W. Hamama, H. H. Zoorob, O. M. A. El‐Magid
Dec 31, 2011
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Journal
European Journal of Chemistry
Abstract
Quinuclidin-3-one ( 1 ) was used as a versatile intermediate for the synthesis of fused and spiro quinuclidine and its C -nucleosides. The reaction of 1 with formalin and secondary amines namely; morpholine, piperidine, and piperazine afforded the corresponding Mannich bases 2 - 4 in acid medium. Quinuclidino[3,2- b ]pyran 5 has been synthesized via a selective cyclocondensation reaction between Mannich base of quinuclidinone hydrochloride 2 and malononitrile. The transformation of 1 with formalin and methylamine in molar ratio (1:20:2) afforded the spiro compound 7 . Ring expansion of 2 under Schmidt reaction conditions gave the 1,3-diazabicyclo[3.2.2]nonanone derivative 6 . Eventually, the synthesis of C -nucleosides 10 , 12 - 14 were achieved by using aldohexoses and aldopentose catalyzed by zinc chloride, while, the bis -quinuclidine derivative 15 was obtained by using sodium carbonate. Newly synthesized compounds were characterized by IR, 1 H NMR, and mass spectral data.