A new route of synthesis of 3a,6a-Dihydro-oxazolo[5,4-d]oxazole derivatives

Synthetic Communications

Volumn 33, Issue 10, 2003, Pages 1675-1682

  Tapsoba, I ^a   Adhoum, N ^a   Ben Khoud, M L ^a   Kossai, R ^a   Boujlel, K ^a  

^a FACULTÉ DES SCIENCES DE TUNIS   (Tunisia)

Author keywords

[No Author keywords available]

Indexed keywords

3A,6A DIHYDROOXAZOLO[5,4 D]OXAZOLE; IMIDE; MERCURY; OXAZOLE DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CONTROLLED STUDY; CRYSTAL STRUCTURE; CYCLIC POTENTIOMETRY; CYCLIZATION; DIMERIZATION; ELECTROCHEMISTRY; ELECTRODE; ELECTROLYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0038244841     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120018929     Document Type: Article

References (21)

1. Kodama, Y.; Imoto, M.; Ohta, N.; Kitani, A.; Ito, S. Selective reduction of acetophenone to 1-phenylethanol in aqueous media. J. Electroanal. Chem. 2001, 507 (1-2), 103-109.
2. Fussing, I.; Güllu, M.; Hammarich, O.; Hussain, A.; Nielsen, M.F.; Utley, J.H.P. Stereoselective and mechanism in the electrohydrodimerisation of esters of cinnamic acid. J. Chem. Soc. Perkin Trans. 2 1996, 649.
3. Utley, J.H.P.; Smith, C.Z.; Motevalli, M. Electroorganic reactions. Part 51. Reactivity and stereochemical pathways for cathodically generated radical-anions of α,β-unsaturated ketones in aqueous media. J. Chem. Soc. Perkin Trans. 2 2000, 1053-1057.
4. Wei-Dong; Chi, Y.; An-Xing, W. A novel method to convert ketones and alehydes to the corresponding alcohols. Synth. Commun. 1998, 28 (15), 2827-2830.
5. Schwientek, M.; Pleus, S.; Hamann, C.H. Enantioselective electrodes: stereoselective electroreduction of 4-methylbenzophenone and acephenone. J. Electroanal. Chem. 1999, 461 (1-2), 94-101.
6. Miller, D.; Mandel, L.; Day, R.A., Jr. Electrochemical dimerisation of 3-methylcrotonaldehyde. J. Org. Chem. 1971, 36 (12), 1683-1685.
7. Kossai, R.; Tallec, A.; Hajjem, B.; Baccar, B. Cathodic behavior of aromatic ketones orthosubstitued with an imino-ether group. Preparation of nitrogen heterocyclic compounds. Electrochimica. Acta. 1991, 36 (1-2), 2019-2023.
8. Johnston, J.C.; Faulkner, J.D.; Mandel, L.; Day, R.A., Jr. Electrochemical reduction of geranial, farsenal and crotonaldehyde. J. Org. Chem. 1976, 41 (15), 2611-2614.
9. Fussing, I.; Hammarich, O.; Hussain, A.; Nielsen, M.F.; Utley, J.H.P. The influence of solvent on the mechanism and stereo-chemistry of electrodimerisation. The reduction of cinnamic acid esters in methanol. Acta. Chem. Scand. 1998, 52 (3), 328-337.
10. Klemm, J.H.; Olso, D.R. Electroreduction of α,β-unsaturated esters. II: synthesis of 2,3-diaryl-5-oxocyclopentane-1-carboxylates by hydrodimerisation of cinnamates. J. Org. Chem. 1973, 38 (19), 3390-3394.
11. Lai-Hao, W.; Shih-Wen, T. Direct determination of D-panthenol and salt of panthothenic acid in cosmetic and pharmaceutical preparations by differential pulse voltammetry. Anal. Chim. Acta. 2001, 432, 39-42.
12. Deprez, D.; Margraff, R.; Bizot, J.; Pulicani, J.P. Réduction electrochimique de la fonction amide composé antitumoral, l'échinosporine. Tetrahedron Lett. 1987, 28 (40), 4679-4680.
13. Benkeser, R.A.; Watanabe, H.; Mels, S.J.; Sabol, M.A. A new electrochemical method for the selective reduction of aliphatic amide to aldehydes or alcohols. J. Org. Chem. 1970, 35 (5), 1210-1211.
14. Hajjem, B.; Harizi, A.; Baccar, B. Action des alcools sur les arylimidates et phénylacétimidates N-acylés. Voie d'accès aux N-(aryl ou benzyldialcoxyméthyl)amides. J. Soc. Chim. Tunisie. 1994, 3 (8), 505-511.
15. Zinola, C.F.; Rodriguez, J.L.; Arevalo, M.C.; Pastor, E. A DEMS study of the electroreduction and oxidation of 3-buten-2-one and 2-butanone adsorbates on platinium. J. Electroanal. Chem. 1998, 454 (1-2), 161-172.
16. De Azevedo, D.C.; Boodts, J.F.C.; Cavalcanti, J.C.M.; Santana, A.E.G.; Dos Santos, A.S.; Bento, E.S.; Tonholo, J.; Goulart, M.O.F. Self protonation mechanism in the electrochemical reduction of jatrophone. J. Electroanal. Chem. 1999, 466 (1-2), 99-106.
17. Tapsoba, I.; Adhoum, N.; Benkhoud, M.L.; Kossai, R.; Boujlel, K. unpublished results.
18. Lange-Asschenfeldt, B.; Weninger, W.; Velasco, P.; Kyriakides, T.R.; Von Andrian, U.H.; Bornstein, P.; Detmar, M. Increased and prolonged inflammation and angiogenesis in delayed-type hypersensitivity reactions elicited in the skin of thrombospondin-2-deficient mice. Immunobiology 2002, 99 (2), 538-545.
19. Havard, J.M.; Yoshida, M.; Pasini, D.; Vladimirov, N.; Fréchet, J.M.J.; Medeiros, D.R.; Patterson, K.; Yamada, S.; Wilson, C.G.; Byers, J.D. Design of photoresist with reduced environmental impact. 2. Water-soluble resists based on photocrosslinking of poly(2-isopropenyl-2-oxazoline). J. Poly. Sci. A 1999, 37, 1225-1236.
20. Williams, D.R.; Brooks, D.A.; Meyer, K.G. Regioselective ring metalation in [2,4]bisoxazoles. Tetrahedron Lett. 1998, 39 (44), 8023-8026.
21. Baccar, B.; Mathis, F. Action of N-acyl and N-ethoxycarbonyl derivatives of imino ether on hydrazines and hydroxylamines. C. R. Acad. Sci. Paris 1965, 261, 174-177.