doi: 10.1016/S0040-4020(01)89066-9, Ohwada, T., Yamagata, N., and Shudo, K. (1991). The reasons for this are summarized in our introduction and were very well-detailed in several reviews (Lalli, 2000; Smirnov et al., 2012; Tabolin et al., 2017, 2018). Interestingly, the generated aci-nitroiminium chloride species 1.9 could also be involved in the reaction with two equivalents of Grignard reagent to afford oximes 1.10 in good yields (Fujisawa et al., 1983). The reduction of nitro compounds are chemical reactions of wide interest in organic chemistry. Beckmann rearrangement of this oxime did not occur, probably, under highly acidic conditions it exists in diprotonated form. Helv. All of the secondary nitroalkanes and cyclopentanone oxime significantly increased levels of 8-hydroxyguanine in both DNA and RNA and caused the appearance of DX1, RX1, and RX2. Chem.,
Soc. oxidative conversion of a primary alcohol is also achieved. Tetrahedron Lett. (2008). Synlett, 2014, 25, 1873-1878. These unusual reactions allow to design novel processes, involving C-C bond forming steps, C-H-functionalizations, ring closures, providing highly versatile tool for organic synthesis and medicinal chemistry applications. An efficient catalytic and highly enantioselective protonation of silyl ketene
Patricia Marcé, James Lynch, A. John Blacker, Jonathan M. J. Williams. doi: 10.1246/bcsj.58.2519, Smirnov, V. O., Ioffe, S. L., Tishkov, A. (1987a,b). 2,4,6-trichloro[1,3,5]triazine in N,N-dimethylformamide. Chem. doi: 10.1021/jo00265a001, Ram, S., and Ehrenkaufer, R. E. (1986). Cinchona alkaloid-based phosphoramide catalyzed highly enantioselective Michael addition of unprotected 3-substituted oxindoles to nitroolefins. -oximes using 3Å Molecular Sieves in a Solventless System. Mathieu Candy, Thierry Durand, Jean-Marie Galano, Camille Oger. Novel Transformation of Primary Nitroalkanes and Primary Alkyl Bromides to the Corresponding Carboxylic Acids. Lett., 2019, 21, 6690-6694. Synthesis 49, 3255–3268. 11, 2461-2464. respectively, Enantioselective aza-Henry reaction for the synthesis of (S)-levamisole using efficient recyclable chiral Cu(II)–amino alcohol derived complexes. developed. A., and Ioffe, S. L. (2014). Nitroacetic esters 5.7 also react under the same conditions (Coustard, 1991; El Bahhaj et al., 2014). Lin Yao, Yu Wei, Pingan Wang, Wei He, Shengyong Zhang. A convenient synthesis of ketoximes from Grignard reagents and nitro compounds activated by N,N-dimethylchloromethyleniminium chloride. proposed concerted, five-membered Cope-type hydroamination process, and calculated 407-410. alkene, alkyne and aliphatic aldoximes can be converted to nitriles in excellent
Electrooxidative coupling of salts of nitro compounds with halide, nitrite, cyanide, and phenylsulfinate anions. 5, 84849–84855. excellent yields. good yields. N,N-dichloroamines, nitriles, and aldehydes from primary
Find more information on the Altmetric Attention Score and how the score is calculated. doi: 10.1016/S0040-4039(01)81522-7, Sardarian, A. R., and Shahsavari-Fard, Z. E-mail: [email protected]. doi: 10.1016/j.tetlet.2010.12.090, Colvin, E. W., Beck, A. K., Bastani, B., Seebach, D., Kaj, Y., and Dunitz, J. D. (1980). cleavage using inorganic ammonia salt as nitrogen source under mild conditions
Scheme 11. and the direct oxidation of benzylic and related primary amines to the
Int. A general, efficient, and metal-free method for aerobic oxidation of primary Massimo Curini, Francesco Epifano, Maria Carla Marcotullio, Ornelio Rosati, Monia Rossi. Overall, instead of a new C-N bond formed in the reaction of higher primary nitroalkane homologs, here new C-C bond was introduced (Aksenov et al., 2012). Phenylation reaction of α-acylnitromethanes to give 1,2-diketone monooximes: involvement of carbon electrophile at the position α to the nitro group. Stereoselective reactions of nitro compounds in the synthesis of natural compound analogs and active pharmaceutical ingredients. Soc. Synthesis and Ocular Effects of Imidazole Nitrolic Acids. Dichloroacetonitrile preferentially reacts with amides over
Electrospray ionization mass spectrometric studies of some imidazole amidoximes and nitrolic acids and their esters. the
Synthesis of 2-(methylthio)-3H-indol-3-one 3-oximes from 1-(arylamino)-1-(methylthio)-2-nitroethenes. Lett., 2016, 18,
The nitriles were obtained in good
Teresa E. Campano, Igor Iriarte, Olatz Olaizola, Julen Etxabe, Antonia Mielgo, Iñaki Ganboa, José M. Odriozola, Jesús M. García, Mikel Oiarbide, Claudio Palomo. It should be pointed out, that this reaction might take a different route at elevated temperatures. S. A. Shipilovskikh, V. Yu. Eugenia Marqués-López, Pedro Merino, Tomás Tejero, Raquel P. Herrera. Tetrahedron 51, 10929–10940. Sandip
Front. It should be pointed out, that formation of six-membered ring is normally accompanied by loss of oxime functionality and aromatization, leading to the formation of isoquinoline-3-ones 10.10 in poor yields (Scheme 10, Equation 2) (Fante et al., 2014a). Jing Li, Martin J. Lear, Yujiro Hayashi. 53, 878–879. efficiently converted into the corresponding nitriles in good yields by
228-231. about 400 mA more cathodic). The resulting methylcarbonocyanidate N-oxide 7.2 could undergo further dimerization into bis(carbomethoxy)furoxan or could be intercepted with dipolarophiles of electron rich aromatic compounds to afford oximes 7.3 in marginal yields. Lett.,
Bull. 2015,
Behzad Zeynizadeh, Mostafa Karimkoshteh. 1,3-Dinitrobenzene 12.5 also showed similar reactivity in the presence of strong bases affording anion 12.6, which subsequently transformed into oxime 12.7 (Scheme 12, Equation 2) (Kawakami and Suzuki, 1999). Synth. 10, 2259-2261. Enantioselective Organocatalytic Addition of Nitroalkanes to Oxindolylideneindolenines for the Construction of Chiral 3,3-Disubstituted Oxindoles.