Uneingeschränkter Zugang

Chemistry of 2-Aryl-1-Cyano-1-Nitroethenes. Part II. Chemical Transformations


Zitieren

[1] Grimmett M.R., Comprehensive Organic Chemistry, Eds. D. Barton, W.D. Ollis, Pergamon, Oxford 1979, 4, 357–410.Search in Google Scholar

[2] Ried W., Köhler E., Königstein F.J., Reaktionen mit Nitro-acetonitril, Liebigs Annalen der Chemie, 1956, 598, 145–148.10.1002/jlac.19565980207Search in Google Scholar

[3] Amantini D., Fringuelli F., Piermatti O., Pizzo F., Vaccaro L., Water, a clean, inexpensive, and re-usable reaction medium. One-pot synthesis of (E)-2-aryl-1-cyano-1-nitroethenes, Green Chemistry, 2001, 3, 229–232.10.1039/b105522bSearch in Google Scholar

[4] Boguszewska-Czubara A., Łapczuk-Krygier A., Rykała K., Biernasiuk A., Wnorowski A., Popiołek Ł., Maziarka A., Hordyjewska A., Jasiński R., Novel synthesis scheme and in vitro antimicrobial evaluation of a panel of (E)-2-aryl-1-cyano-1-nitroethenes, Journal of Enzyme Inhibition and Medicinal Chemistry, 2015, 31, 900–907.10.3109/14756366.2015.107026426226180Search in Google Scholar

[5] Valizadeh H., Mamaghani M., Badrian A., Effect of Microwave Irradiation on Reaction of Arylaldehyde Derivatives with Some Active Methylene Compounds in Aqueous Media, Synthetic Communications, 2005, 35, 785–790.10.1081/SCC-200050942Search in Google Scholar

[6] Jasiński R., Mirosław B., Demchuk O.M., Babyuk D., Łapczuk-Krygier A., In the search for experimental and quantumchemical evidence for zwitterionic nature of (2E)-3-[4-(dimethylamino)phenyl]-2-nitroprop-2-enenitrile – An extreme example of donor–π–acceptor push–pull molecule, Journal of Molecular Structure, 2016, 1108, 689–697.10.1016/j.molstruc.2015.12.056Search in Google Scholar

[7] Nosachev S.B., Shchurova N.A., Tyrkov A.G., Reactions of 2-Benzylidenemalononitrile and 2-Nitro-3-phenyl-acrylonitrile with Aryl Azides, Russian Journal of Organic Chemistry, 2011, 47, 577–580.10.1134/S107042801104018XSearch in Google Scholar

[8] Fringuelli F., Matteucci M., Piermatti O., Pizzo F., Burla M.C., [4 + 2] Cycloadditions of Nitroalkenes in Water. Highly Asymmetric Synthesis of Functionalized Nitronates, Journal Organic Chemistry, 2001, 66, 4661–4666.10.1021/jo010182v11421789Search in Google Scholar

[9] Jasiński R., Kubik M., Łapczuk-Krygier A., Kącka A., Dresler E., Boguszewska-Czubara A., An experimental and theoretical study of the hetero Diels–Alder reactions between (E)-2-aryl-1-cyano-1-nitroethenes and ethyl vinyl ether: one-step or zwitterionic, two-step mechanism?, Reaction Kinetics, Mechanisms and Catalysis, 2014, 113, 333–345.10.1007/s11144-014-0753-8Search in Google Scholar

[10] Varma R.S., Kabalka G.W., Nitroalkenes in the Synthesis of Heterocyclic Compounds, Heterocycles, 1986, 24, 2645–2677.10.3987/R-1986-09-2645Search in Google Scholar

[11] Padwa A., Pearson W.M., Synthetic applications of 1,3-dipolar cycloaddition chemistry toward heterocycles and natural products, Wiley&Sons, 2002.10.1002/0471221902Search in Google Scholar

[12] Piet J.C., Hetet G.L., Cailleux P., Benhaoua H., Carrier R., Reactions des methylazide et phenylazide avec quelquesalcynes et olefins α-nitrees. Syntheseregiospecifique des 1,2,3 triazoles, Bulletin des Sociètès Chimiques Belges, 1996, 105, 33–44.10.1002/bscb.19961050107Search in Google Scholar

[13] AmantiniD., Fringuelli F.,PiermattiO., Pizzo F., Zunino E., Vaccaro L., Synthesis of 4-Aryl-1H-1,2,3-triazoles through TBAF-Catalyzed [3+2] Cycloaddition of 2-Aryl-1-nitroethenes with TMSN3 under Solvent-Free Conditions, The Journal of the Organic Chemistry, 2005, 70, 6526–6529.10.1021/jo050784516050724Search in Google Scholar

[14] Friguelli F., Lanari D., Pizzo F., Vaccaro L., Amberlite IRA900F as a Solid Fluoride Source for a Variety of Organic Transformations under Solvent-Free Conditions, European Journal of Organic Chemistry, 2008, 23, 3928–3932.10.1002/ejoc.200800142Search in Google Scholar

[15] Nosachev S.B., Del’netskaya K.A., Solov’ev N.A., Tyrkov A.G., Substituted 1-nitro-2-phenylethenes in reaction with N-phenacyl- and N-acetonylisoquinolinium bromides, Russian Journal of Organic Chemistry, 2010, 46, 1427–1429.10.1134/S1070428010090319Search in Google Scholar

[16] Jasiński R., Kula K., Kącka A., Mirosław B., Unexpected course of reaction between (E)-2-aryl-1-cyano-1-nitroethenes and diazafluorene: why is there no 1,3-dipolar cycloaddition?, Monatschefte für Chemie, 2017, 148, 909–915.10.1007/s00706-016-1893-5538701828458402Search in Google Scholar

[17] Jasiński R., Rzyman M., Barański A., Conjugated nitroalkenes in cycloaddition reactions. Part 2. Diels-Alder reactions of E-2-aryl-1-cyano-1-nitroethenes with cyclopentadiene, Collection of Czech Chemical Communications, 2010, 75, 919–929.10.1135/cccc2009562Search in Google Scholar

[18] Łapczuk-Krygier A., Ponikiewski Ł., Jasiński R., The crystal structure of (1RS,4RS,5RS,6SR)-5-cyano-5-nitro-6-phenyl-bicyclo[2.2.1]hept-2-ene, Crystallography Reports, 2014, 59, 961–963.10.1134/S1063774514070128Search in Google Scholar

[19] Łapczuk-Krygier A., Dresler E., Jasiński R., Ionic liquids as an effective and eco-friendly medium for synthesis of nitrosubstitutednorborenes analogs, Przemysł Chemiczny, 2016, 95, 1928–1931.Search in Google Scholar

[20] Baichurin R. I., Aboskalova N. I., Trukhin E. V., Berestovitskaya V. M., Aryl(hetaryl)-Containing gem-Cyanonitroethenes: Synthesis, Structure, and Reactions with 2,3-Dimethyl-1,3-butadiene, Russian Journal of General Chemistry, 2015, 85, 1845–1854.10.1134/S1070363215080101Search in Google Scholar

[21] Fringuelli F., Girotti R., Piermatti O., Pizzo F., Vaccaro L., Uncatalyzed and sol vent-free multicomponent process for the synthesis of biphenyl-2-carbonitrile derivatives, Organic Letters, 2006, 8, 5741–5744.10.1021/ol062253o17134261Search in Google Scholar

[22] Bellachioma G., Castrica L., Fringuelli F., Pizzo F., Vaccaro L., Catalyst- and solvent-free conditions as an environmentally benign approach to 2-aryl-3-cyano-hexahydro-4H-1,2-benzoxazine-2-oxides, Green Chemistry, 2008, 10, 327–332.10.1039/b712858dSearch in Google Scholar

[23] Kislyi V.P., Nesterov V.N., Shestopalov A.M., Semenov V.V., Heterocycles with a beta-nitroenamineframent. 1. Synthesis of 2-amino-3-nitro-pyrans from nitroacetonitrile, Russian Chemical Bulletin, 1999, 48, 1131–1134.10.1007/BF02496015Search in Google Scholar

[24] Kislyi V.P., Nesterov V.N., Shestopalov A.M., Semenov V.V., Heterocycles with a β-nitroenamine fragment. 2. Synthesis of 2-amino-3-nitropyrano[3,2-c]pyrans and 2-amino-3-nitropyrano[3,2,c]chromenes from nitroacetonitrile, Russian Chemical Bulletin, 1999, 4896, 1135–1138.Search in Google Scholar

[25] Troschütz R., Lückel A., Nitroketenaminale, 7. Mitt.: Synthese von substituierten 2-Amino-3-nitropyridinen aus 1,3-Biselektrophilen und 2-Nitroethen-1,1-diamin, Archiv der Pharmazic, 1992, 325, 785–789.10.1002/ardp.19923251208Search in Google Scholar

[26] Meichkov T.D., Demireva Z.I., Synthesis of some bis(ammonium) salts of 2,4-dinitro-3-(2-furyl)glutarodinitrile, Journal of Chemical and Engineering Data, 1984, 29, 483–484.10.1021/je00038a035Search in Google Scholar

[27] Meichkov T.D., Demireva Z.I., Tonicheva E., Synthese einigerbie-ammonium salze des 2,4-dinitro-3-(2-thienyl)glutaranitrllen, Zeitschrift für Chemie, 1985, 25, 62–63.10.1002/zfch.19850250205Search in Google Scholar

[28] Demireva Z.I., Binev I.G., Juchnovski I.N., A new, versatile acyl activating reagent for peptide synthesis: asymmetrically selective peptide synthesis by use of optically active 3-hydroxyhydantoin, Tetrahedron Letters, 1976, 18, 1523–1526.10.1016/S0040-4039(01)93092-8Search in Google Scholar

[29] Baichurin R.I., Aboskalova N.I., Turkhin E.V., Berestovitskaya V.M., Arylation of geminally activated nitroethenes, Russian Journal of Organic Chemistry, 2013, 49, 67–69.10.1134/S1070428013010120Search in Google Scholar

[30] Meichkov T.D., Demireva Z.I., Die synthese einigerbie-ammonium salze des 2,4-dinitro-3-(methoxyphenyl)glutaranitrllen, Zeitschrift für Chemie, 1985, 25, 169–170.10.1002/zfch.19850250504Search in Google Scholar

eISSN:
2353-737X
Sprache:
Englisch
Zeitrahmen der Veröffentlichung:
Volume Open
Fachgebiete der Zeitschrift:
Architektur und Design, Architektur, Architekten, Gebäude, Technik, Maschinenbau, Mechanik, Industrielle Chemie, Chemieingenieurwesen, Materialwissenschaft, andere