Synthesis of arylglyoxylic acids and their collision-induced dissociation

Synthetic Communications

Volumn 38, Issue 24, 2008, Pages 4434-4444

  Wadhwa, Kuldeep ^a   Yang, Chengxi ^a   West, Paul R ^a   Deming, Kris C ^a   Chemburkar, Sanjay R ^a   Reddy, Rajarathnam E ^a  

^a ABBOTT LABORATORIES   (United States)

Author keywords

Arylcarboxylic acids; Arylglyoxylic acids; Dissociation; Synthesis

Indexed keywords

ACETIC ACID DERIVATIVE; ARYLGLYOXYLIC ACID DERIVATIVE; CARBON MONOXIDE; CARBOXYLIC ACID DERIVATIVE; ETHYL CHLOROOXOACETIC ACID; GLYOXYLIC ACID DERIVATIVE; KETONE DERIVATIVE; OXIDE; PHENOL; SELENIUM; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CHEMICAL STRUCTURE; COLLISIONALLY ACTIVATED DISSOCIATION; MASS SPECTROMETRY; SYNTHESIS;

EID: 57349174007     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802369554     Document Type: Article

References (28)

1. Kraus, G. A.; Zhang, N. Hydrogen-atom abstraction/cyclization in synthesis: Direct synthesis of coumestan and coumestrol. J. Org. Chem. 2000, 65, 5644-5646;
2. (b) Tse, B.; Jones, A. B. A novel approach to the synthesis of 4-aryl-furan-3-ols. Tetrahedron Lett. 2001, 42, 6429-6431;
3. (c) Akiyama, T.; Suzuki, M. Lewis acid mediated [3 + 2] cycloaddition of allylgermane: Stereoselective synthesis of germyl substituted tetrahydrofurans. Chem. Commun. 1997, 2357-2358.
4. Chen, Y. T.; Seto, C. Parallel synthesis of a library of bidentate protein tyrosine phosphatase inhibitors based on the α-ketoacid motif. Bioorg. Med. Chem. Lett. 2004, 12, 3289-3298;
5. (b) Chen, Y. T.; Seto, C. Divalent and trivalent α-ketocarboxylic acids as inhibitors of protein tyrosine phosphatases. J. Med Chem. 2002, 45, 3946-3952.
6. 2O as additive. Org. Lett. 2005, 7, 5425-5427;
7. (b) Loupy, A.; Monteux, D. A. Isomannide and isosorbide as new chiral auxiliaries for the stereoselective synthesis of tertiary α-hydroxy acids. Tetrahedron 2002, 58, 1541-1549;
8. (c) Tanaka, K.; Katsurada, M.; Ohno, F.; Shiga, Y.; Oda, M. Practical asymmetric synthesis of (S)-MA20565, a wide-spectrum agricultural fungiside. J. Org. Chem. 2000, 65, 432-437.
9. For a review, see Cooper, A. J. L.; Ginos, J. Z.; Meister, A. Synthesis and properties of the α-keto acids. Chem. Rev. 1983, 83, 321-358.
10. Wesssels, M.; Konig, G. M.; Wright, A. D. New 4-methoxybenzoyl derivatives from the ascidian polycarpa aurata. J. Nat. Prod. 2001, 64, 1556-1558;
11. (b) Tsantrizos, Y. S.; Kope, H. H.; Fortin, J. A.; Ogilvie, K. K. Antifungal antibiotics from Pisolithus tinctorius. Phytochem. 1991, 30, 1113-1118.
12. Bellamy, L. J.; Williams, R. L. The infrared spectra of hydroxypyruvic acid and related compounds Biochem. J. 1958, 18, 81-84;
13. (b) Oki, M.; Hiroto, M. Intramolecular hydrogen bonding in α-keto and α-alkoxycarboxylic acids, III: Comparison of the spectra in the carbonyl region with those in the O-H stretching region. Bull. Chem. Soc. Jpn. 1961, 34, 374-377.
14. Sekiguchi, O.; Letzel, M. C.; Kuck, D.; Uggerud, E. The unimolecular dissociation of protonated glyoxylic acid: Structure and dynamics of step-by-step process. Int. J. Mass Spectrum. 2006, 255-256, 177-184.
15. Howe, R.; Rao, B. S.; Heyneker, H. 2,3-Dihydro-2-hydroxybenzo[b]furan-3- one, the cyclic hemiacetal of 2-hydroxyphenylglyoxal. J. Chem. Soc. 1967, 2510-2514;
16. (b) Nardi, D.; Massarini, E.; Rossi, S.; Degen, L.; Altucci, P.; Catalano, G.; Varone, G. L. Antiviral compounds (XVI) p-alkylthiophenylglyoxals and their derivatives. Farmaco 1974, 29, 473-481.
17. Sprenger, R. D.; Ruoff, R. M.; Frazer, A. H. Citrinin studies: Hydoxy- and methoxy-phenylglyoxylic acids. J. Am. Chem. Soc. 1950, 72, 2874-2876.
18. Matsuura, T.; Cahnmann, H. J. Model reactions for the biosynthesis of thyroxine: Structural influence of the side chain in analogs of diiodotyrosine on their conversion to analogs of thyroxine. J. Am. Chem. Soc. 1959, 81, 871-878;
19. (b) Barnish, I. T.; Cross, P. E.; Danilewicz, J. C.; Dickinson, R. C.; Stopher, D. A. Promotion of carbohydrate oxidation in the heart by some phenylglyoxylic acids. J. Med. Chem. 1981, 24, 399-404.
20. Jefford, C. W.; Boschung, A. F.; Bolsman, T. A. B. M.; Moriarty, R. M.; Melnick, B. Reaction of singlet oxygen with α-ketocarboxylic acids: Oxydative decarboxylation and peroxyacid formation. J. Am. Chem. Soc. 1976, 94, 1017-1018;
21. (b) Ando, W.; Miyazaki, H.; Akasaka, T. Decarboxylation of a-keto carboxylic acids by persulfate. Tetrahedron Lett. 1982, 23, 2655-2656.
22. Chia, C. S. B.; Taylor, M. S.; Dua, S.; Blanksby, S.; Bowie, J. H. The collision induced loss of carbon monoxide from deprotonated benzyl benzoate in the gas phase. An anionic 1,2-Wittig type rearrangement. J. Chem. Soc., Perkin Trans. 2 1998, 1435-1441;
23. (b) Viramani, M.; Mirza, U. A. Mass specta of phenoxyacetyl derivatives. Org. Mass Spectrometry 1987, 22, 406-409.
24. Nimitz, J. S.; Mosher, H. S. New synthesis of α-keto esters and acids. J. Org. Chem. 1981, 46, 211-213;
25. (b) Nakata, K.; Fujio, M.; Nishimoto, K.; Tsuno, Y. Theoretical studies on empirical structure-reactivity relationship: The Yukawa-Tsuno equation. J. Physical Org. Chem. 2003, 16, 323-335.
26. Kochergin, P. M. p-Nitrophenylglyoxylic acid. Patent SU 16219, 1964; Chem. Absract 1964, 61, 61509.
27. Pirrung, M. C.; Tepper, R. J. Photochemistry of substituted benzoylformate esters: A convenient method for the photochemical oxidation of alcohols. J. Org. Chem. 1995, 60, 2451-2465.
28. Beeb, X.; Nilius, A. M.; Merta, P. J.; Soni, N. B.; Bui, M. H.; Wagner, R. Beutel; B. A. Synthesis and SAR evaluation of oxadiazolopyrazines as selective Haemophilus influenzae antibacterial agents. Bioorg. Med. Chem. Lett. 2003, 13, 3136-3136.