Fiesselmann thiophene synthesis

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Fiesselmann thiophene synthesis
Named after Hans Fiesselmann
Reaction type Ring forming reaction

The Fiesselmann thiophene synthesis is a name reaction in organic chemistry that allows for the generation of 3-hydroxy-2-thiophenecarboxylic acid derivatives from α,β-acetylenic esters with thioglycolic acid and its derivatives under the presence of a base.[1][2][3][4][5][6][7][8][9][10][11][12][13][14]

References[]

  1. ^ Fiesselmann, Hans; Schipprak, Peter (1954-06-01). "Über Oxythiophencarbonsäureester, I. Mitteil.: Über die Anlagerung von Thioglykolsäureester an Fumarsäure-, Maleinsäure- und Acetylendicarbonsäureester". Chemische Berichte. 87 (6): 835–841. doi:10.1002/cber.19540870608.
  2. ^ Fiesselmann, Hans; Schipprak, Peter; Zeitler, Lorenz (1954-06-01). "Über Oxythiophen-carbonsäureester, II. Mitteil.): Synthese und Reaktionen von 3-Oxy-thiophen-carbonsäure-(2)-estern". Chemische Berichte. 87 (6): 841–848. doi:10.1002/cber.19540870609.
  3. ^ Fiesselmann, Hans; Pfeiffer, Gerhard (1954-06-01). "Über Oxythiophencarbonsäureester, III. Mitteil.): Die Einwirkung von Thioglykolsäureester auf β-Ketosäureester (Mitbearbeitet von Ferdinand Memmel)". Chemische Berichte. 87 (6): 848–856. doi:10.1002/cber.19540870610.
  4. ^ Fiesselmann, Hans; Schipprak, Peter (1956-08-01). "Über Hydroxythiophencarbonsäureester, IV. Mitteil.: Eine einfache Darstellungsweise von 3-Hydroxy-thiophen- dicarbonsäure-(2.5)-estern". Chemische Berichte. 89 (8): 1897–1902. doi:10.1002/cber.19560890814.
  5. ^ Fiesselmann, Hans; Thoma, Fritz (1956-08-01). "Über Hydroxythiophencarbonsäureester, VI. Mitteil.: Darstellung von 3-Hydroxy-thiophencarbonsäure-(2)-estern aus β-Ketosäureestern". Chemische Berichte. 89 (8): 1907–1912. doi:10.1002/cber.19560890816.
  6. ^ Gronowitz, Salo (1991-01-01). Chemistry of Heterocyclic Compounds: Thiophene and Its Derivatives, Part Four, Volume 44. Chemistry of Heterocyclic Compounds: A Series of Monographs. John Wiley & Sons, Inc. p. 88-125. doi:10.1002/9780470187265. hdl:2027/mdp.39015078685115. ISBN 9780470187265.
  7. ^ Nicolaou, Kyriacos Costa; Skokotas, Golfo; Furuya, S.; Suemune, H.; Nicolaou, D. Colette (September 1990). "Golfomycin A, a Novel Designed Molecule with DNA-Cleaving Properties and Antitumor Activity". Angewandte Chemie International Edition. 29 (9): 1064–1067. doi:10.1002/anie.199010641.
  8. ^ Mullican, Michael D.; Sorenson, Roderick J.; Connor, David T.; Thueson, David O.; Kennedy, John A.; Conroy, Mary Carol (1991-07-01). "Novel thiophene-, pyrrole-, furan-, and benzene carboxamidotetrazoles as potential antiallergy agents". Journal of Medicinal Chemistry. 34 (7): 2186–2194. doi:10.1021/jm00111a039. PMID 1712394.
  9. ^ Ram, Vishnu J.; Goel, Atul; Shukla, P. K.; Kapil, A. (1997-12-16). "Synthesis of thiophenes and thieno[3,2-c]pyran-4-ones as antileishmanial and antifungal agents". Bioorganic & Medicinal Chemistry Letters. 7 (24): 3101–3106. doi:10.1016/S0960-894X(97)10153-6.
  10. ^ Showalter, H. D. Hollis; Bridges, Alexander J.; Zhou, Hairong; Sercel, Anthony D.; McMichael, Amy; Fry, David W. (1999-12-09). "Tyrosine Kinase Inhibitors. 16. 6,5,6-Tricyclic Benzothieno[3,2-d]pyrimidines and Pyrimido[5,4-b]- and -[4,5-b]indoles as Potent Inhibitors of the Epidermal Growth Factor Receptor Tyrosine Kinase". Journal of Medicinal Chemistry. 42 (26): 5464–5474. doi:10.1021/jm9903949. PMID 10639288.
  11. ^ Shkinyova, Tatyana K.; Dalinger, Igor L.; Molotov, Sergei I.; Shevelev, Svyatoslav A. (2000-06-19). "Regioselectivity of nucleophilic substitution of the nitro group in 2,4,6-trinitrobenzamide". Tetrahedron Letters. 41 (25): 4973–4975. doi:10.1016/S0040-4039(00)00750-4.
  12. ^ Redman, Anikó M.; Johnson, Jeffrey S.; Dally, Robert; Swartz, Steve; Wild, Hanno; Paulsen, Holger; Caringal, Yolanda; Gunn, David; Renick, Joel; Osterhout, Martin; Kingery-Wood, Jill; Smith, Roger A.; Lee, Wendy; Dumas, Jacques; Wilhelm, Scott M.; Housley, Timothy J.; Bhargava, Ajay; Ranges, Gerald E.; Shrikhande, Alka; Young, Deborah; Bombara, Michael; Scott, William J. (2001-01-08). "p38 Kinase inhibitors for the treatment of arthritis and osteoporosis: thienyl, furyl, and pyrrolyl ureas". Bioorganic & Medicinal Chemistry Letters. 11 (1): 9–12. doi:10.1016/S0960-894X(00)00574-6. PMID 11140741.
  13. ^ Migianu, Evelyne; Kirsch, Gilbert (2002). "Synthesis of New Thieno[b]azepinediones from α-Methylene Ketones". Synthesis. 2002 (8): 1096–1100. doi:10.1055/s-2002-31963.
  14. ^ Li, Jie Jack (2006). Name Reactions A Collection of Detailed Reaction Mechanisms. Springer. p. 230. ISBN 978-3-540-30030-4.
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