ISSN:
0021-8383
Schlagwort(e):
Chemistry
;
Organic Chemistry
Quelle:
Wiley InterScience Backfile Collection 1832-2000
Thema:
Chemie und Pharmazie
Notizen:
Oxidative cyclization of D-galactose (p-chlorophenyl)thiosemicarbazone gave 2-(p-chloroanilino)-5-(D-galacto-1,2,3,4,5-pentahydroxypentyl)-1,3,4-thiadiazole (1), whose acetylation afforded 2-[N-acetyl-N-(p-chlorophenyl)]-amino-5-(D-galacto-1,2,3,4,5-pentacetoxypentyl)- 1,3,4-thiadiazole (3). Its periodate oxidation of the glycol groups gave 2-(p-chloroanilino)-1,3,4-thiadiazole-5-carboxaldehyde (4), which can be transformed into 1,2-[2-(p-chloroanilino)-1,3,4-thiadiazol-5-yl]-1-hydroxy-2-oxoethane. A number of hydrazones of the formyl thiadiazole was prepared and its reduction with sodium borohydride gave 2-(p-chloroanilino)-5-hydroxymethyl-1,3,4-thiadiazole (6), whose acetylation gave a mono-O-acetyl derivative (7). Oxidation of the formyl thiadiazole gave 2-(p-chloroanilino)-1,3,4-thiadiazole (9). The spectral data of the compounds were discussed.
Materialart:
Digitale Medien
URL:
http://dx.doi.org/10.1002/prac.19863280102
