http://dx.doi.org/10.1055/s-1995-5131.

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4

Nishimura, Tamiki, Makoto Sunagawa, Toshiya Okajima, and Yoshimasa Fukazawa. "Transition structures for the dieckmann condensation." Tetrahedron Letters 38, no. 40 (October 1997): 7063–66. http://dx.doi.org/10.1016/s0040-4039(97)01649-3.

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5

SIEBURTH, S. M., and C. A. CHEN. "ChemInform Abstract: Tandem Asymmetric Alkylation-Dieckmann Condensation." ChemInform 27, no. 3 (August 12, 2010): no. http://dx.doi.org/10.1002/chin.199603179.

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6

Pátek, Marcel, and František Hampl. "Conditions of the Dieckmann condensation of alkyl 2-(N-methyl-N-(alkoxycarbonylmethyl)sulfamoyl)benzoates." Collection of Czechoslovak Chemical Communications 54, no. 12 (1989): 3267–77. http://dx.doi.org/10.1135/cccc19893267.

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The Dieckmann condensation of alkyl 2-(N-methyl-N-(alkoxycarbonylmethyl)sulfamoyl)benzoates IIIa-IIIe with various bases affords alkyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxides IVa-IVe which are intermediates in the synthesis of antiinflammatory drug piroxicam. The yields of benzothiazines IVa-IVe depend mostly on the nature of a base, reaction temperature and solvent used for these condensations. Hitherto undescribed esters IIIb-IIIe were synthesized and their structures were confirmed by 1H and 13C NMR, and mass spectra.
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7

Böhme, Roswitha, Günther Jung, and Eberhard Breitmaier. "Synthesis of the Antibiotic (R)-Reutericyclinvia Dieckmann Condensation." Helvetica Chimica Acta 88, no. 11 (November 2005): 2837–41. http://dx.doi.org/10.1002/hlca.200590226.

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8

Chande, Madhukar S., Rahul R. Khanwelkar, and Pravin A. Barve. "Synthesis of Novel Spiro Compounds using Anthrone and Pyrazole-5-thione Moieties: A Michael Addition approach." Journal of Chemical Research 2007, no. 8 (August 2007): 468–71. http://dx.doi.org/10.3184/030823407x237821.

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Novel routes for the synthesis of spiro derivatives anthrone have been designed using a Michael addition reaction followed by a Dieckmann condensation and Thorpe–Ziegler cyclisation. Bis-Michael addition of pyrazole-5-thione with 1,5-diarylpenta-1,4-dien-3-one gave directly a spiro derivative of pyrazole-5-thione. An enol lactone was synthesised by using mono Michael addition on dimedone, followed by hydrolysis and condensation.
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9

Lei, Jie, Gui-Ting Song, Ya-Fei Luo, Dian-Yong Tang, Wei Yan, Hong-yu Li, Zhong-Zhu Chen, and Zhi-Gang Xu. "Synthesis of indoline-piperidinones via a novel Ugi, ring expansion, pseudo-Dieckmann condensation and rearrangement cascade reaction." Organic Chemistry Frontiers 7, no. 5 (2020): 737–41. http://dx.doi.org/10.1039/d0qo00028k.

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10

Iskakova, M. M., I. M. Biktagirov, L. Kh Faizullina, Sh M. Salikhov, M. G. Safarov, and F. A. Valeev. "Regiocontrolled dieckmann condensation of 3,4-Bis(methoxycarbonylmethyl) levoglucosenone derivative." Russian Journal of Organic Chemistry 50, no. 1 (January 2014): 105–9. http://dx.doi.org/10.1134/s1070428014010205.

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11

Raftery, Mark J., and John H. Bowie. "Does the dieckmann condensation occur in the gas phase?" Organic Mass Spectrometry 23, no. 10 (October 1988): 719–22. http://dx.doi.org/10.1002/oms.1210231008.

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12

Tanabe, Yoo, Atsushi Makita, Syunsuke Funakoshi, Ryota Hamasaki, and Tetsuo Kawakusu. "Practical Synthesis of (Z)-Civetone Utilizing Ti-Dieckmann Condensation." Advanced Synthesis & Catalysis 344, no. 5 (July 2002): 507. http://dx.doi.org/10.1002/1615-4169(200207)344:5<507::aid-adsc507>3.0.co;2-u.

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13

Nikulin, V. I., and L. M. Pisarenko. "Dieckmann-Shapiro condensation of substituted phthalides with p-dimethylaminobenzaldehyde." Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 35, no. 8 (August 1986): 1680–84. http://dx.doi.org/10.1007/bf00954613.

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14

Chande, Madhukar S., and Vijay Suryanarayan. "Synthesis of Spirocyclohexanone Ring Containing Thiazolidine Nucleus: A Regioselective Approach." Journal of Chemical Research 2005, no. 6 (June 2005): 345–47. http://dx.doi.org/10.3184/0308234054506749.

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The paper highlights the Michael addition reactions of 2-arylimino-3-aryl-thiazolidin-4-one 1 with acceptors like methyl acrylate and acrylonitrile to furnish the diadducts 5 and 8. Dieckmann condensation of 5 affords the spirocyclohexanone derivative. Also discussed is the interaction of 1 with 1,5-diarylpenta-1,4-dien-3-ones 9.
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15

Nadal, Brice, Julien Rouleau, Hélène Besnard, Pierre Thuéry, and Thierry Le Gall. "Synthesis of pulvinones via tandem Dieckmann condensation–alkoxide β-elimination." Tetrahedron 67, no. 14 (April 2011): 2605–11. http://dx.doi.org/10.1016/j.tet.2011.02.011.

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16

Fominova, Kateryna, Taras Diachuk, Iryna V. Sadkova, and Pavel K. Mykhailiuk. "Synthesis of 2,2-Disubstituted Spirocyclic Pyrrolidines by Intramolecular Dieckmann Condensation." European Journal of Organic Chemistry 2019, no. 22 (March 4, 2019): 3553–59. http://dx.doi.org/10.1002/ejoc.201801750.

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17

Toda, Fumio, Takaaki Suzuki, and Satoru Higa. "Solvent-free Dieckmann condensation reactions of diethyl adipate and pimelate." Journal of the Chemical Society, Perkin Transactions 1, no. 21 (1998): 3521–22. http://dx.doi.org/10.1039/a805884i.

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18

Le Gall, Thierry, Sophie Thetiot-Laurent, and Brice Nadal. "Synthesis of Bis(tetronic acid)s via Double Dieckmann Condensation." Synthesis 2010, no. 10 (April 15, 2010): 1697–701. http://dx.doi.org/10.1055/s-0029-1218738.

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19

Kulkarni, Bheemashankar A., and Arasu Ganesan. "Ion-Exchange Resins for Combinatorial Synthesis: 2,4-Pyrrolidinediones by Dieckmann Condensation." Angewandte Chemie International Edition in English 36, no. 22 (December 1, 1997): 2454–55. http://dx.doi.org/10.1002/anie.199724541.

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20

Svoboda, Jiří, Miloslav Nič, and Jaroslav Paleček. "Application of Magnesium Alkoxides to Syntheses of Benzoheterocyclic Compounds." Collection of Czechoslovak Chemical Communications 58, no. 3 (1993): 592–99. http://dx.doi.org/10.1135/cccc19930592.

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The Dieckmann condensation of methyl [(2-methoxycarbonyl)phenyl]-X-acetates Ia-Ih (X = O, S, SO2, NH, NCH3) initiated by action of magnesium methoxide, ethoxide, isopropoxide and other basic reagents have been studied under various conditions. Whereas magnesium methoxide has comparable efficiency as sodium methoxide and potassium tert-butoxide in syntheses of benzoheterocyclic compounds IIa-IIh, magnesium ethoxide gives the ethyl ester IIb in medium yield, and magnesium isopropoxide is quite inefficient in the condensation reaction. The alkylation of the esters IIa, IId, and IIg with methyl chloroacetate in the presence of sodium hydride in dimethylformamide gives the diesters IIi - IIk which on action by potassium tert-butoxide undergo the cyclization reaction to give esters III.
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21

Cogan, Dillon P., Joseph Ly, and Satish K. Nair. "Structural Basis for Enzymatic Off-Loading of Hybrid Polyketides by Dieckmann Condensation." ACS Chemical Biology 15, no. 10 (October 5, 2020): 2783–91. http://dx.doi.org/10.1021/acschembio.0c00579.

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22

Chande, Madhukar S., C. Sajithkumar, Hemant S. Mondkar, Pravin A. Barve, and Sachin Diwan. "Novel synthesis of 1,2,4-triazolophanes and 1,3,4-oxadiazolophanes: A dieckmann condensation approach." Journal of Heterocyclic Chemistry 49, no. 2 (December 19, 2011): 329–35. http://dx.doi.org/10.1002/jhet.729.

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23

Toda, Fumio, Takaaki Suzuki, and Satoru Higa. "ChemInform Abstract: Solvent-Free Dieckmann Condensation Reactions of Diethyl Adipate and Pimelate." ChemInform 30, no. 12 (June 17, 2010): no. http://dx.doi.org/10.1002/chin.199912054.

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24

Thetiot-Laurent, Sophie A. L., Brice Nadal, and Thierry Le Gall. "ChemInform Abstract: Synthesis of Bis(tetronic acid)s via Double Dieckmann Condensation." ChemInform 41, no. 40 (September 9, 2010): no. http://dx.doi.org/10.1002/chin.201040091.

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25

Ukrainets, I. V., S. G. Taran, P. A. Bezuglyi, and O. A. Evtifeeva. "4-Hydroxy-2-quinolones. 17. Dieckmann condensation as a thermally activated process." Chemistry of Heterocyclic Compounds 29, no. 9 (September 1993): 1041–43. http://dx.doi.org/10.1007/bf00534389.

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26

Nadal, Brice, Julien Rouleau, Helene Besnard, Pierre Thuery, and Thierry Le Gall. "ChemInform Abstract: Synthesis of Pulvinones via Tandem Dieckmann Condensation-Alkoxide β-Elimination." ChemInform 42, no. 33 (July 22, 2011): no. http://dx.doi.org/10.1002/chin.201133209.

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27

Bunce, Richard A., and Christina R. Harris. "Six-membered cyclic .beta.-keto esters by tandem conjugate addition-Dieckmann condensation reactions." Journal of Organic Chemistry 57, no. 25 (December 1992): 6981–85. http://dx.doi.org/10.1021/jo00051a058.

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28

Horta, Javier E. "Simple Microwave-Assisted Claisen and Dieckmann Condensation Experiments for the Undergraduate Organic Chemistry Laboratory." Journal of Chemical Education 88, no. 7 (July 2011): 1014–15. http://dx.doi.org/10.1021/ed1000944.

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29

Tanabe, Yoo, Naoki Manta, Ryohei Nagase, Tomoniri Misaki, Yoshinori Nishii, Makoto Sunagawa, and Akira Sasaki. "Practical Short Synthesis of 1β-Methylcarbapenem Utilizing a New Dehydration Type Ti-Dieckmann Condensation." Advanced Synthesis & Catalysis 345, no. 8 (August 2003): 967–70. http://dx.doi.org/10.1002/adsc.200303065.

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30

Chande, Madhukar S., C. Sajithkumar, Hemant S. Mondkar, Pravin A. Barve, and Sachin Diwan. "ChemInform Abstract: Novel Synthesis of 1,2,4-Triazolophanes and 1,3,4-Oxadiazolophanes: A Dieckmann Condensation Approach." ChemInform 43, no. 34 (July 26, 2012): no. http://dx.doi.org/10.1002/chin.201234040.

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31

Kozhinov, Denis V., and Victor Behar. "Extension of the Tandem Conjugate Addition−Dieckmann Condensation: The Formal Synthesis of Tetracenomycin A2." Journal of Organic Chemistry 69, no. 4 (February 2004): 1378–79. http://dx.doi.org/10.1021/jo035341k.

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32

Brückner, Reinhard, and David Bernier. "Novel Synthesis of Naturally Occurring Pulvinones: A Heck Coupling, Transesterification­, and Dieckmann Condensation Strategy." Synthesis 2007, no. 15 (July 2007): 2249–72. http://dx.doi.org/10.1055/s-2007-983803.

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33

Brückner, Reinhard, and David Bernier. "Novel Synthesis of Naturally Occurring Pulvinones: A Heck Coupling, Transesterification, and Dieckmann Condensation Strategy." Synthesis 2009, no. 09 (April 24, 2009): 1582. http://dx.doi.org/10.1055/s-0028-1088054.

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34

Nakao, Michiyasu, Munehisa Toguchi, Yuki Shimabukuro, and Shigeki Sano. "Tandem thia-Michael/Dieckmann condensation of allenyl esters for the regioselective synthesis of trisubstituted thiophenes." Tetrahedron Letters 61, no. 36 (September 2020): 152271. http://dx.doi.org/10.1016/j.tetlet.2020.152271.

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35

Rabiczko, Joanna, Zofia Urbańczyk-Lipkowska, and Marek Chmielewski. "Syntheses of pyrrolizidines and indolizidines from α,β-unsaturated sugar δ-lactones via Dieckmann condensation." Tetrahedron 58, no. 7 (February 2002): 1433–41. http://dx.doi.org/10.1016/s0040-4020(02)00005-4.

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36

Koriatopoulou, Konstantina, Nikolaos Karousis, and George Varvounis. "Novel synthesis of the pyrrolo[2,1-c][1,4]benzodiazocine ring system via a Dieckmann condensation." Tetrahedron 64, no. 42 (October 2008): 10009–13. http://dx.doi.org/10.1016/j.tet.2008.07.029.

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37

BUNCE, R. A., and C. R. HARRIS. "ChemInform Abstract: Six-Membered Cyclic β-Keto Esters by Tandem Conjugate Addition- Dieckmann Condensation Reactions." ChemInform 24, no. 19 (August 20, 2010): no. http://dx.doi.org/10.1002/chin.199319129.

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38

Schobert, Rainer, Markus Petermichl, and Christine Steinert. "A Synthetic Route to the MT1-MMP Inhibitor Ancorinoside D." Synthesis 51, no. 03 (September 26, 2018): 730–38. http://dx.doi.org/10.1055/s-0037-1610287.

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A methyl ester of ancorinoside D, a 3-acyltetramic acid metabolite of a sponge Penares sollasi, was synthesised in ten steps starting from a protected β-d-glucopyranosyl-(1→4)-d-galactopyranosyltrichloroacetimidate donor. Its attachment to the left half of the 3-acyl spacer by a Schmidt glycosylation, 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO)-mediated oxidation to the uronic acid, introduction of the Z-alkene via Wittig reaction, and functionalisation of the spacer terminus with Meldrum’s acid gave a β-keto ester that reacted with dimethyl N-methyl-d-aspartate under neutral conditions to afford a fully protected ancorinoside D as the product of an unusual domino N-acylation–Dieckmann condensation. Global deprotection left a methyl ester of ancorinoside D, which resisted all saponification attempts.
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39

Tanabe, Yoo, Ryohei Nagase, Hideki Gotoh, Mayumi Katayama, and Naoki Manta. "Regioselective Synthesis of Methyl 3-Thiothiophene-2-carboxylate Derivatives Utilizing a Dehydration-Type Ti-Dieckmann Condensation." HETEROCYCLES 72, no. 1 (2007): 697. http://dx.doi.org/10.3987/com-07-s(k)56.

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40

Honda, Takahiro, and Miwako Mori. "Novel Cyclization Reaction by Tandem Michael Addition -Dieckmann Condensation Using Stannyl Anion Generated from Bu3SnSiMe3and F−." Chemistry Letters 23, no. 6 (June 1994): 1013–16. http://dx.doi.org/10.1246/cl.1994.1013.

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41

Deville, Jay P., and Victor Behar. "Tandem Conjugate Cyanide Addition−Dieckmann Condensation in the Synthesis of the ABCD-Ring System of Lactonamycin." Organic Letters 4, no. 8 (April 2002): 1403–5. http://dx.doi.org/10.1021/ol0257373.

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42

Martinez, Aaron D., Jay P. Deville, Joel L. Stevens, and Victor Behar. "Nucleophilic Partners in the Tandem Conjugate Addition−Dieckmann Condensation Reaction: 1. Synthesis of 1,2,3-Trisubstituted Naphthalenes." Journal of Organic Chemistry 69, no. 3 (February 2004): 991–92. http://dx.doi.org/10.1021/jo035342c.

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43

Rabiczko, Joanna, Zofia Urbanczyk-Lipkowska, and Marek Chmielewski. "ChemInform Abstract: Syntheses of Pyrrolizidines and Indolizidines from α,β-Unsaturated Sugar δ-Lactones via Dieckmann Condensation." ChemInform 33, no. 29 (May 20, 2010): no. http://dx.doi.org/10.1002/chin.200229149.

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44

Zhao, Fanglong, Zhiwen Liu, Shuyuan Yang, Ning Ding, and Xue Gao. "Quinolactacin Biosynthesis Involves Non‐Ribosomal‐Peptide‐Synthetase‐Catalyzed Dieckmann Condensation to Form the Quinolone‐γ‐lactam Hybrid." Angewandte Chemie International Edition 59, no. 43 (August 20, 2020): 19108–14. http://dx.doi.org/10.1002/anie.202005770.

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45

Hanessian, Stephen, Helen Sailes, Alexander Munro, and Eric Therrien. "Synthesis of Diversely Functionalized Indolizidinones and Related Bicyclic Lactams Using Intramolecular Grubbs Olefin Metathesis and Dieckmann Condensation." Journal of Organic Chemistry 68, no. 19 (September 2003): 7219–33. http://dx.doi.org/10.1021/jo030145z.

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46

Zhao, Fanglong, Zhiwen Liu, Shuyuan Yang, Ning Ding, and Xue Gao. "Quinolactacin Biosynthesis Involves Non‐Ribosomal‐Peptide‐Synthetase‐Catalyzed Dieckmann Condensation to Form the Quinolone‐γ‐lactam Hybrid." Angewandte Chemie 132, no. 43 (August 20, 2020): 19270–76. http://dx.doi.org/10.1002/ange.202005770.

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47

Mori, Naoki, Chiaki Mase, Hidenori Watanabe, and Hirosato Takikawa. "Synthetic studies on pseudolaric acid B: Construction of the trans-fused [5–7] ring system via Dieckmann condensation." Tetrahedron Letters 59, no. 26 (June 2018): 2600–2603. http://dx.doi.org/10.1016/j.tetlet.2018.05.069.

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48

Fominova, Kateryna, Taras Diachuk, Iryna V. Sadkova, and Pavel K. Mykhailiuk. "Front Cover: Synthesis of 2,2-Disubstituted Spirocyclic Pyrrolidines by Intramolecular Dieckmann Condensation (Eur. J. Org. Chem. 22/2019)." European Journal of Organic Chemistry 2019, no. 22 (May 29, 2019): 3542. http://dx.doi.org/10.1002/ejoc.201900755.

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49

Kawabata, Takeo, and Toshihide Watanabe. "Asymmetric Dieckmann Condensation via Memory of Chirality: Synthesis of the Key Intermediate for AS-3201, an Aldose Reductase Inhibitor." HETEROCYCLES 76, no. 2 (2008): 1593. http://dx.doi.org/10.3987/com-08-s(n)126.

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50

Zee, Sheng-Hsu, and Shan-Yen Chou. "The Synthesis of (±)-α-Vetispirene Via the Dieckmann Condensation of Ethyl 4-(2,6-Dimethyl-1-Carbethoxycyclohex-2-Enyl)-Butyrate." Journal of the Chinese Chemical Society 35, no. 4 (August 1988): 301–4. http://dx.doi.org/10.1002/jccs.198800044.

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