Preparation of C-(2-deoxyhex/pent-1-enopyranosyl)heterocycles

Saad H. Mahmoud, László Somsák, István Farkas

Research output: Contribution to journalArticle

34 Citations (Scopus)

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 1,3-di-azabicyclo[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)benzothiazole. Several 2-(per-O-acetylhexo/pentopyranosyl)benzothiazoles also gave 2-(per-O-acetyl-2-deoxyhex/pent-1-enopyranosyl)benzothiazoles 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)tetrazole 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-substituted-1,3,4-oxadiazoles.

Original languageEnglish
Pages (from-to)91-104
Number of pages14
JournalCarbohydrate Research
Volume254
Issue numberC
DOIs
Publication statusPublished - Feb 17 1994

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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