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1

Granik, V. G., V. M. Lyubchanskaya, and T. I. Mukhanova. "The Nenitzescu reaction (review)." Pharmaceutical Chemistry Journal 27, no. 6 (1993): 413–38. http://dx.doi.org/10.1007/bf00780660.

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2

Lyubchanskaya, V. M., E. K. Panisheva, S. A. Savina, L. M. Alekseeva, A. S. Shashkov, and V. G. Granik. "Quinoneimines in the Nenitzescu reaction." Russian Chemical Bulletin 54, no. 7 (2005): 1690–99. http://dx.doi.org/10.1007/s11172-006-0024-6.

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3

Hermans, Rebecca, Max Van Hoof, Luc Van Meervelt, and Wim Dehaen. "Exploration of the Divergent Outcomes for the Nenitzescu Reaction of Piperazinone Enaminoesters." Organics 4, no. 2 (2023): 146–63. http://dx.doi.org/10.3390/org4020012.

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The Nenitzescu reaction is a condensation reaction between an enamine and a quinone, which can give rise to a wide variety of reaction products depending on the nature of the starting material and the reaction conditions. The most commonly observed products are 5-hydroxyindoles and 5-hydroxybenzofurans. Both classes are of interest since they are known to possess a variety of promising bioactivities. Despite the high chemodivergency for this reaction, it remains an interesting synthetic strategy thanks to the mild reaction conditions, easily accessible starting materials and simple reaction pr
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4

Lyubchanskaya, V. M., L. M. Alekseeva, and V. G. Granik. "Cyclic enaminoketones in the nenitzescu reaction." Pharmaceutical Chemistry Journal 31, no. 11 (1997): 612–14. http://dx.doi.org/10.1007/bf02464282.

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5

Alekseeva, L. M., T. I. Mukhanova, E. K. Panisheva, et al. "Acetyl ketene aminals in Nenitzescu reaction." Russian Chemical Bulletin 48, no. 1 (1999): 160–65. http://dx.doi.org/10.1007/bf02494420.

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6

Balaban, Alexandru T. "ChemInform Abstract: Balaban-Nenitzescu-Praill Reaction." ChemInform 43, no. 20 (2012): no. http://dx.doi.org/10.1002/chin.201220233.

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7

Lyubchanskaya, V. M., L. M. Alekseeva, and V. G. Granik. "Dienediamines: New reagents for the Nenitzescu reaction." Pharmaceutical Chemistry Journal 29, no. 9 (1995): 636–39. http://dx.doi.org/10.1007/bf02226394.

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8

Ivan, Beatrice Cristina, Mino Rodolfo Caira, and Florea Dumitrascu. "Nenitzescu Indole Synthesis: 1929-2019 Unexpected Formation of a Pyrrole-Azepine Hybrid in the Nenitzescu Indole Synthesis: A Reinvestigation." Revista de Chimie 71, no. 5 (2020): 51–57. http://dx.doi.org/10.37358/rc.20.5.8112.

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The condensation of 1,4-benzoquinones with enamines reported ninety years ago is a name reaction known as the Nenitzescu indole synthesis which has proved to be a very useful method for obtaining both 5-hydroxyindoles and nonindole derivatives. An unexpected compound containing two condensed azepine rings was isolated in 1988 from the reaction between 1,4-benzoquinone and ethyl 3-aminocinnamate performed in 1-butanol. The reinvestigation of the proposed bisazepine structure by X-ray analysis revealed instead a pyrrole-azepine hybrid having the two heterocycles rings connected by a double bond.
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9

Zhou, Bei, Zhi-Cheng Liu, Wen-Wen Qu, et al. "An environmentally benign, mild, and catalyst-free reaction of quinones with heterocyclic ketene aminals in ethanol: site-selective synthesis of rarely fused [1,2-a]indolone derivatives via an unexpected anti-Nenitzescu strategy." Green Chem. 16, no. 9 (2014): 4359–70. http://dx.doi.org/10.1039/c4gc00676c.

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10

Schenck, L. W., A. Sippel, K. Kuna, W. Frank, A. Albert, and U. Kucklaender. "Dialkyl quinone-2,3-dicarboxylates in the Nenitzescu reaction." Tetrahedron 61, no. 38 (2005): 9129–39. http://dx.doi.org/10.1016/j.tet.2005.07.032.

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11

Lyubchanskaya, Valeriya M., Svetlana A. Savina, Lyudmila M. Alekseeva, Alexander S. Shashkov, and Vladimir G. Granik. "The use of enehydrazines in the Nenitzescu reaction." Mendeleev Communications 14, no. 2 (2004): 73–74. http://dx.doi.org/10.1070/mc2004v014n02abeh001879.

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12

Alekseeva, L. M., T. I. Mukhanova, E. K. Panisheva, et al. "ChemInform Abstract: Acetyl Ketene Aminals in Nenitzescu Reaction." ChemInform 30, no. 35 (2010): no. http://dx.doi.org/10.1002/chin.199935046.

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13

LYUBCHANSKAYA, V. M., L. M. ALEKSEEVA, and V. G. GRANIK. "ChemInform Abstract: Cyclic Enaminoketones in the Nenitzescu Reaction." ChemInform 29, no. 13 (2010): no. http://dx.doi.org/10.1002/chin.199813100.

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14

Wächtler, Andreas, Matthias Bremer, David Maillard, and Thomas Mohr. "Controlling the All-trans Stereochemistry in Liquid Crystalline 4,4′-Dialkyl-[1,1′-bicyclohexyl] Compounds." Synthesis 52, no. 22 (2020): 3397–405. http://dx.doi.org/10.1055/s-0040-1707349.

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A good part of today’s liquid crystals (LCs) for display applications are derived from the Darzens–Nenitzescu reaction which, in a one-pot-process, yields 1,4-trans-acylphenylcyclohexanes from acid chlorides, benzene, and cyclohexene. A mechanism for this process is proposed based on quantum-chemical computations. The products of this reaction can be further elaborated to all-trans-4,4′-disubstituted-[1,1′-bicyclohexane] compounds, essential components in almost all fast switching LC-mixtures. An equilibration process involving carbo­cations is used to control the diastereomer distribution.
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15

Mikerova, N. I., and E. K. Panisheva. "Formation of substituted benzofuranones-2 by a Nenitzescu reaction." Chemistry of Heterocyclic Compounds 26, no. 10 (1990): 1194–95. http://dx.doi.org/10.1007/bf00472202.

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16

Lyubchanskaya, Valeriya M., Lyudmila M. Alekseeva, and Vladimir G. Granik. "The First Example of Dienediamine Utilization in the Nenitzescu Reaction." Mendeleev Communications 5, no. 2 (1995): 68–69. http://dx.doi.org/10.1070/mc1995v005n02abeh000462.

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17

Patil, Shivaputra, Renukadevi Patil, and Duane Miller. "Synthetic Applications of the Nenitzescu Reaction to Biologically Active 5-Hydroxyindoles." Current Organic Chemistry 12, no. 9 (2008): 691–717. http://dx.doi.org/10.2174/138527208784567223.

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18

Lyubchanskaya, Valeria M., Lyudmila M. Alekseeva, Svetlana A. Savina, Alexander S. Shashkov, and Vladimir G. Granik. "Novel synthesis of chromene and benzofuran derivatives via the Nenitzescu reaction." Mendeleev Communications 12, no. 1 (2002): 15–16. http://dx.doi.org/10.1070/mc2002v012n01abeh001525.

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19

Kucklaender, U., R. Bollig, W. Frank, A. Gratz, and J. Jose. "A novel application of DDQ as electrophile in the Nenitzescu reaction." Bioorganic & Medicinal Chemistry 19, no. 8 (2011): 2666–74. http://dx.doi.org/10.1016/j.bmc.2011.03.006.

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20

Tretyakova, Elena V., Lyaisan R. Yarmukhametova, Elena V. Salimova, Olga S. Kukovinets, and Lyudmila V. Parfenova. "The Nenitzescu Reaction in the Synthesis of New Abietane Diterpene Indoles." Chemistry of Heterocyclic Compounds 56, no. 10 (2020): 1366–69. http://dx.doi.org/10.1007/s10593-020-02824-z.

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21

Troschütz, Reinhard, and Jens Landwehr. "Synthesis of 3-EWG-Substituted 2-Amino-5-hydroxyindoles via Nenitzescu Reaction." Synthesis, no. 14 (2005): 2414–20. http://dx.doi.org/10.1055/s-2005-872074.

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22

LYUBCHANSKAYA, V. M., L. M. ALEKSEEVA, and V. G. GRANIK. "ChemInform Abstract: The First Example of Dienediamine Utilization in the Nenitzescu Reaction." ChemInform 26, no. 33 (2010): no. http://dx.doi.org/10.1002/chin.199533130.

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23

Willemann, Christine, Reiner Waibel, Reinhard Troschütz, Renate Grünert, and Patrick Bednarski. "Unexpected formation of pyridodiindole derivatives with cytotoxic activity via double nenitzescu reaction." Journal of Heterocyclic Chemistry 45, no. 5 (2008): 1517–19. http://dx.doi.org/10.1002/jhet.5570450546.

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24

Singh, Rashmi, Harshita Bhatia, Prabhat Prakash, Elke Debroye, Swapan Dey, and Wim Dehaen. "Tandem Nenitzescu Reaction/Nucleophilic Aromatic Substitution to Form Novel Pyrido Fused Indole Frameworks." European Journal of Organic Chemistry 2021, no. 34 (2021): 4865–75. http://dx.doi.org/10.1002/ejoc.202100827.

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25

Horsten, Tomas, Temitayo Omowumi Alegbejo Price, Luc Van Meervelt, Flavio da Silva Emery, and Wim Dehaen. "2-Imidazolidinone benzofurans as unexpected outcome of the Lewis acid mediated Nenitzescu reaction." New Journal of Chemistry 46, no. 5 (2022): 2028–32. http://dx.doi.org/10.1039/d1nj04965h.

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26

Mukhanova, Tatyana I., Elena K. Panisheva, Valeriya M. Lyubchanskaya, Lyudmila M. Alekseeva, Yuryi N. Sheinker та Vladimir G. Granik. "β-(Benzofur-2-yl)-and (indol-2-yl)enamines in the Nenitzescu reaction". Tetrahedron 53, № 1 (1997): 177–84. http://dx.doi.org/10.1016/s0040-4020(96)00961-1.

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27

Lyubchanskaya, Valeria M., Lyudmila M. Alekseeva, Svetlana A. Savina, Alexander S. Shashkov, and Vladimir G. Granik. "ChemInform Abstract: Novel Synthesis of Chromene and Benzofuran Derivatives via the Nenitzescu Reaction." ChemInform 33, no. 33 (2010): no. http://dx.doi.org/10.1002/chin.200233183.

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28

Katkevica, Daze, Peteris Trapencieris, Arne Boman, Ivars Kalvins, and Torbjörn Lundstedt. "The Nenitzescu reaction: an initial screening of experimental conditions for improvment of the yield of a model reaction." Journal of Chemometrics 18, no. 34 (2004): 183–87. http://dx.doi.org/10.1002/cem.863.

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29

Lyubchanskaya, V. M., S. A. Savina, L. M. Alekseeva, A. S. Shashkov, V. V. Chernyshev, and V. G. Granik. "The first example of the synthesis of 1-aminoindole derivatives by the Nenitzescu reaction." Russian Chemical Bulletin 53, no. 12 (2004): 2834–39. http://dx.doi.org/10.1007/s11172-005-0198-3.

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30

Lyubchanskaya, V. M., L. M. Alekseeva, and V. G. Granik. "The aza-Nenitzescu reaction. Synthesis of indazole derivatives by condensation of quinones with hydrazones." Chemistry of Heterocyclic Compounds 35, no. 5 (1999): 570–74. http://dx.doi.org/10.1007/bf02324640.

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31

Lyubchanskaya, Valeriya M., Lyudmila M. Alekseeva, and Vladimir G. Granik. "The first example of aza-Nenitzescu reaction. A new approach to the heterocyclic quinones synthesis." Tetrahedron 53, no. 44 (1997): 15005–10. http://dx.doi.org/10.1016/s0040-4020(97)01052-1.

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32

MIKEROVA, N. I., and E. K. PANISHEVA. "ChemInform Abstract: Formation of Substituted 2-Benzofuranones (II) Under the Conditions of the Nenitzescu Reaction." ChemInform 23, no. 16 (2010): no. http://dx.doi.org/10.1002/chin.199216197.

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33

MUKHANOVA, T. I., E. K. PANISHEVA, V. M. LYUBCHANSKAYA, L. M. ALEKSEEVA, YU N. SHEINKER та V. G. GRANIK. "ChemInform Abstract: β-(Benzofur-2-yl)- and (Indol-2-yl)enamines in the Nenitzescu Reaction." ChemInform 28, № 14 (2010): no. http://dx.doi.org/10.1002/chin.199714101.

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34

Du, Fangyu, Qifan Zhou, Wenjiao Sun, et al. "5-Hydroxyindole-Based EZH2 Inhibitors Assembled via TCCA-Catalyzed Condensation and Nenitzescu Reactions." Molecules 25, no. 9 (2020): 2059. http://dx.doi.org/10.3390/molecules25092059.

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5-Hydroxyindole derivatives have various demonstrated biological activities. Herein, we used 5-hydroxyindole as a synthetic starting point for structural alterations in a combinatorial process to synthesize 22 different compounds with EZH2 inhibitor pharmacophores. A series of 5-hydroxyindole-derived compounds were screened inhibitory activities against K562 cells. According to molecular modeling and in vitro biological activity assays, the preliminary structure-activity relationship was summarized. Compound L–04 improved both the H3K27Me3 reduction and antiproliferation parameters (IC50 = 52.
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35

Mukhanova, T. I., L. M. Alekseeva, A. S. Shashkov, and V. G. Granik. "Heterocyclic Quinones in the Nenitzescu Reaction. Synthesis of Furo- and Pyrrolobenzothiazoles from 2-Methyl-4,7-dioxobenzothiazole." Chemistry of Heterocyclic Compounds 41, no. 2 (2005): 221–27. http://dx.doi.org/10.1007/s10593-005-0131-6.

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36

Lyubchanskaya, V. M., L. M. Alekseeva, and V. G. Granik. "ChemInform Abstract: The aza-Nenitzescu Reaction. Synthesis of Indazole Derivatives by Condensation of Quinones with Hydrazones." ChemInform 31, no. 12 (2010): no. http://dx.doi.org/10.1002/chin.200012133.

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37

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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38

Borthakur, Moyurima, Shyamalee Gogoi, Junali Gogoi, and Romesh C. Boruah. "Lewis acid catalyzed rapid synthesis of 5-hydroxy-benzo[g]indole scaffolds by a modified Nenitzescu reaction." Tetrahedron Letters 51, no. 39 (2010): 5160–63. http://dx.doi.org/10.1016/j.tetlet.2010.07.129.

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39

Janardhanan, Jith C., Rakesh K. Mishra, Gourab Das, et al. "Functionalizable 1H -Indazoles by Palladium Catalyzed Aza-Nenitzescu Reaction: Pharmacophores to Donor-Acceptor Type Multi-Luminescent Fluorophores." Asian Journal of Organic Chemistry 7, no. 10 (2018): 2094–104. http://dx.doi.org/10.1002/ajoc.201800413.

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40

LYUBCHANSKAYA, V. M., L. M. ALEKSEEVA, and V. G. GRANIK. "ChemInform Abstract: The First Example of Aza-Nenitzescu Reaction. A New Approach to the Heterocyclic Quinones Synthesis." ChemInform 29, no. 6 (2010): no. http://dx.doi.org/10.1002/chin.199806157.

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41

Kuckländer, Uwe, Krystina Kuna, Gabriele Zerta, and Wolfgang Poll. "Untersuchung zur 6-Hydroxyindol-Bildung bei der Nenitzescu-Reaktion, IV [1]. Cyclisierung von N-(Chinonylalkyl)enaminon-Derivaten, II [2] / Investigation on the Formation of 6-Hydroxyindole in the Nenitzescu Reaction, IV [1]. Cyclization of N-(Quinonylalkyl)enaminone Derivatives, II [2]." Zeitschrift für Naturforschung B 47, no. 10 (1992): 1403–10. http://dx.doi.org/10.1515/znb-1992-1011.

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Quinonylmethylenaminones 5 and 6 are synthesized and cyclized to spiro compounds 7 and 8. Quinonylpropylenaminone 15 is made in the same way. Cyclization in acetic acid yields quinolines 11 and 12, in trifluoroacetic acid/trifluoroacetic anhydrid diacylenamine 16 is obtained. The product of 15 in perchloric acid is benzazocine 20. The structure of 20 is proven by X-ray analysis. The course of the reaction is discussed.
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42

Chun, Yu Sung, Ka Yeon Ryu, Ju Hyun Kim, Hyunik Shin та Sang-gi Lee. "Tandem Blaise–Nenitzescu reaction: one-pot synthesis of 5-hydroxy-α-(aminomethylene)benzofuran-2(3H)-ones from nitriles". Organic & Biomolecular Chemistry 9, № 5 (2011): 1317. http://dx.doi.org/10.1039/c0ob01024c.

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43

Nakanishi, Saburo, Jun-ichi Nakanishi та Toshikazu Takata. "Functionalization of η4-Dienetricarbonyiron Complexes: A Facile Route to η4-Dienetri-Carbonyliron Complexes Bearing Carbonyl GroupsVIADarzens-Nenitzescu Reaction". Synthetic Communications 28, № 11 (1998): 1967–79. http://dx.doi.org/10.1080/00397919808007171.

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44

Mukhanova, T. I., L. M. Alekseeva, A. S. Shashkov, and V. G. Granik. "Heterocyclic Quinones in ihe Nenitzescu Reaction. Synthesis of Furo- And Pyrroloquinolines from 2-Methoxycarbonyl-4-oxo-5,8-quinolinequinone." Chemistry of Heterocyclic Compounds 40, no. 1 (2004): 16–21. http://dx.doi.org/10.1023/b:cohc.0000023762.58036.6d.

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45

Troschütz, Reinhard, and Bernd Dotzauer. "Synthesis of Medicinally Interesting 2,4-Diamino-9H-pyrimido[4,5-b]indol-6-ols via Extension of the Nenitzescu Reaction." Synlett, no. 6 (2004): 1039–43. http://dx.doi.org/10.1055/s-2004-822887.

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46

Alekseeva, L. M., V. M. Lyubchanskaya, T. I. Mukhanova, E. K. Panisheva, and V. G. Granik. "Investigation by1H NMR of dienediamines as starting materials for the synthesis of indoles and benzofurans by the nenitzescu reaction." Chemistry of Heterocyclic Compounds 33, no. 3 (1997): 282–87. http://dx.doi.org/10.1007/bf02253107.

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47

Borthakur, Moyurima, Shyamalee Gogoi, Junali Gogoi, and Romesh C. Boruah. "ChemInform Abstract: Lewis Acid Catalyzed Rapid Synthesis of 5-Hydroxy-benzo[g]indole Scaffolds by a Modified Nenitzescu Reaction." ChemInform 42, no. 2 (2010): no. http://dx.doi.org/10.1002/chin.201102133.

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48

Kinugawa, Masahiko, Hitoshi Arai, Hiroshi Nishikawa, et al. "Facile synthesis of the key intermediate of EO 9 via the formation of the indole skeleton using the Nenitzescu reaction." Journal of the Chemical Society, Perkin Transactions 1, no. 21 (1995): 2677. http://dx.doi.org/10.1039/p19950002677.

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49

Chun, Yu Sung, Ka Yeon Ryu, Ju Hyun Kim, Hyunik Shin та Sang-gi Lee. "ChemInform Abstract: Tandem Blaise-Nenitzescu Reaction: One-Pot Synthesis of 5-Hydroxy-α-(aminomethylene)benzofuran-2(3H)-ones from Nitriles." ChemInform 42, № 27 (2011): no. http://dx.doi.org/10.1002/chin.201127112.

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50

Suryavanshi, Padmakar A., Vellaisamy Sridharan, and J. Carlos Menéndez. "A new CAN-catalyzed domino process related to the Nenitzescu reaction: very concise access to fused ortho-indolequinones from simple precursors." Tetrahedron 69, no. 26 (2013): 5401–6. http://dx.doi.org/10.1016/j.tet.2013.04.101.

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