Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 46, 2016 - Issue 1
990
Views
25
CrossRef citations to date
0
Altmetric
SYNTHETIC COMMUNICATIONS REVIEWS

Reactivity of dehydroacetic acid in organic synthesis

&
Pages 1-30 | Received 07 Aug 2015, Published online: 28 Dec 2015

References

  • Chalaça, M. Z.; Figueroa-Villar, J. D. A theoretical and NMR study of the tautomerism of dehydroacetic acid. J. Mol. Struct. 2000, 554, 225–231.
  • Geuther, A. Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer. Wissenschaften Zeitschrift Chem. 1866, 303–308.
  • Rassweiler, C. F.; Adams, R. The structure of dehydro-acetic acid. J. Am. Chem. Soc. 1924, 46 (12), 2758–2764.
  • Wentrup, C.; Heilmayer, W.; Kollenz, G. α-Oxoketenes: Preparation and chemistry. Synthesis 1994, 1994 (12), 1219–1248.
  • Herbert, N. Farbenfabr. Bayer. Production of dehydracetic acid. US Patent 2729652, 1954.
  • Branch, S. J. Distillers Co. Preparation of dehydroacetic acid. US Patent 2849456, 1957.
  • Schmidt, J.; Schmidt, R.; Würthner, F. Synthesis, optical properties, and LFER analysis of solvent-dependent binding constants of Hamilton-receptor-connected merocyanine chromophores. J. Org. Chem. 2008, 73 (16), 6355–6362.
  • Wang, H.; Zou, Y.; Zhao, X.; Shi, D. A novel and convenient synthesis of 4-hydroxy-6-methyl-3-(1-(phenylimino)ethyl)-2H-pyran-2-one derivatives under ultrasound irradiation. Ultrason. Sonochem. 2011, 18 (5), 1048–1051.
  • Elder, R. L. The cosmetic ingredient review: A safety evaluation program. J. Am. Acad. Dermatol. 1984, 11 (6), 1168–1174.
  • Bennassi, C. A.; Semenzato, A.; Lucchiari, M.; Bettero, A. Dehydroacetic acid sodium salt stability in cosmetic preservative mixtures. Int. J. Cosmet. Sci. 1988, 10 (1), 29–32.
  • Huang, H.-Y.; Lai, Y.-C.; Chiu, C.-W.; Yeh, J.-M. Comparing micellar electrokinetic chromatography and microemulsion electrokinetic chromatography for the analysis of preservatives in pharmaceutical and cosmetic products. J. Chromatogr. A 2003, 993, 153–164.
  • Tsuda, T.; Nakanishi, H.; Morita, T.; Takebayashi, J. Simultaneous gas chromatographic determination of carboxylic acids in soft drinks and jams. J. Assoc. Offic. Anal. Chem. 1985, 68 (5), 902–905.
  • Ishiwata, H.; Nishijima, M.; Fukasawa, Y. Estimation of preservative concentrations in foods and their daily intake based on official inspection results in Japan in fiscal year 1998. Shokuhin Eiseigaku Zasshi (J. Food Hyg. Soc. Japan), 2001, 42, 404–412.
  • U.S. Food and Drug Administration. Code of Federal Regulations, Title 21, Vol. 172: Food Additives Permitted for Direct Addition to Food for Human Consumption; US Government Printing Office: Washington, DC; 2009, p. 34.
  • Smith, J.; Hong-Shum, L. Food Additives Data Book, 2nd rev. ed.; Wiley Blackwell: New York, 2011; p. 1128.
  • Chitrapriya, N.; Mahalingam, V.; Zeller, M.; Jayabalan, R.; Swaminathan, K.; Natarajan, K. Synthesis, crystal structure, and biological activities of dehydroacetic acid complexes of Ru(II) and Ru(III) containing PPh3/AsPh3. Polyhedron 2008, 27, 939–946.
  • Vara Prasad, J. V. N.; Pavlovsky, A.; Para, K. S.; Ellsworth, E. L.; Tummino, P. J.; Nouhan, C.; Ferguson, D. Nonpeptidic HIV protease inhibitors: 3-(S-benzyl substituted)-4-hydroxy-6-(phenyl substituted)-2H-pyran-2-one with an inverse mode of binding. Bioorg. Med. Chem. Lett. 1996, 6, 1133–1138.
  • (a) Phillips, D. R.; Brownlee, R. T.; Reiss, J. A.; Scourides, P. A. Bis-daunomycin hydrazones: Interactions with DNA. Invest. New Drugs 1992, 10, 79–88; (b) Tykhanov, D. A.; Sanin, E. V.; Serikova, I. I.; Yaremenko, F. G.; Roshal, A. D. Cinnamoyl pyrones in proton-donating media: Electronic structure and spectral properties of protolytic forms. Spectrochim. Acta, Part A 2011, 83, 221–230; (c) Tykhanov, D. A.; Serikova, I. I.; Yaremenko, F. G.; Roshal, A. D. Structure and spectral properties of cinnamoyl pyrones and their vinylogs. Central Eur. J. Chem. 2010, 8, 347–355.
  • Billes, F.; Eleckova, L.; Mikosch, H.; Andruch, V. Vibrational spectroscopic study of dehydroacetic acid and its cinnamoyl pyrone derivatives. Spectrochim. Acta Part A 2015, 146, 97–112.
  • Emsley, J. The structure and hydrogen bonding of the β-diketones. Struct. Bonding 1984, 57, 147.
  • Fyfe, C. A. Solid State NMR for Chemists; CFC Press: Guelph, Canada, 1983; p. 284.
  • Gorodetsky, M.; Luz, Z.; Mazur, Y. Oxygen-17 nuclear magnetic resonance studies of the equilibria between the enol forms of β-diketones. J. Am. Chem. Soc., 1967, 89 (5), 1183–1189.
  • (a) Aumiller, J. C.; Whittle, J. A. Equilibriums between alpha,beta- and beta,gamma-unsaturated ketones in six-membered rings fused beta-gamma to five-, six-, and seven-membered rings. J. Org. Chem., 1976, 41(18), 2959–2962 (b) Arndt, F.; Hartman, W. W.; Weissberger, A. Dehydroacetic acid. Org. Synth. 1940, 20, 26.
  • Stoessl, A.; Stothers, J. B. Alternaric acid: Proof of biosynthesis via condensation of two polyketide chains: Complete assignment of the 1H and 13C magnetic resonance spectra by 2D techniques. Can. J. Chem. 1984, 62, 549–553.
  • Ayer, W. A.; Villar, J. D. F. Metabolites of Lachnellula fuscosanguinea (Rehm), part 1: The isolation, structure determination, and synthesis of lachnelluloic acid. Can. J. Chem. 1985, 63, 1161–1165.
  • Walker, G. N. Reduction of enols: New synthesis of certain methoxy-benzsuberenes via hydrogenation of dehydroacetic acids. J. Am. Chem. Soc. 1956, 78 (13), 3201–3205.
  • Lokot’, I. P.; Pashkovskii, F. S.; Lakhvich, F. A. Synthesis of 3-acyl(alkyl)-6-methylpyran-2,4-diones and their derivatives. Russ. J. Org. Chem. 1999, 35, 746–755.
  • Ciba Specialty Chemicals Holding Inc. O-Coordinated metal chelates and their use in optical recording media having high storage capacity. Patent WO2005/12228, 2005, A1.
  • Pashkovsky, F. S.; Lokot, I. P.; Lakhvich, F. A. Selective reduction of the acyl group in cyclic α-acyl-β-dicarbonyl compounds with sodium cyanoboro-hydride: Efficient synthesis of cyclic α-alkyl-β-dicarbonyl compounds. Russ. Chem. Bull. 2001, 50, 324–326.
  • Collie, J. N.; Wilsmore, N. T. M. The production of naphthalene and of isoquinoline derivatives from dehydracetic acid. J. Chem. Soc. 1896, 69, 293–304.
  • Bethell, J. R.; Maitland, P. Organic reactions in aqueous solution at room temperature, part III: The influence of pH on the self-condensation of diacetyl-acetone: Constitution of Collie’s naphthalene derivative. J. Chem. Soc. 1962, 3751–3758.
  • Beaudegnies, R.; De Mesmaeker, A.; Mallinger, A.; Baalouch, M.; Goetz, A. Design and synthesis of novel spirocyclopropyl cyclohexane-1,3-diones and -1,3,5-triones for their incorporation into potent HPPD inhibitors. Tetrahedron Lett. 2010, 51, 2741–2744.
  • Merck and Co., Inc. 2-Arylthiazole derivatives as CXCr3 receptor modulators. Patent WO2007/70433, 2007, A2.
  • Solladie, G.; Colobert, F.; Denni, D. Enantioselective synthesis of C2-symmetric hexols from β,δ-diketosulfoxides. Tetrahedron: Asymmetry 1998, 9, 3081–3094.
  • Shao, L.; Kawano, H.; Saburi, M.; Uchida, Y. Asymmetric hydrogenation of 3,5-dioxoesters catalyzed by Ru-binap complex: A short step asymmetric synthesis of 6-substituted 5,6-dihydro-2-pyrones. Tetrahedron 1993, 49, 1997–2010.
  • Adams, A. D.; Santini, C. Pyridine, pyrimidine, and pyrazine derivatives as Cxcr3 receptor modulators. Patent US2009/30012, 2009, A1.
  • Solladie, G.; Huser, N. Enantioselective synthesis of a bicyclic ketal induced by chiral sulfoxides: (–)-(1 R,3 R,5S)-endo-1,3-dimethyl-2,9-dioxabicyclo-[3,3,1]nonane. Tetrahedron: Asymmetry 1995, 6 (11), 2679–2682.
  • Adkins, H.; Cramer, H. I.; Connor, R. The rate of hydrogenation of acetoacetic ester, dehydroacetic acid, benzene, phenol, and aniline over nickel at pressures from 27 to 350 atmospheres. J. Am. Chem. Soc. 1931, 53, 1402–1405.
  • Olin Corporation. Selected 2,2,6,6-tetramethyl-4-piperidinyl derivatives and their use as light stabilizers. Patent EP173050, 1991, B1.
  • Olin Corporation. Selected 2,2,6,6-tetramethyl-4-piperidinyl derivatives and their use as light stabilizers. Patent US4548973, 1985, A1.
  • Banerjee, K. S.; Deshapande, S. S. J. Indian Chem. Soc. 1975, 52, 41–44.
  • Miyaki, Y. Yakugaku Zasshi 1956, 76, 436–437; Chem. Abstr. 1956, 13808.
  • Rupe, H.; Pedrini, F.; Collin, A. Über p-Dimethylamino-benzal-Ketone III. Zur Kenntnis der auxochromen Gruppen. Helv. Chim. Acta 1932, 15, 1321–1329.
  • Pechmann, H. V.; Neger, F. Untersuchungen über die Spaltungsproducte der α-Oxysäuren. [Sechste Abhandlung.] Ueber die Einwirkung von Essigsäureanhydrid auf Acetondicarbonsäure. Justus Liebigs Ann. Chem. 1893, 273, 186–214.
  • Feist, F. Ueber neue Synthesen mittelst Dehydracetsäure. Chem. Ber. 1892, 25, 315–335.
  • Feist, F. Notizen über Dehydracetchlorid. Chem. Ber. 1892, 25, 335–339.
  • Feist, F. Zur Constitution der Dehydracetsäure. Chem. Ber. 1892, 25, 340–346.
  • Feist, F. Ueber Dehydracetsäure. Justus Liebigs Ann. Chem. 1890, 257, 253–297.
  • Gonindard, C.; Bergonzi, C.; Denier, C.; Sergheraert, C.; Klaebe, A.; et al. Synthetic hispidin, a PKC inhibitor, is more cytotoxic toward cancer cells than normal cells in vitro. Cell Biol. Toxicol. 1997, 13 (3), 141–154.
  • Collie, J. N.; Hilditch, T. P. LXXII—An isomeric change of dehydracetic acid. J. Chem. Soc., Trans. 1907, 91, 787–789.
  • Arndt, F.; Eistert, B.; Scholz, H.; Aron, E. Zur synthese der dehydracetsäure aus acetessigester. Chem. Ber. 1936, 69, 2373–2380.
  • Toray Industries, Inc. Platinum complex, process for preparing same and antitumor agent. Patent US4912100, 1990, A1.
  • Collie, N.; Myers, W. S. The formation of orcinol and other condensation products from dehydracetic acid. J. Chem. Soc., Trans. 1893, 63, 122–128.
  • Aminuddin, M.; Iqbal, J.; Gill, J. I. Dehydroacetic acid oxime as a new ligand for spectrophotometric determination of copper. J. Chem. Soc. Pak. 1999, 21, 20–23.
  • Iguchi, S.; Hisatsune, K.; Himeno, M.; Muraoka, S. Studies on pyrone derivatives, III: On the reaction of dehydroacetic acid to amino acids. Chem. Pharm. Bull. 1959, 7, 323–327.
  • Goto, S.; Toi, T. Kinetics of reaction of dehydroacetic acid, V: Reaction with primary amines. Chem. Pharm. Bull. 1971, 19, 632–637.
  • Munde, A. S.; Jagdale, A. N.; Jadhav, S. M.; Chondhekar, T. K. Synthesis, characterization, and thermal study of some transition metal complexes of an asymmetrical tetradentate Schiff base ligand. J. Serbian Chem. Soc. 2010, 75, 349–359.
  • Kannan, S.; Sivagamasundari, M.; Ramesh, R.; Liu, Y. Ruthenium(II) carbonyl complexes of dehydroacetic acid thiosemicarbazone: Synthesis, structure, light emission, and biological activity. J. Organomet. Chem. 2008, 693, 2251–2257.
  • El-Tabl, A. S.; Kashar, T. I.; El-Bahnasawy, R. M.; Ibrahim, A. E.-M. Synthesis and characterization of novel copper(II) complexes of dehydroacetic acid thiosemicarbazone. Polish J. Chem. 1999, 73, 245–254.
  • Rajnikant, D.; Kamni; Deshmukh, M. B.; Desai, S. D.; Shinde, B. S.; Kanwal, P. Synthesis and x-ray structure analysis of benzoic acid [1-(6-methyl-2,4-dioxo-3,4-dihydro-2H-pyran-3-yl)eth-(E)-ylidene]-hydrazide with a water molecule (C15H14N2O4*H2O). J. Chem. Crystallogr. 2005, 35, 357–360.
  • Mane, P. S.; Shirodkar, S. G.; Chondhekar, T. K. Synthesis of complexes of copper(II), nickel(II), cobalt(II), manganese(II), and iron(III) with bidentate Schiff bases. J. Indian Chem. Soc. 2002, 79, 376–378.
  • Strakovs, A.; Tonkikh, N. N.; Petrova, M.; Ryzhanova, K. V.; Palitis, E. The reaction of 2-aminoethyl- and 3-aminopropyl-substituted heterocycles with 2-formyl-1,3-cyclanediones and 4-oxo-3,1-benzoxazines. Chem. Heterocycl. Comp. 2002, 38, 449–455.
  • Mane, P. S.; Shirodkar, S. G.; Arbad, B. R.; Chondhekar, T. K. Indian J. Chem., Sect. A 2001, 40, 648–651.
  • Shirodkar, S. G.; Mane, P. S.; Chondhekar, T. K. Indian J. Chem., Sect. A 2001, 40, 1114–1117.
  • Glushkov, V. A.; Shklyaev, Yu. V.; Tul’bovich, G. A.; Dautova, R. Z.; Kovina, T. I.; et al. Synthesis and study of antiinflammatory and analgesic activity of 1-hydrazino-3,3-dialkyl-3,4-dihydroisoquinoline derivatives. Pharm. Chem. J. 1998, 32, 258–261; Khim. Farmatsevtich. Zh. 1998, 32, 29–32.
  • Kubaisi, A. A.; Ismail, Z. Nickel(II) and palladium(II) chelates of dehydroacetic acid Schiff bases derived from thiosemicarbazide and hydrazinecarbodithioate. Can. J. Chem. 1994, 72, 1785–1788.
  • Iguchi, S.; Inoue, A. Studies on pyrone derivatives, X: On the reaction of dehydroacetic acid to the primary amines and ammonia. Chem. Pharm. Bull. 1963, 11, 390–395.
  • Benary, E. Zur Kenntnis der Dehydracetsäure. Chem. Ber. 1910, 43, 1070–1075.
  • Stollé, R. Ueber die Condensation von Acetessigester mit Phenyl-methyl-pyrazolon und die Einwirkungsproducte von Phenylhydrazin und Hydrazin auf Dehydracetsäure. Chem. Ber. 1905, 38, 3023–3032.
  • Maiti, B. C.; Maitra, S. K. Reaction of dehydroacetic acid with aliphatic, aromatic and heterocyclic amines. Indian J. Chem. 1998, 37 B, 710–712.
  • Strakov, A. Ya.; Tonkikh, N. N.; Petrova, M. V.; Strakova, I. A. 1- and 2-(4-hydroxycarbonylphenyl)-4-oxo-4,5,6,7-tetrahydroindazoles. Chem. Heterocycl. Comp. 1997, 33, 441–444; Khim. Geterotsiklicheskikh Soedin. 1997, 4, 516–519.
  • Strakov, A. Ya.; Krasnova, A. A.; Petrova, M. V. Reactions of 4-hydrazinoquinazoline with derivatives of 1,3-cyclanediones. Chem. Heterocycl. Comp. 1996, 32 (1), 72–74; Khim. Geterotsiklicheskikh Soedin. 1996, 1, 81–83.
  • Hesse, O. Notiz über Dehydracetsäure. J. Prakt. Chem. (Leipzig) 1908, 77, 390–392.
  • Bülow, C.; Filchner, H. Über die Einwirkung von N-Amidoverbindungen auf Brom-cumalinsäureester. Chem. Ber. 1908, 41, 3281–3285.
  • Bülow, C. Einwirkung von N-Amidoverbindungen auf Dehydracetsäure. Chem. Ber. 1908, 41, 4161–4168.
  • Wang, F.; Zhang, H.; Li, L.; Hao, H.-Q.; Wang, X.-Y.; Chen, J.-G. Synthesis and characterization of chiral nickel(II) Schiff base complexes and their CD spectra-absolute configuration correlations. Tetrahedron: Asymmetry 2006, 17, 2059–2063.
  • Cindric, M.; Novak, T. K.; Uzarevic, K. Molecular and crystal structures of N,N’-propylene- and N,N’-phenylene-diylbis [3-(1-aminoethyl)-6-methyl-2H-pyran-2,4(3H)-dione]. J. Molec. Struct. 2005, 750, 135–141.
  • Rao, P. V.; Narasaiah, A. V. Synthesis, characterization and biological studies of oxovanadium(IV), manganese(II), iron(II), cobalt(II), nickle(II) and copper(II) complexes derived from a quadridentate ligand. Indian J. Chem., Sect. A, 2003, 42 (8), 1896–1899.
  • Ciba Specialty Chemicals Holding Inc. Merocyanine derivatives. Patent WO2006/3094, 2006, A2.
  • Loewe, W.; Braun, B.; Mueller, B. Novel pyranopyridine derivatives from an enaminone. J. Heterocycl. Chem. 1994, 31, 1577–1582.
  • Fadda, A. A.; Amine, M. S.; Arief, M. M. H.; Farahat, E. Kh. Novel synthesis, antimicrobial evaluation, and reactivity of dehydroacetic acid with N, C-nucleophiles. Pharmacologia 2014, 5, 1–11. Spectral data for 2-(6-methyl-2,4-dioxo-3,4-dihydro-2H-pyran-3-yl)-4H-benzo[g]chromene-10-carbaldehyde: Yellowish powder, (93%), mp 86 °C, IR (KBr): ν/ cm−1 = 3442 (broad OH), 1732 (C˭O aldehyde), 1644 (C˭O pyrone); 1H NMR (300 MHz, DMSO-d6) δ (ppm): 2.18 (s, 3H, CH3), 3.26 (d, 2H, CH2 pyrone), 5.37 (t, 1H, CH pyrone), 5.37 (s, 1H, C5-H pyrone), 7.57–7.93 (m, 3H, Ar-H), 10.37 s, 1H, CHO); 13C NMR (75 MHz, DMSO-d6) δ (ppm): 21.8, 26.8, 88.7, 97.3, 104.3, 123.3, 127.6, 130.4, 131.2, 137.5, 155.5, 157.5, 161.4, 174.3, 182.7, 191.0. MS (EI, 70 ev): m/z (%) = 334 (M+, 25). Anal. calc. for C20H14O5 (334.33): C, 71.85; H, 4.22%. Found: C, 71.79; H, 4.0%.
  • Karamouzi, S.; Maniadaki, A.; Nasiopoulou, D. A.; Kotali, E.; Kotali, A.; Harris, P. A.; Raftery, J.; Joule, J. A. Synthesis of novel octahedral silicon compounds: Synthesis of bis[3-(1-{[aryl(hydroxy)methylene]hydrazinyl-idene}ethyl)-6-methyl-2-oxo-2H-pyran-4-olato-N,O,O′]silicon(IV). Synthesis 2013, 45, 2150–2154.
  • Kotali, A.; Dimoulaki, F.; Kotali, E.; Maniadaki, A.; Harris, P. A.; Rozycka-Sokolowska, E.; Balczewski, P.; Joule, J. A. Synthesis of novel dehydroacetic acid N-aroylhydrazone-derived boron heterocycles. Tetrahedron 2015, 30, 1–5.
  • Ciba Specialty Chemicals Holding Inc. High-performance optical storage media. Patent WO2005/90362, 2005, A1.
  • Kumar, A.; Prakash, O.; Kinger, M.; Singh, S. P. Synthesis of some new 1-aryl-4-formyl-3-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)pyrazoles using the Vilsmeier-Haack reaction: Isolation of the key intermediate 1-aryl-3-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)pyrazoles. Can. J. Chem. 2006, 84, 438–442.
  • Kumar, D.; Singh, S. P.; Martinez, A.; Fruchier, A.; Elguero, J.; Martinez-Ripoll, M.; Carrio, J. S.; Virgili, A. The structure of the compounds resulting from the reaction of arylhydrazines with dehydroacetic acid: an NMR and crystallographic study. Tetrahedron 1995, 51 (16), 4891–4906.
  • Desmukh, M. B.; Shelar, M. A. Synthesis of some new N1-substituted-6-methyl-4-phenylquinolin-2(1H)-ones. J. Indian Chem. Soc. 1998, 75, 529–531.
  • Prakash, R.; Kumar, A.; Singh, S. P.; Aggarwal, R.; Prakash, O. Dehydroacetic acid and its derivatives in organic synthesis: Synthesis of some new 2-substituted-4-(5-bromo-4-hydroxy-6-methyl-2H-pyran-2-one-3-yl)thiazoles. Indian J. Chem. 2007, 46B, 1713–1715.
  • Rassweiler, C. F.; Adams, R. The structure of dehydroacetic acid. J. Am. Chem. Soc. 1924, 46 (12), 2758–2764.
  • Haitinger, L. Ueber die Dehydracetsäure. Chem. Ber. 1885, 18, 452–453.
  • Conrad, M.; Guthzeit, M. Einwirkung von Ammoniak und primären Aminbasen auf Dimethylpyrondicarbonsäureester. Chem. Ber. 1887, 20, 154–162.
  • Collie, J. N. Dehydracetic acid. J. Chem. Soc., Trans. 1900, 77, 971–977.
  • Hall, L.; Collie, J. N. Production of some nitro- and amido-oxylutidines, part II. J. Chem. Soc., Trans. 1898, 73, 235–241.
  • Brunton, S. A.; Guicherit, O. M.; Kruse, L. I. Small organic molecules as regulators of cell proliferation and their preparation. PCT Int. Appl. 2008, WO 2008057468 A1 20080515.
  • Brunton, S. A.; Guicherit, O. M.; Kruse, L. I.; Haydar, S. N.; Springer, D. M. Small organic molecules as regulators of cell proliferation and their preparation. PCT Int. Appl. 2008, WO 2008057469 A1 20080515.
  • Brunton, S. A.; Guicherit, O. M.; Kruse, L. I. Small organic molecules as regulators of cell proliferation and their preparation. PCT Int. Appl. 2008, WO 2008057497 A2 20080515.
  • Krishnan, L.; Blum, D. M.; Dilley, A. S.; Pan, S.; Potoski, J. R.; Shah, U. S.; Sharma, A.; Strong, H. L.; Wu, Y.; Zhang, M.-Y. An improved method for the preparation of substituted N-(aminocyclohexyl) benzothiophene-2-carboxamides. PCT Int. Appl. 2007, WO 2007089669 A2 20070809.
  • Taisho Pharmaceutical Co., Ltd.; Arena Pharmaceuticals, Inc. Pyridine derivatives and their use as medicaments for treating diseases related to mch receptor. Patent WO2006/35967, 2006, A1.
  • Takalo, H.; Pasanen, P.; Kankare, J. Synthesis of 4-(phenylethynyl)-2,6-bis-[N,N-bis(carboxymethyl)aminomethyl]pyridine. Acta Chem. Scandin. 1988, 42B, 373–377.
  • It is noteworthy that aniline was too unreactive to undergo condensation with pyrrylium salts according to standard procedures: A. R. Katritzky, O. Rubio, M. Szajda, B. Nowak-Wydra J. Chem. Res. Synop. 1984, 234–235.
  • Schmidt, J.; Schmidt, R.; Wuerthner, F. Synthesis, optical properties, and LFER analysis of solvent-dependent binding constants of Hamilton-receptor-connected merocyanine chromophores. J. Org. Chem. 2008, 73, 6355–6362.
  • Wurthner, F.; Schmidt, J.; Stolte, M.; Wortmann, R. Hydrogen-bond-directed head-to-tail orientation of dipolar merocyanine dyes: A strategy for the design of electrooptical materials. Angew. Chem. Int. Ed. 2006, 45, 3842–3846.
  • Hunig, von S.; Kobrich, G. Azofarbstoffe durch oxidative Kupplung V: Synthese von 1-substituierten pyridon-(4)-hydrazonen. Justus Liebigs Ann. Chem. 1958, 617, 181–202.
  • Omura, K.; Swern, D. Oxidation of alcohols by “activated” dimethyl sulfoxide: A preparative, steric and mechanistic study. Tetrahedron 1978, 34, 1651–1660.
  • Diwischek, F.; Arnone, M.; Engels, B.; Holzgrabe, U. Studies on the stereochemistry of 1,2,6-trimethyl-4-piperidone. Tetrahedron 2005, 61, 6993–7001.
  • Stanford University, Fluorophore compounds and their use in biological systems. Patent US2007/134737, 2007, A1.
  • Mane, V. G.; Patange, V. N.; Arbad, B. R. Synthesis, structural, and thermal characterization and antifungal study of manganese(II), iron(III), cobalt(II), and copper(II) complexes of N,O donor ligands. J. Indian Chem. Soc. 2007, 84, 1086–1091.
  • Ihara Chemical Industry Co., Ltd. Anilinopyrimidine derivatives. Patent US 4943675, 1990, A1.
  • Prakash, O.; Kumar, A.; Sadana, A.; Prakash, R.; Singh, S. P.; Claramunt, R. M.; Sanz, D.; Alkorta, I.; Elguero, J. Study of the reaction of chalcone analogs of dehydroacetic acid and o-aminothiophenol: Synthesis and structure of 1,5-benzothiazepines and 1,4-benzothiazines. Tetrahedron 2005, 61, 6642–6651.
  • Mokhtar, F.; Pascal, H.; Mohamed, A. Synthesis of 4-pyrano-1, 5-benzodiazepines catalysed by bismuth (III) derivatives. Res. J. Pharm. Bio. Chem. Sci. 2012, 3 (2), 10–15.
  • Fodili, M.; Amari, M.; Kolli, B.; Robert, A.; Baudy-Floch, M.; Le Grel, P. An efficient synthesis of new 2-pyronyl-1,5-benzodiazepine derivatives. Synthesis 1999, 5, 811–814.
  • El Abbassi, M.; Djerrari, B.; Essassi, E. M.; Fifani, J. L’acide dehydracetique, precurseur de synthese de benzodiazepines. Tetrahedron Lett. 1989, 30 (50), 7069–7070.
  • Bentley, R.; Zwitkowits, P. M. Biosynthesis of tropolones in Penicillium stipitatum, VII, 1,2: The formation of polyketide lactones and other nontropolone compounds as a result of ethionine inhibition. J. Am. Chem. Soc. 1967, 89, 676–680.
  • Bentley, R.; Zwitkowits, P. M. Biosynthesis of tropolones in Penicillium stipitatum, VIII, 1: The utilization of polyketide lactones for tropolone formation. J. Am. Chem. Soc. 1967, 89, 681–685.
  • Collie, J. N. The lactone of triacetic acid. J. Chem. Soc. 1891, 59, 607–617.
  • Aït-Baziz, N.; Rachedi, Y.; Silvac, A. M. S. Reactivity of some structural analogs of dehydroacetic acid with o-phenylenediamine. Arkivoc 2010, 10, 86–97.
  • Rehse, K.; Ruether, D. S-Oxidation and anticoagulant activity in 4-hydroxycoumarines, 4-hydroxy-2-pyrones, and 1,3-indanediones. Arch. Pharm. 1984, 317, 262–267.
  • Toray Industries, Inc. Ketone derivatives and their medical applications. Patent US6100292, 2000, A1.
  • Zaidan, H.; Biseibutsu, K.; Kenkyu, K. Derivatives of 6-methyl-2H-pyran-2,4(3H)-dione. Patent US3963756, 1976, A1.
  • Wiley, R. H.; Jarboe, C. H.; Ellert, H. G. 2-Pyrones, XV: Substituted 3-cinnamoyl-4-hydroxy-6-methyl-2-pyrones from dehydroacetic acid. J. Am. Chem. Soc. 1955, 77, 5102–5105.
  • Borsche, W.; Gerhardt, M. Untersuchungen über die Bestandteile der Kawa-Wurzel, I: Über Yangonin. Chem. Ber. 1914, 47, 2902–2918.
  • Prakash, O. M.; Kumar, A.; Sadana, A.; Singh, S. P. A facile synthesis of 3,4-dihydro-2-pyronyl-1,5-benzodiazepine derivatives. Synth. Commun. 2002, 32, 2663–2667.
  • Claramunt, R. M.; Sanz, D.; Aggarwal, S.; Kumar, A.; Prakash, O.; Singh, S. P.; Elguero, J. The reaction of o-phenylenediamine with α,β-unsaturated carbonyl compounds (06–2001GP). Arkivoc 2006, 14, 35–45.
  • Aît-Baziz, N.; Rachedi, Y.; Hamdi, M.; Silva, A. M. S.; Belagroune, F.; Thiery, R.; Sellier, N. 4-Hydroxy-6-methyl-3-(5-phenyl-2E,4E-pentadien-1-oyl)-2H-pyran-2-one: Synthesis and reactivity with amines. J. Heterocycl. Chem. 2004, 41, 587–591.
  • Aît-Baziz, N.; Rachedi, Y.; Chemat, F.; Hamdi, M. Solvent-free microwave-assisted Knoevenagel condensation of dehydroacetic acid with benzaldehyde derivatives: A rapid, clean and environmentally friendly approach. Asian J. Chem. 2008, 20, 2610–2622.
  • Rabahi, A.; Hamdi, S. M.; Rachedi, Y.; Hamdi, M.; Talhi, O.; Paz, F. A. A.; Silva, A. S. M.; Fadila, B.; Malika, H.; Kamel, T. 2D-NMR, x-ray crystallography and theoretical studies of the reaction mechanism for the synthesis of 1,5-benzodiazepines from dehydroacetic acid derivatives and o-phenylenediamines. J. Mol. Struct. 2014, 1061, 97–103.
  • Wiley, R. H.; Jarboe, C. H.; Ellert, H. G. 2-Pyrones, XV: Substituted 3-cinnamoyl-4-hydroxy-6-methyl-2-pyrones from dehydroacetic acid. J. Am. Chem. Soc. 1955, 77, 5102–5105.
  • Sosnovskikh, V. Ya.; Usachev, B. I.; Blinov, A. G.; Kodess, M. I. New derivatives of dehydroacetic acid: Synthesis of 2-polyfluoroalkyl-7-methylpyrano[4,3-b]pyran-4,5-diones. Mendeleev Commun. 2001, 11, 36–38.
  • Qamar, Y.; Siddiq, M. Synthesis of 2-aryl-7-methylpyrano[4,3-b]pyran-4(H),5(H)-diones. Indian J. Chem., Sect. B 1988, 27 (1–12), 373.
  • Traverso, G. Pyrones and derivatives. X. Nature of the thiocarbonyl group of the 4-thiopyrones. Annali di Chimica (Rome, Italy) 1955, 45, 695–705.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.