First synthesis of double headed 1,3,4-oxadiazino[6,5-b]indole acyclo C-nucleosides.
Condensation of 1,3-dihydro-2,3-dioxo-2H-indoles (la-c) with galactaric acid bis hydrazide (2) gave the corresponding galactaric acid bis[2-(1,2-dihydro-2-oxo-3H-indol-3-ylidene)hydrazides] (3a-c). Acetylation of the latter compounds with acetic anhydride in the presence of pyridine at ambient temperature gave the 2,3,4,5-tetra-O-acetylgalactaric acid bis[2-(1,2-dihydro-2-oxo-1-substituted-3H-indol-3-ylidene)hydrazides] (4b-d). Heterocyclization of the tetra-O-acetates 4b-d by heating with thionyl chloride afforded the double headed acyclo C-nucleosides: 1,2,3,4-tetra-O-acetyl- 1,4-bis[9-substituted-1,3,4-oxadiazino[6,5-b]indol-2-yl-1-ium]-galacto-tetritol dichlorides (5b-d). Structures of the prepared compounds were elucidated from their spectral properties.
Nasr
Adel Z
AZ
Department of Chemistry, Faculty of Science, Cairo University, Faiyoum, Egypt. adelznasr@hotmail.com
D000107:Acetylation; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis*; D010078:Oxazines / Q000138:chemical synthesis / Q000737:chemistry*
C500097:1,3,4-oxadiazino(6,5-b)indole; D007211:Indoles; D009705:Nucleosides; D010078:Oxazines