Preparation of C-(2-deoxyhex/pent-1-enopyranosyl)heterocycles.
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.
Mahmoud
S H
SH
Department of Organic Chemistry, Lajos Kossuth University, Debrecen, Hungary.
Somsák
L
L
Farkas
I
I
D003486:Cyanides; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D009904:Optical Rotation; D010069:Oxadiazoles / Q000138:chemical synthesis* / Q000737:chemistry; D012997:Solvents; D013237:Stereoisomerism; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry
D003486:Cyanides; D006027:Glycosides; D007202:Indicators and Reagents; D009705:Nucleosides; D010069:Oxadiazoles; D012997:Solvents; D013844:Thiazoles; D014230:Triazoles