Synthesis and Characterization of some Heterocyclic Derivatives by Cyclization of Carbohydrate Thiosemicarbazones. Part I

We report the synthesis of 2,3-dihydro-1,3,4-thiadiazoles and 1,3,4-thiadiazoles from 1,2:3,4-di-O-isopropylidene-α-D-galacto-1,6-hexodialdo-1,5-pyranose thiosemicarbazone. The physical and spectroscopic characterizations of the heterocyclic derivatives as well as the intermediate product are descri...

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Autor principal: Martins Alho, M.A
Otros Autores: D'Accorso, N.B
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: 1997
Acceso en línea:Registro en Scopus
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245 1 0 |a Synthesis and Characterization of some Heterocyclic Derivatives by Cyclization of Carbohydrate Thiosemicarbazones. Part I 
260 |c 1997 
270 1 0 |m Martins Alho, M.A.; Ctro. de Invest. de Hidratos de C., Depto. de Quim. Orgánica, Pabellón II, 3 Piso, C. P. 1428, Buenos Aires, Argentina 
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504 |a Nelson, J.A., Rose, L.M., Bennett, L.L., (1976) J. Cancer Res., 36, p. 1375 
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504 |a Miller, W.H., Dessert, A.M., Roblin, R.O., (1950) J. Am. Chem. Soc., 72, p. 4893 
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504 |a El Ashry, E.S., Nassr, M.A., El Kilany, Y., Mousaad, A., (1987) Bull. Chem. Soc. Japan, 60 (9), p. 3405 
504 |a Martins Alho, M.A., D'Accorso, N.B., Thiel, I.M.E., (1996) J. Heterocyclic Chem., 33, p. 1339 
504 |a Lough, C., Hindsgaul, O., Lemieux, R., (1983) Carbohydr. Res., 120, p. 43 
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504 |a PCMODEL for Windows 5.1 (1994) Serena Software, , MM+ Force Field 
504 |a (1995) Hyperchem, , PM3 Force Field 
504 |a Tronchet, J.M.J., Neeser, J.R., Charollais, E.J., González, L., (1983) J. Carbohydr. Chem., 2, p. 19 
520 3 |a We report the synthesis of 2,3-dihydro-1,3,4-thiadiazoles and 1,3,4-thiadiazoles from 1,2:3,4-di-O-isopropylidene-α-D-galacto-1,6-hexodialdo-1,5-pyranose thiosemicarbazone. The physical and spectroscopic characterizations of the heterocyclic derivatives as well as the intermediate product are described. We present the prefered conformation in solution using computational calculations and spectroscopic data. The possibilities of chiral induction of the cyclization reaction are discussed.  |l eng 
593 |a Ctro. de Invest. de Hidratos de C., Depto. de Quim. Orgánica, Pabellón II, 3 Piso, C. P. 1428, Buenos Aires, Argentina 
700 1 |a D'Accorso, N.B. 
773 0 |d 1997  |g v. 34  |h pp. 1415-1419  |k n. 5  |p J. Heterocycl. Chem.  |x 0022152X  |w (AR-BaUEN)CENRE-780  |t Journal of Heterocyclic Chemistry 
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