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Fused and spiro nitrogen heterocycles of quinuclidine and its C-nucleosides
Wafaa S. Hamama (1,*)
, Hanafi Hassan Zoorob (2) , Osama Abd El-Magid (3) (1) Department of Chemistry, Faculty of Science, Mansoura University, Mansoura, ET-35516 Egypt
(2) Department of Chemistry, Faculty of Science, Mansoura University, Mansoura, ET-35516, Egypt
(3) Department of Chemistry, Faculty of Science, Mansoura University, Mansoura, ET-35516, Egypt
(*) Corresponding Author
Received: 28 Aug 2010 | Revised: 27 Jun 2011 | Accepted: 04 Nov 2010 | Published: 31 Dec 2011 | Issue Date: December 2011
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, 1H NMR, and mass spectral data.
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DOI: 10.5155/eurjchem.2.4.552-557.265
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DOI Link: https://doi.org/10.5155/eurjchem.2.4.552-557.265
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European Journal of Chemistry 2011, 2(4), 552-557 | doi: https://doi.org/10.5155/eurjchem.2.4.552-557.265 | Get rights and content
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