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Journal articles on the topic 'Nitro groups reduction'

Author: Grafiati

Published: 9 March 2023

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1

Khan, Rahat H. "Tellurium mediated reduction of aromatic nitro groups." Journal of Chemical Research 2000, no. 6 (2000): 290–91. http://dx.doi.org/10.3184/030823400103167336.

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2

Riley, Darren, and Nicole Neyt. "Approaches for Performing Reductions under Continuous-Flow Conditions." Synthesis 50, no. 14 (2018): 2707–20. http://dx.doi.org/10.1055/s-0037-1610153.

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A concise overview of approaches to perform reductions of various functionalities including aldehydes, ketones, esters, imines, nitriles, nitro groups, alkenes and alkynes under continuous-flow conditions are highlighted and discussed in this short review.1 Introduction2 Reduction of Aldehydes, Ketones and Esters3 Reduction of Imines and Nitriles4 Reduction of Nitro Groups5 Reduction of Alkenes6 Partial Reduction of Alkynes7 Conclusion

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3

Khan, Rahat H. "ChemInform Abstract: Tellurium Mediated Reduction of Aromatic Nitro Groups." ChemInform 31, no. 44 (2000): no. http://dx.doi.org/10.1002/chin.200044049.

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4

G.O., Obaiah, Shivaprasad K.H., Shrikanth K. Bhat, and Mylarappa M. "Selective Reduction of Aromatic Nitro Compounds to Amines From Pd Doped TiO₂ Catalyzed Nano Catalyst." ECS Transactions 107, no. 1 (2022): 1681–87. http://dx.doi.org/10.1149/10701.1681ecst.

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An efficient chemoselective reduction of aromatic nitro compounds to corresponding amino analogs was achieved using palladium doped TiO2 (Ti0.97Pd0.03O1.97) nanoparticles. The reductions are effectively carried out in the presence of aromatic nitro compounds of various other reducible functional groups such as halo, alkoxy, carbonyl, and cyanide. The reduction of aromatic nitro compounds to aromatic amines was recognized with excellent yield (100%) by using nano porous palladium as a sustainable catalyst and as a hydrogen source. Reduced amines were well characterized using PXRD, 1H NMR, and 1

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5

Moody, Christopher J., and Michael R. Pitts. "Indium as a Reducing Agent: Reduction of Aromatic Nitro Groups." Synlett 1998, no. 9 (1998): 1028. http://dx.doi.org/10.1055/s-1998-1837.

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6

Huber, Didier, Guy Andermann, and Gérard Leclerc. "Selective reduction of aromatic / aliphatic nitro groups by sodium sulfide." Tetrahedron Letters 29, no. 6 (1988): 635–38. http://dx.doi.org/10.1016/s0040-4039(00)80169-0.

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7

Austin, Rupert P., and John H. Ridd. "Novel oxidation reduction reactions involving nitro groups and methyl groups in trifluoromethanesulfonic acid." Journal of the Chemical Society, Chemical Communications, no. 21 (1992): 1599. http://dx.doi.org/10.1039/c39920001599.

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8

Dood, Amber, Patrick Fisher, Christine Bodden, et al. "Synthesis of 5,6-Diaminoacenaphthylene by Reduction of Sterically Crowded Nitro Groups with Sodium Dithionite." SynOpen 02, no. 04 (2018): 0312–15. http://dx.doi.org/10.1055/s-0037-1610406.

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5,6-Diaminoacenaphthylene was synthesized in four steps from acenaphthene. This seemingly simple molecule provides unique synthetic challenges because it is relatively difficult to reduce the nitro groups and the molecule contains a particularly reactive double bond. It was determined that the only feasible sequence for the synthesis was to nitrate acenaphthene, then brominate, eliminate, and finally selectively reduce. Several reduction methods were attempted before finding one that would completely reduce both nitro groups while leaving the double bond intact.

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9

AUSTIN, R. P., and J. H. RIDD. "ChemInform Abstract: Novel Oxidation Reduction Reactions Involving Nitro Groups and Methyl Groups in Trifluoromethanesulfonic Acid." ChemInform 24, no. 6 (2010): no. http://dx.doi.org/10.1002/chin.199306129.

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10

Sun, Shuai, Zhengjun Quan, and Xicun Wang. "Selective reduction of nitro-compounds to primary amines by nickel-catalyzed hydrosilylative reduction." RSC Advances 5, no. 103 (2015): 84574–77. http://dx.doi.org/10.1039/c5ra17731f.

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The tolerances of many functional groups, e.g. aryl-chloride, aryl-bromide, alkene, alkynyl, ester, ether, oxhydryl, carboxylic acid, cyano group, nitrine, carbonyl, acyl, thioether and some heterocycles, were studied with unprecedentedly high chemoselectivity.

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11

Diez-Cecilia, Elena, Brendan Kelly, and Isabel Rozas. "One-step double reduction of aryl nitro and carbonyl groups using hydrazine." Tetrahedron Letters 52, no. 50 (2011): 6702–4. http://dx.doi.org/10.1016/j.tetlet.2011.09.112.

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12

Korbekandi, Hassan, Paul Mather, John Gardiner, and Gill Stephens. "Reduction of aliphatic nitro groups using an obligately anaerobic whole cell biocatalyst." Enzyme and Microbial Technology 42, no. 4 (2008): 308–14. http://dx.doi.org/10.1016/j.enzmictec.2007.10.009.

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13

Smith, William B. "Observations on the reduction of aryl nitro groups with palladium-sodium borohydride." Journal of Heterocyclic Chemistry 24, no. 3 (1987): 745–48. http://dx.doi.org/10.1002/jhet.5570240340.

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14

MOODY, C. J., and M. R. PITTS. "ChemInform Abstract: Indium as a Reducing Agent: Reduction of Aromatic Nitro Groups." ChemInform 29, no. 52 (2010): no. http://dx.doi.org/10.1002/chin.199852103.

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15

Denny, William A. "Nitroaromatic Hypoxia-Activated Prodrugs for Cancer Therapy." Pharmaceuticals 15, no. 2 (2022): 187. http://dx.doi.org/10.3390/ph15020187.

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The presence of “hypoxic” tissue (with O2 levels of <0.1 mmHg) in solid tumours, resulting in quiescent tumour cells distant from blood vessels, but capable of being reactivated by reoxygenation following conventional therapy (radiation or drugs), have long been known as a limitation to successful cancer chemotherapy. This has resulted in a sustained effort to develop nitroaromatic “hypoxia-activated prodrugs” designed to undergo enzyme-based nitro group reduction selectively in these hypoxic regions, to generate active drugs. Such nitro-based prodrugs can be classified into two major group

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16

Bock, Hans, and Ulrike Lechner-Knoblauch. "Radikalionen, 69 [1, 2] Die elektrochemische Reduktion aromatischer Nitro-Verbindungen in aprotischer Lösung / Radical Ions, 69 [1, 2] The Electrochemical Reduction of Aromatic Nitro Compounds in Aprotic Solution." Zeitschrift für Naturforschung B 40, no. 11 (1985): 1463–75. http://dx.doi.org/10.1515/znb-1985-1108.

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The reduction potentials of 40 aromatic nitro compounds Rπ(NO2)n with Rπ = benzene, naphthalene, anthracene, fluorene and carbazole and n = 1 to 4 nitro groups are determined by cyclic voltammetry in DMF under aprotic conditions. The perturbation by the strongly electron accepting substituents can be rationalized via correlation with HMO eigenvalues. Based on reversibility criteria, the electrochemical behaviour is discussed and the compounds are classified with respect to reversible or irreversible one-electron transfer as well as up to 4 (quasi)-reversible reduction steps. The CV data measur

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17

Lay, Peter A., Robert K. Norris, and Paul K. Witting. "Electrochemical Studies on the Competition Between Intramolecular Electron Transfer and Intermolecular Protonation of Nitroaryl Radical Anions in the Reductions of Apical Carboxylic Acid Substituents of 2- and 3-Nitro- 9,10-dihydro-9,10-ethanoanthracene-9-carboxylic Acids." Australian Journal of Chemistry 50, no. 10 (1997): 999. http://dx.doi.org/10.1071/c97076.

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The results obtained from variable scan rate cyclic voltammetry (c.v.) on 2-nitro- and 3-nitro-9,10- dihydro-9,10-ethanoanthracene-9-carboxylic acids [(4) and (5), respectively], combined with simulations of various c.v. responses, are consistent with reduction of a benzylic acid group being facilitated by an intramolecular electron transfer process. This intramolecular process involves a one-electron reduction of the nitroaromatic group, followed by a rapid and irreversible π*(ArNO2)•- → π*(RCO2H)•- intramolecular electron transfer to the carboxylic acid group at a benzylic bridgehead positio

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18

Blasco, Rafael, Edward Moore, Victor Wray, Dietmar Pieper, Kenneth Timmis, and Francisco Castillo. "3-Nitroadipate, a Metabolic Intermediate for Mineralization of 2,4-Dinitrophenol by a New Strain of aRhodococcus Species." Journal of Bacteriology 181, no. 1 (1999): 149–52. http://dx.doi.org/10.1128/jb.181.1.149-152.1999.

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ABSTRACT The bacterial strain RB1 has been isolated by enrichment cultivation with 2,4-dinitrophenol as the sole nitrogen, carbon, and energy source and characterized, on the basis of 16S rRNA gene sequence comparison, as a Rhodococcus species closely related toRhodococcus opacus. Rhodococcus sp. strain RB1 degrades 2,4-dinitrophenol, releasing the two nitro groups from the compound as nitrite. The release of nitro groups from 2,4-dinitrophenol occurs in two steps. First, the 2-nitro group is removed as nitrite, with the production of an aliphatic nitro compound identified by 1H nuclear magnet

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19

Weßling, Michael, and Hans J. Schäfer. "Cathodic hydrodimerization of nitroolefins." Beilstein Journal of Organic Chemistry 11 (July 14, 2015): 1163–74. http://dx.doi.org/10.3762/bjoc.11.131.

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Nitroalkenes are easily accessible in high variety by condensation of aldehydes with aliphatic nitroalkanes. They belong to the group of activated alkenes that can be hydrodimerized by cathodic reduction. There are many olefins with different electron withdrawing groups used for cathodic hydrodimerization, but not much is known about the behaviour of the nitro group. Synthetic applications of this group could profit from the easy access to nitroolefins in large variety, the C–C bond formation with the introduction of two nitro groups in a 1,4-distance and the conversions of the nitro group by

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20

Austin, Rupert P., and John H. Ridd. "Oxidation reduction reactions involving nitro groups in trifluoromethanesulfonic acid. Part 2. The reactions of chloromethylbenzenes with aromatic nitro Compounds." Journal of the Chemical Society, Perkin Transactions 2, no. 6 (1994): 1205. http://dx.doi.org/10.1039/p29940001205.

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21

Scheuerman, Randall A., and David Tumelty. "The reduction of aromatic nitro groups on solid supports using sodium hydrosulfite (Na2S2O4)." Tetrahedron Letters 41, no. 34 (2000): 6531–35. http://dx.doi.org/10.1016/s0040-4039(00)00959-x.

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22

Quinn, John F., Cole E. Bryant, Kathryn C. Golden, and Brian T. Gregg. "Rapid reduction of heteroaromatic nitro groups using catalytic transfer hydrogenation with microwave heating." Tetrahedron Letters 51, no. 5 (2010): 786–89. http://dx.doi.org/10.1016/j.tetlet.2009.12.005.

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23

Porwal, Digvijay, and Martin Oestreich. "B(C6F5)3-Catalyzed Reduction of Aromatic and Aliphatic Nitro Groups with Hydrosilanes." European Journal of Organic Chemistry 2016, no. 20 (2016): 3307–9. http://dx.doi.org/10.1002/ejoc.201600556.

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24

Xi, Juren, and Baishun Zhang. "A non-reductive electrochemical sensor for ultrasensitive detection of pM-level TNT." Analytical Methods 10, no. 38 (2018): 4639–43. http://dx.doi.org/10.1039/c8ay01522h.

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25

Lewandowska, Elzbieta, Stefan Kinastowski, and Stanislaw F. Wnuk. "Studies on the rearrangement of ortho-nitrobenzylidenemalonates and their Analogues to 2-aminobenzoate derivatives." Canadian Journal of Chemistry 80, no. 2 (2002): 192–99. http://dx.doi.org/10.1139/v02-010.

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Reaction of the diethyl 2-nitro-4-(trifluoromethyl)benzylidenemalonate with diethylamine in alcohols resulted in the reduction of the nitro group and the oxidation of the vinylic carbon attached to the phenyl ring. Simultaneous migration of the malonic fragment gave the appropriate 2-amino-4-(trifluoromethyl)benzoate esters. The presence of at least two nitro groups, or one nitro group and trifluoromethyl group on the phenyl ring, attached to the α-carbon and strongly electron withdrawing substituents at the β-carbon (CO2Et, CN) in ortho-nitrobenzylidene systems is necessary for this reductive

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26

Ma, Jiao-Xia, Xu Fang, Min Xue, and Yong Yang. "Synthesis, structure, and anion binding of functional oxacalix[4]arenes." Organic & Biomolecular Chemistry 17, no. 20 (2019): 5075–85. http://dx.doi.org/10.1039/c9ob00613c.

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Oxacalix[4]arenes obtained from the highly efficient, one-pot S<sub>N</sub>Ar reaction were post-macrocyclization functionalized through the reduction of nitro groups and hydrolysis of the ester groups to obtain several derivatives of desired solubility and anion binding property.

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27

Miller, Eric M., Cody J. Brazel, Krystina A. Brillos-Monia, et al. "Reduction Potential Predictions for Some 3-Aryl-Quinoxaline-2-Carbonitrile 1,4-Di-N-Oxide Derivatives with Known Anti-Tumor Properties." Computation 7, no. 1 (2019): 6. http://dx.doi.org/10.3390/computation7010006.

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The ability for DFT: B3LYP calculations using the 6-31g and lanl2dz basis sets to predict the electrochemical properties of twenty (20) 3-aryl-quinoxaline-2-carbonitrile 1,4-di-N-oxide derivatives with varying degrees of cytotoxic activity in dimethylformamide (DMF) was investigated. There was a strong correlation for the first reduction and moderate-to-low correlation of the second reduction of the diazine ring between the computational and the experimental data, with the exception of the derivative containing the nitro functionality. The four (4) nitro group derivatives are clear outliers in

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28

Rai, Rohit K., Arup Mahata, Sushobhan Mukhopadhyay, et al. "Room-Temperature Chemoselective Reduction of Nitro Groups Using Non-noble Metal Nanocatalysts in Water." Inorganic Chemistry 53, no. 6 (2014): 2904–9. http://dx.doi.org/10.1021/ic402674z.

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29

Vishnumurthy, K. A., and A. V. Adhikari. "Reduction of nitro compounds carrying electron withdrawing groups: A convenient approach without metal catalyst." Chemical Data Collections 20 (April 2019): 100211. http://dx.doi.org/10.1016/j.cdc.2019.100211.

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30

Diez-Cecilia, Elena, Brendan Kelly, and Isabel Rozas. "ChemInform Abstract: One-Step Double Reduction of Aryl Nitro and Carbonyl Groups Using Hydrazine." ChemInform 43, no. 14 (2012): no. http://dx.doi.org/10.1002/chin.201214064.

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31

Yang, Ruolan, Jingjing Ma, Hui Guo, et al. "Synthesis and Antitumor Activity of Evodiamine Derivatives With Nitro, Amino, and Methoxy Groups." Natural Product Communications 17, no. 2 (2022): 1934578X2110596. http://dx.doi.org/10.1177/1934578x211059645.

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MS, and IR, 1H NMR and 13C NMR spectroscopy were employed to elucidate 4 novel evodiamine (EVO) derivatives with nitro, amino, and methoxy groups, namely 2-NO2-EVO (7a), 10-OCH3-2-NO2-EVO (7b), 2-NH2-EVO (8a), and 10-OCH3-2-NH2-EVO (8b). The amino compounds (8a, 8b) were obtained by the reduction of nitro derivatives (7a, 7b) with SnCl2/HCl. The antiproliferative activities of these compounds were tested by Cell Counting Kit-8 assay for 48 h against the MDA-MB-231 and sw620 cancer cell lines, as well as the normal LO2 cells. The in vitro experiment showed that 8a possesses the most potent inhi

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32

Hammerstad, Travis A., Pooja V. Hegde, Courtney C. Aldrich, and Kathleen J. Wang. "Chemoselective Reduction of Tertiary Amides by 1,3-Diphenyldisiloxane (DPDS)." Synthesis 54, no. 09 (2021): 2205–12. http://dx.doi.org/10.1055/a-1709-3426.

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AbstractA convenient procedure for the chemoselective reduction of tertiary amides at room temperature in the presence of air and moisture using 1,3-diphenyldisiloxane (DPDS) is developed. The reaction conditions tolerate a significant number of functional groups including esters, nitriles, secondary amides, carbamates, sulfoxides, sulfones, sulfonyl fluorides, halogens, aryl-nitro groups, and arylamines. The conditions reported are the mildest to date and utilize EtOAc, a preferred solvent given its excellent safety profile and lower environmental impact. The ease of setup and broad chemosele

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33

Ullien, Daniela, Peter C. Thüne, Wolter F. Jager, Ernst J. R. Sudhölter, and Louis C. P. M. de Smet. "Controlled amino-functionalization by electrochemical reduction of bromo and nitro azobenzene layers bound to Si(111) surfaces." Phys. Chem. Chem. Phys. 16, no. 36 (2014): 19258–65. http://dx.doi.org/10.1039/c4cp02464h.

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Azo bonds and nitro groups present in electrografted layers of 4-nitrobenzenediazonium on H-terminated Si(111) can be electroreduced independently at different potentials (−1.5 V and −2.1 V vs. SCE, respectively).

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34

Theodoridou, E., A. D. Jannakoudakis, P. D. Jannakoudakis, and S. Antoniadou. "Electrochemically oxidized carbon fibres as an adsorbent for the attachment of dissolved substances. Adsorption of nitro compounds and ion-exchange of heavy metals." Canadian Journal of Chemistry 69, no. 12 (1991): 1881–85. http://dx.doi.org/10.1139/v91-272.

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The adsorption of several aromatic nitro compounds and the ion-exchange of heavy metal ions on electro-oxidized carbon fibres have been investigated using cyclic voltammetric and polarographic techniques. Electro-oxidation is performed by potentiostatic double pulse application. This procedure results in the generation of many functional —OH and —COOH groups with adsorptive and ion-exchanging properties.Multimolecular layers of adsorbed substances may be formed through a procedure of successive adsorption of the nitro-compound and electro-reduction to the corresponding amine, resulting in the

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35

Buist, Richard J., Steve C. F. Au-Yeung, and Donald R. Eaton. "The crystal field strength of the nitro ligand and the chemistry of the hexanitrocobaltate(III) anion." Canadian Journal of Chemistry 63, no. 12 (1985): 3558–67. http://dx.doi.org/10.1139/v85-584.

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The chemical and spectroscopic properties of the hexanitrocobaltate(III) anion are not in accord with the classification of the N-bonded nitrite ion as a strong field ligand. The nitro groups are rapidly displaced by other ligands, including water, and in dilute aqueous solution spontaneous reduction to Co(II) occurs. Comparison of solid state and solution vibrational and 59Co nmr spectra demonstrates that the principal species in solution is the same as in the solid. All ligands are N-bonded. However, within 2 or 3 min of dissolution new species appear. An electron transfer mechanism for liga

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36

Fobi, Kwabena, and Richard A. Bunce. "Domino Nitro Reduction-Friedländer Heterocyclization for the Preparation of Quinolines." Molecules 27, no. 13 (2022): 4123. http://dx.doi.org/10.3390/molecules27134123.

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The Friedländer synthesis offers efficient access to substituted quinolines from 2-aminobenzaldehydes and activated ketones in the presence of a base. The disadvantage of this procedure lies in the fact that relatively few 2-aminobenzaldehyde derivatives are readily available. To overcome this problem, we report a modification of this process involving the in situ reduction of 2-nitrobenzaldehydes with Fe/AcOH in the presence of active methylene compounds (AMCs) to produce substituted quinolines in high yields. The conditions are mild enough to tolerate a wide range of functionality in both re

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37

Shakhnes, A. Kh, S. S. Vorob’ev, and S. A. Shevelev. "Selective reduction of one, two, or three nitro groups in 1,3,5-trinitrobenzene with hydrazine hydrate." Russian Chemical Bulletin 55, no. 5 (2006): 938–39. http://dx.doi.org/10.1007/s11172-006-0356-2.

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38

Mathew, Joice P., and M. Srinivasan. "Silica-supported polymer-palladium complexes as catalysts for the reduction of nitro and azo groups." Polymer International 29, no. 3 (1992): 179–84. http://dx.doi.org/10.1002/pi.4990290305.

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39

Mani, R., V. Mahadevan, and M. Srinivasan. "Polymer-bound palladium acetate as a catalyst for the reduction of nitro and azo groups." Reactive Polymers 14, no. 3 (1991): 263–68. http://dx.doi.org/10.1016/0923-1137(91)90042-m.

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40

Zhandarev, V. V., V. N. Kazin, and G. S. Mironov. "ChemInform Abstract: Catalytic Liquid-Phase Reduction of Aromatic Nitro Compounds Containing Highly Reactive Functional Groups." ChemInform 32, no. 51 (2010): no. http://dx.doi.org/10.1002/chin.200151063.

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41

Johnson, Glenn R., Barth F. Smets, and Jim C. Spain. "Oxidative Transformation of Aminodinitrotoluene Isomers by Multicomponent Dioxygenases." Applied and Environmental Microbiology 67, no. 12 (2001): 5460–66. http://dx.doi.org/10.1128/aem.67.12.5460-5466.2001.

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ABSTRACT The electron-withdrawing nitro substituents of 2,4,6-trinitrotoluene (TNT) make the aromatic ring highly resistant to oxidative transformation. The typical biological transformation of TNT involves reduction of one or more of the nitro groups of the ring to produce the corresponding amine. Reduction of a single nitro substituent of TNT to an amino substituent increases the electron density of the aromatic nucleus considerably. The comparatively electron-dense nuclei of the aminodinitrotoluene (ADNT) isomers would be expected to be more susceptible to oxygenase attack than TNT. The hyp

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42

Lauwiner, Max, Ronny Roth, and Paul Rys. "Reduction of aromatic nitro compounds with hydrazine hydrate in the presence of an iron oxide/hydroxide catalyst. III. The selective reduction of nitro groups in aromatic azo compounds." Applied Catalysis A: General 177, no. 1 (1999): 9–14. http://dx.doi.org/10.1016/s0926-860x(98)00247-6.

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43

Hoang, Anh, Vera A. Kalashnikova, Olga V. Lefedova, and Dmitriy V. Filippov. "INFLUENCE OF SODIUM HYDROXIDE ADDITIVES ON HYDROGENIZATION KINETICS OF 4-NITRO-2'-HYDROXY-5'-METYLAZOBENZENE ON SKELETAL NICKEL IN AQUEOUS SOLUTION OF 2-PROPANOL." IZVESTIYA VYSSHIKH UCHEBNYKH ZAVEDENIY KHIMIYA KHIMICHESKAYA TEKHNOLOGIYA 61, no. 8 (2018): 66. http://dx.doi.org/10.6060/ivkkt201861008.5752.

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The elucidation of the sequence of transformations in compounds containing several reactive groups and the development of approaches to controlling the selectivity of the processes with their participation is of interest both from the theoretical and practical points of view. The article is devoted to the analysis of the kinetics of hydrogenation of 4-nitro-2'-hydroxy-5'-methylazobenzene in aqueous solution of 2-propanol with addition of sodium hydroxide on skeletal nickel at different initial amounts of the starting compound. An increase in the initial amount of 4-nitro-2'-hydroxy-5'-methylaz

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44

Abiraj, Keelara, Gejjalagere R. Srinivasa, and D. Channe Gowda. "Simple and Efficient Reduction of Aromatic Nitro Compounds Using Recyclable Polymer-Supported Formate and Magnesium." Australian Journal of Chemistry 58, no. 2 (2005): 149. http://dx.doi.org/10.1071/ch04220.

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Aromatic nitro compounds were chemoselectively reduced to the corresponding amines using recyclable polymer-supported formate as a hydrogen donor in the presence of low-cost magnesium powder at room temperature. Use of the immobilized hydrogen donor affords the product amine in excellent yield (90–97%) without the need for any chromatographic purification steps. This method was found to be highly facile with selectivity over several other functional groups, such as halogen, alkene, nitrile, carbonyl, ester, amide, methoxy, phenol, and hydroxyl groups.

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45

Irgashev, Roman A., Nikita A. Kazin, Gennady L. Rusinov, and Valery N. Charushin. "Nitration of 5,11-dihydroindolo[3,2-b]carbazoles and synthetic applications of their nitro-substituted derivatives." Beilstein Journal of Organic Chemistry 13 (July 14, 2017): 1396–406. http://dx.doi.org/10.3762/bjoc.13.136.

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A new general approach to double nitration of 6,12-di(hetero)aryl-substituted and 6,12-unsubstituted 5,11-dialkyl-5,11-dihydroindolo[3,2-b]carbazoles by acetyl nitrate has been developed to obtain their 2,8-dinitro and 6,12-dinitro derivatives, respectively. A formation of mono-nitro derivatives (at C-2 or C-6) from the same indolo[3,2-b]carbazoles has also been observed in several cases. Reduction of 2-nitro and 2,8-dinitro derivatives with zinc powder and hydrochloric acid has afforded 2-amino- and 2,8-diamino-substituted indolo[3,2-b]carbazoles, while reduction of 6,12-dinitro derivatives u

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46

Falkowski, Michal, Tomasz Rebis, Jaroslaw Piskorz, et al. "Multiwalled carbon nanotube/sulfanyl porphyrazine hybrids deposited on glassy carbon electrode — effect of nitro peripheral groups on electrochemical properties." Journal of Porphyrins and Phthalocyanines 21, no. 04-06 (2017): 295–301. http://dx.doi.org/10.1142/s1088424617500134.

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We report on the synthesis, MS, UV-vis, NMR, HPLC and electrochemical characterization of magnesium sulfanyl porphyrazine with 2-[2-(4-nitrophenoxy)ethoxy]ethylsulfanyl substituents in the periphery. The electrochemical properties of novel macrocycle were studied by cyclic voltammetry and differential pulse voltammetry in non-aqueous electrolyte. The experimental data indicated the occurrence of clearly defined four redox couples corresponded to one-electron reactions of the [Formula: see text]-conjugated porphyrazine ring and substituents in the periphery. Multiwalled carbon nanotube/sulfanyl

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Lee, Jung Gyu, Kyung Il Choi, Hun Yeong Koh, Youseung Kim, Yonghan Kang, and Yong Seo Cho. "Indium Mediated Reduction of Nitro and Azide Groups in the Presence of HCl in Aqueous Media." Synthesis 2001, no. 01 (2001): 0081–84. http://dx.doi.org/10.1055/s-2001-9743.

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48

Hari, Anitha, and Benjamin L. Miller. "A new method for the mild and selective reduction of aryl nitro groups on solid support." Tetrahedron Letters 40, no. 2 (1999): 245–48. http://dx.doi.org/10.1016/s0040-4039(98)02330-2.

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49

Alvarez, Marc A., Christopher L. Kitts, Pat J. Unkefer, and James L. Botsford. "Pseudomonas aeruginosastrain MA01 aerobically metabolizes the aminodinitrotoluenes produced by 2,4,6-trinitrotoluene nitro group reduction." Canadian Journal of Microbiology 41, no. 11 (1995): 984–91. http://dx.doi.org/10.1139/m95-137.

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Abstract:

Many microbes reduce the nitro substituents of 2,4,6-trinitrotoluene (TNT), producing aminodinitrotoluenes (ADNTs). These compounds are recalcitrant to further breakdown and are acutely toxic. In a search for organisms capable of metabolizing ADNTs, a bacterial strain was isolated for the ability to use 2-aminobenzoate (anthranilate) as sole C-source. This isolate, Pseudomonas aeruginosa MA01, metabolized TNT by first reducing one nitro group to form either 2-amino-4,6-dinitrotoluene (2ADNT) or 4-amino-2,6-dinitrotoluene (4ADNT). However, strain MA01 was distinct from other TNT-reducing organi

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50

Chen, Hui-Ju, Chien-Cheng Chiu, Tsui Wang, Dong-Sheng Lee, and Ta-Jung Lu. "Bis-NHC–Ag/Pd(OAc)2 Catalytic System Catalyzed Transfer Hydrogenation Reaction." Catalysts 11, no. 1 (2020): 8. http://dx.doi.org/10.3390/catal11010008.

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Abstract:

The bis-NHC–Ag/Pd(OAc)2 catalytic system (NHC = N-heterocyclic carbene), a combination of bis-NHC–Ag complex and Pd(OAc)2, was found to be a smart catalyst in the Pd-catalyzed transfer hydrogenation of various functionalized arenes and internal/terminal alkynes. The catalytic system demonstrated high efficiency for the reduction of a wide range of various functional groups such as carbonyls, alkynes, olefins, and nitro groups in good to excellent yields and high chemoselectivity for the reduction of functional groups. In addition, the protocol was successfully exploited to stereoselectivity fo

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