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Preparation of C-(2-deoxyhex/pent-1-enopyranosyl)heterocycles
S H Mahmoud1, L Somsák, I Farkas
1Department of Organic Chemistry, Lajos Kossuth University, Debrecen, Hungary.
Abstract:
Acetylated 1-cyanoglycals (2,6-anhydro-3-deoxyhept/hex-2-enononitriles) were prepared by direct elimination of acetic acid from the appropriate acetylated 2,6-anhydrohept/hexononitriles with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in aprotic solvents. Heterocyclisation of the cyano group of acetylated 1-cyano-D-galactal with 2-aminothiophenol led to 2-(3,4,6-tri-O-acetyl-2-deoxy-D-lyxo-hex-1-enopyranosyl)benz othiazole. Several 2-(per-O-acetylhexo/pentopyranosyl)benzothiazoles also gave 2-(per-O-acetyl-2-deoxyhex/pent-1-enopyranosyl)benzothiazole s with DBU. 3-(Per-O-acetylhexo/pentopyranosyl)-[1,2,4]triazolo[4,3-a] pyrimidines rearranged with DBU to the corresponding acetylated 2-glycosyl-[1,2,4]triazolo[1,5-a]pyrimidines. By the reaction of 1-cyano-D-galactal with ammonium azide, 2-(3,4,6-tri-O-acetyl-2-deoxy-D-lyxo-hex-1-enopyranosyl)tetr azole was prepared and then transformed with carboxylic acid derivatives into 2-(3,4,6-tri-O-acetyl-2-deoxy-D-lyxo-hex-1-enopyranosyl)-5-s ubstituted-1,3,4- oxadiazoles.