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Journal articles on the topic 'Nitro-Mannich'

Author: Grafiati

Published: 4 June 2021

Last updated: 16 February 2022

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1

Noble, Adam, and James C. Anderson. "Nitro-Mannich Reaction." Chemical Reviews 113, no. 5 (2013): 2887–939. http://dx.doi.org/10.1021/cr300272t.

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2

Noble, Adam, and James C. Anderson. "ChemInform Abstract: Nitro-Mannich Reaction." ChemInform 44, no. 27 (2013): no. http://dx.doi.org/10.1002/chin.201327214.

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3

Anderson, James C., Alexander J. Blake, Paul J. Koovits, and Gregory J. Stepney. "Diastereoselective Reductive Nitro-Mannich Reactions." Journal of Organic Chemistry 77, no. 10 (2012): 4711–24. http://dx.doi.org/10.1021/jo300535h.

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4

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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5

Anderson, James C., Ian B. Campbell, Sebastien Campos, Jonathan Shannon, and Derek A. Tocher. "Stereoselective synthesis of 1,2-diamine containing indolines by a conjugate addition nitro-mannich reaction." Organic & Biomolecular Chemistry 13, no. 1 (2015): 170–77. http://dx.doi.org/10.1039/c4ob01793e.

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The sequential use of the conjugate addition nitro-Mannich reaction, nitro reduction and then Pd-catalyzed intramolecular cyclisation allows the concise, stereodivergent synthesis of complex indolines.

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6

Jakubec, Pavol, Dane M. Cockfield, Madeleine Helliwell, James Raftery, and Darren J. Dixon. "Stereoselective, nitro-Mannich/lactamisation cascades for the direct synthesis of heavily decorated 5-nitropiperidin-2-ones and related heterocycles." Beilstein Journal of Organic Chemistry 8 (April 16, 2012): 567–78. http://dx.doi.org/10.3762/bjoc.8.64.

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A versatile nitro-Mannich/lactamisation cascade for the direct stereoselective synthesis of heavily decorated 5-nitropiperidin-2-ones and related heterocycles has been developed. A highly enantioenriched substituted 5-nitropiperidin-2-one was synthesised in a four component one-pot reaction combining an enantioselective organocatalytic Michael addition with the diastereoselective nitro-Mannich/lactamisation cascade. Protodenitration and chemoselective reductive manipulation of the heterocycles was used to install contiguous and fully substituted stereocentres in the synthesis of substituted pi

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7

Dudek, Agata, and Jacek Mlynarski. "Iron-Catalyzed Asymmetric Nitro-Mannich Reaction." Journal of Organic Chemistry 82, no. 20 (2017): 11218–24. http://dx.doi.org/10.1021/acs.joc.7b01786.

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8

Gregory, Alex W., Alan Chambers, Alison Hawkins, Pavol Jakubec, and Darren J. Dixon. "Iridium-Catalyzed Reductive Nitro-Mannich Cyclization." Chemistry - A European Journal 21, no. 1 (2014): 111–14. http://dx.doi.org/10.1002/chem.201405256.

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9

Pelagalli, Alessia, Lucio Pellacani та Stefania Fioravanti. "In Pursuit of β-Amino-α-nitro-β-(trifluoromethyl) Ketones: Nitro-Mannich versus Mannich-Type Reactions". European Journal of Organic Chemistry 2017, № 23 (2017): 3373–80. http://dx.doi.org/10.1002/ejoc.201700510.

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10

Yoon, Tehshik P., and Eric N. Jacobsen. "Highly Enantioselective Thiourea-Catalyzed Nitro-Mannich Reactions." Angewandte Chemie International Edition 44, no. 3 (2005): 466–68. http://dx.doi.org/10.1002/anie.200461814.

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11

Yoon, Tehshik P., and Eric N. Jacobsen. "Highly Enantioselective Thiourea-Catalyzed Nitro-Mannich Reactions." Angewandte Chemie International Edition 44, no. 45 (2005): 7327. http://dx.doi.org/10.1002/anie.200590151.

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12

Yoon, Tehshik P., and Eric N. Jacobsen. "Highly Enantioselective Thiourea-Catalyzed Nitro-Mannich Reactions." Angewandte Chemie 117, no. 3 (2005): 470–72. http://dx.doi.org/10.1002/ange.200461814.

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13

Yoon, Tehshik P., and Eric N. Jacobsen. "Highly Enantioselective Thiourea-Catalyzed Nitro-Mannich Reactions." Angewandte Chemie 117, no. 45 (2005): 7493. http://dx.doi.org/10.1002/ange.200590150.

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14

Anderson, James C., Alexander J. Blake, Paul J. Koovits, and Gregory J. Stepney. "ChemInform Abstract: Diastereoselective Reductive Nitro-Mannich Reactions." ChemInform 43, no. 37 (2012): no. http://dx.doi.org/10.1002/chin.201237038.

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15

Matsunaga, S., M. Shibasaki, S. Handa, and V. Gnanadesikan. "syn-Selective Catalytic Asymmetric Nitro-Mannich Reactions." Synfacts 2007, no. 7 (2007): 0734. http://dx.doi.org/10.1055/s-2007-968620.

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16

Disadee, Wannaporn, and Somsak Ruchirawat. "One-pot cascade synthesis of azabicycles via the nitro-Mannich reaction and N-alkylation." Organic & Biomolecular Chemistry 16, no. 5 (2018): 707–11. http://dx.doi.org/10.1039/c7ob03104a.

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17

Anderson, James C., Ian B. Campbell, Sebastien Campos, et al. "Reductive conjugate addition nitro-Mannich route for the stereoselective synthesis of 1,2,3,4-tetrahydroquinoxalines." Organic & Biomolecular Chemistry 14, no. 35 (2016): 8270–77. http://dx.doi.org/10.1039/c6ob01530a.

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18

Su, Yue, Wei Shi, Xin Chen, Shiyu Zhao, Yonghai Hui, and Zhengfeng Xie. "An aggregation-induced emission enhancement fluorescent benzoxazine-derived macromolecule: catalyst-free synthesis and its preliminary application for the determination of aqueous picric acid." RSC Advances 6, no. 47 (2016): 41340–47. http://dx.doi.org/10.1039/c6ra06942h.

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An aggregation-induced emission enhancement macromolecular benzoxazine derivative was synthesized by a catalyst-free Mannich reaction and showed a fluorescence quenching response towards nitro compounds.

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19

Brown, RFC, and RP Mcgeary. "N-Alkylation and Electrophilic Substitution Reactions of 2-Methylpyrazolo[1,5-a]pyridin-5-ol and Related Compounds." Australian Journal of Chemistry 47, no. 6 (1994): 1009. http://dx.doi.org/10.1071/ch9941009.

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2-Methylpyrazolo[1,5-a]pyridin-5-ol (1), its acetate (2), and related compounds have been subjected to N- alkylation and electrophilic substitution reactions. Bromination , nitration, nitrosation , acylation and Mannich and related reactions show a preference for 3-substitution and 3,4-disubstitution. Nitration of (1) gives 4-substitution and 3,4-disubstitution. Reductions of nitro and nitroso compounds and some transformations of a Mannich base are described.

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20

Urvashi, Urvashi, Gaurav K. Rastogi, Sandeep K. Ginotra, Alka Agarwal, and Vibha Tandon. "An expedient approach to 1,2-dihydroisoquinoline derivatives via cobalt catalysed 6-endo dig cyclization followed by Mannich condensation of o-alkynylarylaldimines." Organic & Biomolecular Chemistry 13, no. 4 (2015): 1000–1007. http://dx.doi.org/10.1039/c4ob02036g.

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A highly effective 6-endo dig cyclisation of o-alkynyl aldimines to 1,2-dihydroisoquinolines has been described via direct and nitro Mannich condensation using inexpensive and readily available cobalt chloride as catalyst.

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21

Anderson, James C., Adam Noble, and Pascual Ribelles Torres. "An intramolecular nitro-Mannich route to functionalised tetrahydroquinolines." Tetrahedron Letters 53, no. 42 (2012): 5707–10. http://dx.doi.org/10.1016/j.tetlet.2012.08.062.

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22

Gregory, Alex W., Alan Chambers, Alison Hawkins, Pavol Jakubec, and Darren J. Dixon. "ChemInform Abstract: Iridium-Catalyzed Reductive Nitro-Mannich Cyclization." ChemInform 46, no. 22 (2015): no. http://dx.doi.org/10.1002/chin.201522030.

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23

Barlin, GB, and SJ Ireland. "Potential Antimalarials. VII. Di-Mannich Bases of 4-[(7'-Trifluoromethylquinolin-4'-yl)-Aminophenol and 4-(7'-Bromo-1',5'-naphthyridin-4'-yl)]-aminophenol via 4-Nitrophenols." Australian Journal of Chemistry 41, no. 11 (1988): 1727. http://dx.doi.org/10.1071/ch9881727.

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A series of di-Mannich bases have been prepared from 4-nitrophenol and paraformaldehyde with dimethylamine, diethylamine, dipropylamine, N- (2′-hydroxyethyl)methylamine, piperidine , 3- and 4-methylpiperidine, 3,5-dimethylpiperidine or pyrrolidine. These nitro compounds were reduced catalytically to the corresponding 4-aminophenols, which reacted with 4-chloro- 7-trifluoromethylquinoline and 7-bromo-4-chloro- 1,5-naphthyridine to give the required di-Mannich bases of 4-(7′- trifluoromethylquinolin-4′-yl)- and 4-(7′-bromo-1′,5′-naphthyridin-4′-yl)-aminophenol.

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24

Brzozowski, Martin, Jose A. Forni, G. Paul Savage та Anastasios Polyzos. "The direct α-C(sp3)–H functionalisation of N-aryl tetrahydroisoquinolines via an iron-catalysed aerobic nitro-Mannich reaction and continuous flow processing". Chemical Communications 51, № 2 (2015): 334–37. http://dx.doi.org/10.1039/c4cc07913b.

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An efficient nitro-Mannich type direct α-C(sp<sup>3</sup>)–H functionalisation of N-aryl-1,2,3,4-tetrahydroisoquinolines catalysed by simple iron salts in combination with O<sub>2</sub> as the terminal oxidant is described.

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25

Barlin, GB, and JH Yan. "Potential Antimalarials. VIII. Mono- and Di-mannich Bases of 2-(7′-Trifluoro-methylquinolin-4′-ylamino)phenol Via 2-Nitrophenols." Australian Journal of Chemistry 42, no. 12 (1989): 2191. http://dx.doi.org/10.1071/ch9892191.

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Di-Mannich bases have been prepared by the reaction of 2-nitrophenol and formaldehyde with dimethylamine, diethylamine, dipropylamine, pyrrolidine, piperidine, 2-, 3- and 4-methylpiperidine, 3,5-dimethylpiperidine and morpholine. The nitro compounds were reduced catalytically to the corresponding 2-aminophenols which with 4-chloro-7-trifluoromethylquinoline gave the di-Mannich bases of 2-(7′-trifluoromethylquinolin-4′-ylamino)phenol. Analogous compounds were synthesized from 3-and 5-methyl-2-nitrophenols, and pyrrolidine. The mono-Mannich compounds, 6-(3′-methylpiperidin-1′-ylmethyl)- and 6-(p

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26

Wang, Bin, Tong Xu, Lei Zhu, et al. "Highly enantioselective nitro-Mannich reaction of ketimines under phase-transfer catalysis." Organic Chemistry Frontiers 4, no. 7 (2017): 1266–71. http://dx.doi.org/10.1039/c7qo00124j.

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A novel bifunctional phase-transfer catalyst 1i was found to be highly efficient for the nitro-Mannich reaction of unactivated ketone-derived imines with the introduction of the protecting group 6-methyl-2-pyridylsulfonyl to the ketimines. Density functional theory (DFT) calculations are also performed to give the possible transition-state model.

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27

Anderson, James C., Eva Bouvier-Israel, Christopher D. Rundell, and Xiangyu Zhang. "Asymmetric synthesis of piperidines using the nitro-Mannich reaction☆." Tetrahedron 78 (January 2021): 131821. http://dx.doi.org/10.1016/j.tet.2020.131821.

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28

Osvath, P., and AM Sargeson. "Ring Opening and Rearrangement of a Nitro-Capped Cobalt(III) Cage Complex With an N3S3 Donor Set." Australian Journal of Chemistry 47, no. 5 (1994): 807. http://dx.doi.org/10.1071/ch9940807.

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Treatment of the N3S3 donor cage complex [Co(NO2-capten)]3+ (1-methyl-8-nitro-3,13,16-trithia-6,10,19-triazabicyclo[6.6.6]icosanecobalt(III)) with excess base leads to deprotonation of a secondary coordinated amine group, followed by loss of a methylene unit from the cap by a retro-Mannich type reaction. Subsequent intermolecular hydride transfer gives a novel oxidized and partly delocalized macrocyclic complexed carbanion (13-(4-amino-2-thiabutyl)-13-methyl-6-nitro-1,11-dithia-4,8-diazacyclotetradec-4-enato(6)cobalt(III)) that is stabilized by deprotonation, and which remains deprotonated eve

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29

Mahasneh, Ali S. "Synthesis of Some 2-Aminonitroethanes via Silica Gel-Catalyzed Nitro-Mannich Reaction." Zeitschrift für Naturforschung B 61, no. 9 (2006): 1162–65. http://dx.doi.org/10.1515/znb-2006-0918.

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Abstract A direct one pot, three-component nitro-Mannich reaction of a nonenolizable aldehyde, aniline or one of its ring-substituted derivatives and nitromethane was carried out on silica gel surface. The products of the reaction, 2-aminonitroethane, were obtained in high yields. IR, 1H NMR, 13C NMR spectra and elemental analysis confirmed the structures of the products.

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30

Tanaka, Seiji, Kazuhiro Kochi, Hiroyuki Ito та ін. "Transformation of β-Nitro Alcohols to the Corresponding Nitro Imines with Lithium Hexamethyldisilazide (LHMDS) via Sequential Retro Nitro-Aldol–Nitro-Mannich Reaction". Synthetic Communications 39, № 5 (2009): 868–74. http://dx.doi.org/10.1080/00397910802432188.

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31

Kraľovičová, Eva, Alžbeta Krutošíková, Jaroslav Kováč, and Miloslava Dandárová. "Electrophilic substitution reactions of furo[3,2-b]pyrrole derivatives." Collection of Czechoslovak Chemical Communications 51, no. 1 (1986): 106–11. http://dx.doi.org/10.1135/cccc19860106.

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Formylation of ethyl 4H-furo[3,2-b]pyrrole-5-carboxylate and its N-methyl analogue afforded the 2-formyl products Ia,b which on nitration yielded 2-nitro derivatives IIc,d. Formylation, nitration, Mannich reaction, and copulation of the starting products, having position 2 occupied by an aryl, took place at the pyrrole ring.

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32

Anderson, James C., Adam Noble, and Pascual Ribelles Torres. "ChemInform Abstract: An Intramolecular Nitro-Mannich Route to Functionalized Tetrahydroquinolines." ChemInform 44, no. 5 (2013): no. http://dx.doi.org/10.1002/chin.201305118.

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33

Kranke, Birgit, and Horst Kunz. "Stereoselective synthesis of chiral piperidine derivatives employing arabinopyranosylamine as the carbohydrate auxiliary." Canadian Journal of Chemistry 84, no. 4 (2006): 625–41. http://dx.doi.org/10.1139/v06-060.

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Stereoselective synthesis of 2-substituted dehydropiperidinones and their further transformation to variously disubstituted piperidine derivatives was achieved employing D-arabinopyranosylamine as the stereodifferentiating carbohydrate auxiliary. A domino MannichMichael reaction of 1-methoxy-3-(trimethylsiloxy)butadiene (Danishefsky's diene) with O-pivaloylated arbinosylaldimines furnished N-arabinosyl dehydropiperidinones in high diastereoselectivity. Subsequent conjugate cuprate addition gave 2,6-cis-substituted piperidinones, while enolate alkylation furnished 2,3-trans-substituted dehydro

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34

Nitabaru, Tatsuya, Naoya Kumagai, and Masakatsu Shibasaki. "Catalytic Asymmetric Nitro-Mannich Reactions with a Yb/K Heterobimetallic Catalyst." Molecules 15, no. 3 (2010): 1280–90. http://dx.doi.org/10.3390/molecules15031280.

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35

Aliev, Abil, James C. Anderson, Mérina K. Corpinot та Emily S. J. Gascoigne. "Radical cyclisation studies of β-nitroamines from the nitro-Mannich reaction". Tetrahedron 74, № 38 (2018): 5458–74. http://dx.doi.org/10.1016/j.tet.2018.06.022.

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36

Anderson, James C., Andreas S. Kalogirou, Michael J. Porter, and Graham J. Tizzard. "Synthesis of the reported structure of piperazirum using a nitro-Mannich reaction as the key stereochemical determining step." Beilstein Journal of Organic Chemistry 9 (August 23, 2013): 1737–44. http://dx.doi.org/10.3762/bjoc.9.200.

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Piperazirum, isolated from Arum palaestinum Boiss, was originally assigned as r-3,c-5-diisobutyl-c-6-isopropylpiperazin-2-one. The reported structure was synthesised diastereoselectively using a key nitro-Mannich reaction to set up the C5/C6 relative stereochemistry. The structure was unambiguously assigned by single crystal X-ray diffraction but the spectroscopic data did not match those reported for the natural product. The structure of the natural product must therefore be revised.

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37

Anderson, James C., Andreas S. Kalogirou, and Graham J. Tizzard. "Conjugate addition nitro-Mannich reaction of carbon and heteroatom nucleophiles to nitroalkenes." Tetrahedron 70, no. 49 (2014): 9337–51. http://dx.doi.org/10.1016/j.tet.2014.10.042.

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38

Qian, Changtao, Feifeng Gao, and Ruifang Chen. "Yb(OiPr)3, a highly efficient catalyst for the nitro-Mannich reaction." Tetrahedron Letters 42, no. 28 (2001): 4673–75. http://dx.doi.org/10.1016/s0040-4039(01)00786-9.

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39

Yamada, Ken-ichi, Simon J Harwood, Harald Gröger, and Masakatsu Shibasaki. "Erste katalytische asymmetrische Nitro-Mannich-Reaktion mit einem neuen Heterodimetallkomplex als Katalysator." Angewandte Chemie 111, no. 23 (1999): 3713–15. http://dx.doi.org/10.1002/(sici)1521-3757(19991203)111:23<3713::aid-ange3713>3.0.co;2-z.

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40

Anderson, James C., Gareth P. Howell, Ron M. Lawrence, and Claire S. Wilson. "An Asymmetric Nitro-Mannich Reaction Applicable to Alkyl, Aryl, and Heterocyclic Imines." Journal of Organic Chemistry 70, no. 14 (2005): 5665–70. http://dx.doi.org/10.1021/jo050762i.

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41

Bosica, Giovanna, and Ramon Zammit. "One-pot multicomponent nitro-Mannich reaction using a heterogeneous catalyst under solvent-free conditions." PeerJ 6 (June 27, 2018): e5065. http://dx.doi.org/10.7717/peerj.5065.

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An environmentally-friendly, one-pot multicomponent reaction of various aldehydes, amines and nitroalkanes for the synthesis of β-nitroamines is here described. Amberlyst A-21 supported CuI was found to be a highly efficient novel heterogeneous catalyst for the three-component nitro-Mannich reaction between aldehydes, amines and nitroalkanes. The developed protocol is performed in a solvent-free medium to produce a variety of β-nitroamines in good to excellent yields within short reaction times. The catalyst can be easily prepared and recovered. It has been tested up to eight times with only a

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42

Anderson, James C., Chia-Hao Chang, Mérina K. Corpinot, Michael Nunn, and Oliver J. Ware. "Investigation of the [1,5]-hydride shift as a route to nitro-Mannich cyclisations." Tetrahedron 75, no. 48 (2019): 130663. http://dx.doi.org/10.1016/j.tet.2019.130663.

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43

Núñez, Marta G., Alistair J. M. Farley, and Darren J. Dixon. "Bifunctional Iminophosphorane Organocatalysts for Enantioselective Synthesis: Application to the Ketimine Nitro-Mannich Reaction." Journal of the American Chemical Society 135, no. 44 (2013): 16348–51. http://dx.doi.org/10.1021/ja409121s.

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44

Anderson, James C., Joshua P. Barham, and Christopher D. Rundell. "Asymmetric Intramolecular Conjugate Addition Nitro-Mannich Route to cis-2-Aryl-3-nitrotetrahydroquinolines." Organic Letters 17, no. 16 (2015): 4090–93. http://dx.doi.org/10.1021/acs.orglett.5b02036.

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45

Liu, Hui, Zhengquan Zhou, Qian Sun, et al. "Synthesis of Polysubstituted 2-Piperidinones via a Michael Addition/Nitro-Mannich/Lactamization Cascade." ACS Combinatorial Science 14, no. 6 (2012): 366–71. http://dx.doi.org/10.1021/co300022f.

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46

Pelletier, Sophie M. C., Peter C. Ray, and Darren J. Dixon. "Nitro-Mannich/Lactamization Cascades for the Direct Stereoselective Synthesis of Pyrrolidin-2-ones." Organic Letters 11, no. 20 (2009): 4512–15. http://dx.doi.org/10.1021/ol901640v.

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47

Tsuritani, Natsuko, Ken-ichi Yamada, Naoki Yoshikawa, and Masakatsu Shibasaki. "Catalytic Asymmetric Syntheses of ICI-199441 and CP-99994 Using Nitro-Mannich Reaction." Chemistry Letters 31, no. 3 (2002): 276–77. http://dx.doi.org/10.1246/cl.2002.276.

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48

Barber, David M., Hitesh J. Sanganee, and Darren J. Dixon. "One-Pot Catalytic Enantioselective Synthesis of Tetrahydropyridines via a Nitro-Mannich/Hydroamination Cascade." Organic Letters 14, no. 20 (2012): 5290–93. http://dx.doi.org/10.1021/ol302459c.

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49

Asao, Naoki, Salprima Yudha S., Tsutomu Nogami, and Yoshinori Yamamoto. "Direct Mannich and Nitro-Mannich Reactions with Non-Activated Imines: AgOTf-Catalyzed Addition of Pronucleophiles toortho-Alkynylaryl Aldimines Leading to 1,2-Dihydroisoquinolines." Angewandte Chemie International Edition 44, no. 34 (2005): 5526–28. http://dx.doi.org/10.1002/anie.200500795.

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50

Asao, Naoki, Salprima Yudha S., Tsutomu Nogami, and Yoshinori Yamamoto. "Direct Mannich and Nitro-Mannich Reactions with Non-Activated Imines: AgOTf-Catalyzed Addition of Pronucleophiles toortho-Alkynylaryl Aldimines Leading to 1,2-Dihydroisoquinolines." Angewandte Chemie 117, no. 34 (2005): 5662–64. http://dx.doi.org/10.1002/ange.200500795.

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