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Reaction behavior of phenylacetic acid derivatives in aminomethinylation

Kreutzberger, A.; Abel, D.

Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft 302(5): 362-375

1969

ISSN/ISBN: 0376-0367
PMID: 5273061
DOI: 10.1002/ardp.19693020506
Accession: 044145030

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Summary
Im System der Phenylessigsäure (II) erfolgt unter der Einwirkung von s-Triazin (I) durch zweifache Aminomethinylierung und anschließende Cyclisierung Bildung 5-substituierter 4-Hydroxy-pyrimidine (VI). Als Sekundärreaktion des aus Phenylessigsäure-anhydrid (IX) und I primär gebildeten Aminomethinylierungsproduktes (X) tritt Bildung von 4-Hydroxy-3,5-diphenyl-pyridin (XIV) auf. Letzteres entsteht auch aus I und α,α′-Diphenyl-aceton (XV). Die aus dem Enol Xviii und I gebildete O-Aminomethinylierungsstruktur Xxii geht eine Chapman-Umlagerung unter Bildung der korrespondierenden Formaminoverbindung Xxvii ein.

References

Cavinato, G.; Toniolo, L. 1993: Influence of the reaction parameters on the Pd-HCl catalyzed synthesis of phenylacetic acid derivatives via reduction of mandelic acid derivatives with carbon monoxide Journal of Molecular Catalysis 78(1): 9-20
von Langermann, J.; Temmel, E.; Seidel-Morgenstern, A.; Lorenz, H. 2015: Solid Phase Behavior in the Chiral Systems of Various 2-Hydroxy-2-phenylacetic Acid (Mandelic Acid) Derivatives Journal of Chemical-Engineering Data 60(3): 721-728
Kreutzberger, A.; Kolter, K. 1986: Antiviral agents. 27. the aminomethinylation of 5-oxo-2-pyrazoline-3-carboxylic acid derivatives Archiv der Pharmazie 319(1): 18-25
Libman, J. 1975: Light induced charge transfer processes. Photochemical behavior of 1-cyanonaphthalene in the presence of phenylacetic acid derivatives Journal of the American Chemical Society 97(14): 4139-4141
Cavinato, G.; Toniolo, L. 1993: Palladium-catalyzed carbonylation of benzyl alcohol derivatives to phenylacetic acid derivatives Journal of Molecular Catalysis 78(2): 131-142
Isono, M. 1958: Oxidative metabolism of phenylacetic acid by Penicillium chrysogenuro Q 176 XIV An application of the biological determination of phenylacetic acid Jour Agric Chem Soc Japan: 433-435
Sohail, M.; Raza, A.R. 2012: A Novel one Pot Synthesis of o-Nitrophenylacetic Acid and Unexpected p-Nitrobenzoic Acid by HNO3-Mediated CH2 Extrusion Reaction of Phenylacetic Acid Chinese Journal of Chemistry 30(2): 353-356
Kuczynski, L.; Machon, Z.; Wykret, L. 1964: New derivatives of phenylacetic acid Dbs Pharm 16(4): 479-483
Yuri, N. Stefanovsky; Lilia, Z. Viteva 1980: Michaelreaction. IV. NaNH2catalyzed one stage reaction between phenylacetic acid dialkylamides and cinnamic acid methyl ester or dialkylamides. Influence of reaction conditions on the stereochemistry Monatshefte fur Chemie 111(6): 1287-1298
Aoki, Toshikazo; Taniguchi, Y. 1951: Studies on phenylacetic acid for penicillin fermentation. I. Estimation of phenylacetic acid in the culture broth Jour Antibiotics tokyo 4(2): 105-107
Badawi, H.M.; Förner, W. 2011: Analysis of the infrared and Raman spectra of phenylacetic acid and mandelic (2-hydroxy-2-phenylacetic) acid Spectrochimica Acta. Part a Molecular and Biomolecular Spectroscopy 78(3): 1162-1167
Toullec, J.; Mladenova, M.; Gaudemarbardone, F.; Blagoev, B. 1985: Kinetics and mechanism of the Ivanov reaction: reaction of aldehydes and ketones with phenylacetic acid magnesium enediolate Journal of Organic Chemistry 50(14): 2563-2569
Macek, J.; Smolkova Keulemansova, E. 1985: Correlation of the chromatographic retention of some phenylacetic acid and phenylpropionic acid derivatives with molecular structure Journal of Chromatography 333(2): 309-317
Schleissner, C.; Olivera, E.R.; Fernández-Valverde, M.; Luengo, J.M. 1994: Aerobic catabolism of phenylacetic acid in Pseudomonas putida U: biochemical characterization of a specific phenylacetic acid transport system and formal demonstration that phenylacetyl-coenzyme a is a catabolic intermediate Journal of Bacteriology 176(24): 7667-7676
Bayer, H.; Sauter, H.; Muller, R.; Grammenos, W.; Harreus, A.; Kirstgen, R.; Rohl, F.; Ammermann, E.; Lorenz, G. 1998: Phenylacetic acid derivatives, and use as fungicides Official Gazette of the United States Patent and Trademark Office Patents 1212(2): 1851-1852
Giannini, M.; Fedi, M. 1958: Some new iodized derivatives of 2-phenylbutyric acid and of phenylacetic acid Bollettino Chimico Farmaceutico 97(10): 602-607
Connell, R.; Goldmann, S.; Muller, U.; Lohmer, S.; Bischoff, H.; Denzer, D.; Grutzmann, R.; Wohlfeil, S. 2000: Indolyl-substituted phenylacetic acid derivatives Official Gazette of the United States Patent and Trademark Office Patents 1232(1)
Vávra, J.; Vodicka, P.; Streinz, L.ík.; Budesínský, M.; Koutek, B.ír.; Ondrácek, J.; Císarová, I. 2004: Chiral derivatives of 2-(1-naphthyl)-2-phenylacetic acid Chirality 16(9): 652-660
Santini, C.; Berger, G.D.; Han, W.; Mosley, R.; Macnaul, K.; Berger, J.; Doebber, T.; Wu, M.; Moller, D.E.; Tolman, R.L.; Sahoo, S.P. 2003: Phenylacetic acid derivatives as hPPAR agonists Bioorganic and Medicinal Chemistry Letters 13(7): 1277-1280
Geissler, H. 2003: Process for preparing phenylacetic acid derivatives Official Gazette of the United States Patent and Trademark Office Patents 1276(4)