Synthesis and molecular structure of new acyclic analogues of nucleotides with a 1,2-alkadienic skeleton.
Reaction of 1-chloro-4-(diethoxyphosphonyl)alka-2,3-dienes 14,15 with purine and pyrimidine heterocyclic bases in the presence of cesium carbonate afforded new acyclic analogues of nucleotides containing a 1,2-alkadienic skeleton 18-23. Dealkylation of 18-23 furnished phosphonic acids 2a-f. In contrast, alkylation reaction with 1-chloro-4-(diethoxyphosphonyl)octa-2,3-diene 16 led to Z- and E-1,3-alkadienic phosphonates 25a,b and 26a,b. A similar reaction with 1-chloro-4-(diethoxyphosphonyl)-2-methylbuta-2,3-diene 17 led to the elimination of hydrochloride and formation of 4-(diethylphosphonyl)-2-methylbut-1-en-3-yne 24. Molecular structures of new acyclic nucleotides 18 and 2f are determined by X-ray crystallographic analysis.
Brel
Valery K
VK
Institute of Physiologically Active Compounds, Russian Academy of Sciences, Chernogolovka, Moscow Region, 142432, Russian Federation. brel@ipac.ac.ru
Belsky
Vitaly K
VK
Stash
Adam I
AI
Zavodnik
Valery E
VE
Stang
Peter J
PJ
D000466:Alkadienes / Q000737:chemistry*; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D009711:Nucleotides / Q000138:chemical synthesis* / Q000737:chemistry*
D000466:Alkadienes; D009711:Nucleotides