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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 48, 2018 - Issue 17
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Articles

Some reactions of 2-(4-substitutedphenyl)-2-(N-methyl-N-4-substitutedbenzamido) acetic acids

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Pages 2206-2220 | Received 23 Mar 2018, Published online: 09 Jul 2018

References

  • Ollis, W. D.; Ramsden, C. A. Adv. Heterocycl. Chem. 1976, 19, 1–122. DOI: 10.1016/S0065-2725(08)60230-5.
  • Ollis, W. D.; Stanforth, S. P.; Ramsden, C. A. Heterocyclic Mesomeric Betaines. Tetrahedron. 1985, 41, 2239–2329. DOI: 10.1016/S0040-4020(01)96625-6.
  • Gribble, G. W. Mesoinoic Oxazoles. In: Palmer DC Ed. The Chemistry of Heterocyclic Compounds: Oxazoles, Part A Wiley: Hoboken (N. J.), 2003; Vol. 60, pp. 473–576.
  • Gribble, G. W. Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products. In The Chemistry of Heterocyclic Compounds, (Padwa, A.; Pearson, W.H., Eds).; Wiley: New York, 2002; Vol. 59, pp. 681–753.
  • Dhawan, R.; Arndtsen, B. A. Palladium-Catalyzed Multicomponent Coupling of Alkynes, Imines, and Acid Chlorides: A Direct and Modular Approach to Pyrrole Synthesis. J. Am. Chem. Soc. 2004, 126, 468–469. DOI: 10.1021/ja039152v.
  • Lopchuk, J. M.; Gribble, G. W. The Reaction of Arynes with Münchnones: synthesis of Isoindoles and Azaisoindoles. Tetrahedron Lett. 2014, 55, 2809–2812. DOI: 10.1016/j.tetlet.2014.03.055.
  • Lopchuk, J. M.; Hughes, R. P.; Gribble, G. W. What Controls Regiochemistry in 1,3-Dipolar Cycloadditions of Münchnones with Nitrostyrenes? Org. Lett. 2013, 15, 5218–5221. DOI: 10.1021/ol402385v.
  • Marco-Martínez, J.; Reboredo, S.; Izquierdo, M.; Marcos, V.; López, J. L.; Filippone, S.; Martín, N. Enantioselective Cycloaddition of Münchnones onto [60]Fullerene: organocatalysis versus Metal Catalysis. J. Am. Chem. Soc. 2014, 136, 2897–2904. DOI: 10.1021/ja500071k.
  • Dakin, H. D.; West, R. A general reaction of amino acids. J. Biol. Chem. 1928, 78, 91–105.
  • Tran, K.-V.; Bickar, D. Dakin-West Synthesis of Beta-Aryl Ketones. J. Org. Chem. 2006, 71, 6640–6643. DOI: 10.1021/jo0607966.
  • Khodaei, M. M.; Khosropour, A. R.; Fattahpour, P. A Modified Procedure for the Dakin–West Reaction: An Efficient and Convenient Method for a One-Pot Synthesis of β-Acetamido Ketones Using Silica Sulfuric Acid as Catalyst. Tetrahedron Lett. 2005, 46, 2105–2108. DOI: 10.1016/j.tetlet.2005.01.149.
  • Luesch, H.; Yoshida, W. Y.; Moore, R. E.; Paul, V. J. Structurally Diverse New Alkaloids from Palauan Collections of the Apratoxin-Producing Marine Cyanobacterium Lyngbya Sp. J. Tetrahedron. 2002, 58, 7959–7966. DOI: 10.1016/S0040-4020(02)00895-5.
  • Krohn, K.; Franke, C.; Jones, P. G.; Aust, H.-J.; Draeger, S.; Schulz, B. Wirkstoffe Aus Pilzen, I. Isolierung, Synthese Und Biologische Wirkung Von Coniothyriomycin Sowie Synthese Und Biotestung Analoger Offenkettiger Imide. Liebigs Ann. Chem. 1992, 1992, 789–798. DOI: 10.1002/jlac.1992199201130.
  • Flatters, S. J. L.; Bennett, G. Ethosuximide Reverses Paclitaxel- and Vincristine-Induced Painful Peripheral Neuropathy. J. Pain 2004, 109, 150–161. DOI: 10.1016/j.pain.2004.01.029.
  • Maruyama, H. B.; Suhara, Y.; Suzuki-Watanabe, J.; Maeshima, Y.; Shimizu, N.; Ogura-Hamada, M.; Fujimoto, H.; Takano, K. A New Antibiotic, Fumaramidmycin I. Production, Biological Properties and Characterization of Producer Strain. J. Antibiot. 1975, 28, 636–647. DOI: 10.7164/antibiotics.28.636.
  • Stierle, A. A.; Stierle, D. B.; Patacini, B. The Berkeleyamides, Amides from the Acid Lake Fungus Penicillum Rubrum. J. Nat. Prod. 2008, 71, 856–860. DOI: 10.1021/np0705054.
  • DeMilo, A. B.; Ostromecky, D. M.; Chang, S. C.; Redfern, R. E.; Fye, R. L. Heterocyclic Analogs of Diflubenzuron as Growth and Reproduction Inhibitors of the Fall Armyworm and House Fly. J. Agric. Food Chem. 1978, 26, 164–166. DOI: 10.1021/jf60215a035.
  • DeTar, F. D. L.; Silverstein, R. Reactions of Carbodiimides. I. The Mechanisms of the Reactions of Acetic Acid with Dicyclohexylcarbodiimide 1,2. J. Am. Chem. Soc. 1966, 88, 1013–1019. DOI: 10.1021/ja00957a027.
  • Benoiton, N. L.; Chen, F. M. F. Reaction of N-t-Butoxycarbonylamino Acid Anhydrides with Tertiary Amines and Carbodi-Imides. New Precursors for 2-t-Butoxyoxazol-5(4H)-One and N-Acylureas. J. Chem. Soc, Chem. Commun. 1981, 23, 1225–1227.
  • Ślebioda, M. Substituent Effect in Reaction of Dicyclohexylcarbodiimide with Substituted Benzoic Acids. Tetrahedron. 1995, 51, 7829–7834. DOI: 10.1016/0040-4020(95)00400-3.
  • Soeta, T.; Tabatake, Y.; Fujinami, S.; Ukaji, Y. N-Heterocyclic Carbene Catalyzed Oxidative Coupling of Aldehydes with Carbodiimides under Aerobic Conditions: efficient Synthesis of N-Acylureas. Org. Lett. 2013, 15, 2088–2091. DOI: 10.1021/ol400672c.
  • Dürüst, Y.; Sağırlı, A.; Kariuki, B. M.; Knight, D. W. Tetrahedron. 2014, 70, 6012–6019. DOI: 10.1016/j.tet.2014.04.083.
  • Dürüst, Y.; Sağırlı, A. Microwave-Assisted Coupling Reaction of N-Aryl Sydnones with 2-Nitromethylenethiazolidine: unexpected Formation of (Z)-2-(Nitro((E)-p-Substitutedphenyldiazenyl)Methylene)Thiazolidines. J. Org. Chem. 2014, 79, 6380–6384. DOI: 10.1021/jo5010229.
  • Yıldırım, M.; Çelikel, D.; Dürüst, Y.; Knight, D. W.; Kariuki, B. M. A Rapid and Efficient Protocol for the Synthesis of Novel Nitrothiazolo[3,2-c]Pyrimidines via Microwave-Mediated Mannich Cyclisation. Tetrahedron. 2014, 70, 2122–2128. DOI: 10.1016/j.tet.2014.02.003.
  • Altug, C.; Burnett, A. K.; Caner, E.; Dürüst, Y.; Elliott, M. C.; Glanville, R. P. J.; Guy, C.; Westwell, A. D. An Efficient One-Pot Multicomponent Approach to 5-Amino-7-Aryl-8-Nitrothiazolo[3,2-a]Pyridines. Tetrahedron. 2011, 67, 9522–9528. DOI: 10.1016/j.tet.2011.10.005.
  • Altuğ, C.; Dürüst, Y.; Elliott, M. C. Reactions of Alkylidenepyrrolidines with α-Chlorooximes and α-Chlorohydrazones. Tetrahedron Lett. 2009, 50, 7392–7394. DOI: 10.1016/j.tetlet.2009.10.086.
  • Altuğ, C.; Dürüst, Y.; Elliott, M. C.; Kariuki, B. M. Tandem Nitrosation/Cycloaddition of Heterocyclic Enamines Using Nitrolic Acids. Tetrahedron Lett. 2009, 50, 4919–4921. DOI: 10.1016/j.tetlet.2009.06.065.
  • Dürüst, Y.; Sağırlı, E.; Sağırlı, A. Microwave-Assisted Regioselective [1,3]-Dipolar Cycloaddition of 3-Methyl-2-(Substitutedbenzylidene)-5-Oxopyrazolidin-2-Ium-1-Ides to Benzothiophene 1,1-Dioxide. Turk. J. Chem. 2015, 39, 789–800. DOI: 10.3906/kim-1502-3.
  • Bayer, H. O.; Huisgen, R.; Knorr, R.; Schaefer, F. C. Darstellung Und Eigenschaften Mesoionischer Oxazolone. Chem. Ber. 1970, 103, 2581–2597. DOI: 10.1002/cber.19701030830.
  • Kawase, M. Autoxidation of Intermediary Mesoionic 1,3-Oxazolium-5-Olates Generated from Cyclic N-Acyl.ALPHA.-Amino Acids. Chem. Pharm. Bull. 1997, 45, 1248–1253. DOI: 10.1248/cpb.45.1248.
  • Saeki, M.; Hagimoto, Y.; Uno, H.; Kawase, M. The Dakin-West Reaction of N-Acylprolines in the Presence of Inorganic Bases: Unexpected Formation of Enol Esters. Heterocycles. 2009, 79, 821–830.
  • Yu, H.; Shen, J. Peroxidation of C-H Bonds Adjacent to an Amide Nitrogen Atom under Mild Conditions. Org. Lett. 2014, 16, 3204–3207. DOI: 10.1021/ol5012168.
  • Heine, H. W.; Zibuck, R.; Vandenheuvel, W. J. A. Mechanisms for the Reactions of Nitrones with Aroyl Chlorides. J. Am. Chem. Soc. 1982, 104, 3691–3694. DOI: 10.1021/ja00377a025.
  • Rowe, J. E. The Preparation of Aryl Imidates and Diaroylamides by Phase-Transfer Catalysis. Synthesis. 1980, 1980, 114–115. DOI: 10.1055/s-1980-28934.
  • Roux, M. V.; Jiménez, P.; Martín-Luengo, M. Á.; Dávalos, J. Z.; Sun, Z.; Hosmane, R. S.; Liebman, J. F. The Elusive Antiaromaticity of Maleimides and Maleic Anhydride: Enthalpies of Formation of N-Methylmaleimide, N-Methylsuccinimide, N-Methylphthalimide, and N-Benzoyl-N-Methylbenzamide. J. Org. Chem. 1997, 62, 2732–2737. DOI: 10.1021/jo9621985.
  • Iesce, M. R.; Graziano, M. L.; Cimminiello, G.; Cermola, F.; Parrilli, M.; Scarpati, R. Route of Triacylamine Formation in the Thermal Conversion of 2,3,7-Trioxa-5-Azabicyclo[2.2.1]Hept-5-Enes Investigated by Nuclear Magnetic Resonance Experiments. J. Chem. Soc, Perkin Trans. 2 1991, 7, 1085–1089.
  • Gollnick, K.; Koegler, S. Thermal Transformations of Oxazole Endoperoxides: Rearrangements, Fragmentations and Methanol Additions. Tetrahedron Lett. 1988, 29, 1007–1010. DOI: 10.1016/0040-4039(88)85320-6.
  • Shaikh, T. M.; Hong, F. E. Efficient Method for the Oxidation of Aldehydes and Diols with Tert-Butylhydroperoxide under Transition Metal-Free Conditions. Tetrahedron. 2013, 69, 8929–8935. DOI: 10.1016/j.tet.2013.07.101.
  • Trincado, M.; Grützmacher, H.; Vizza, F.; Bianchini, C. Domino Rhodium/Palladium-Catalyzed Dehydrogenation Reactions of Alcohols to Acids by Hydrogen Transfer to Inactivated Alkenes. Chem. Eur. J. 2010, 16, 2751–2757. DOI: 10.1002/chem.200903069.

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