European Journal of Chemistry 2011, 2(4), 552-557. doi:10.5155/eurjchem.2.4.552-557.265

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, Accepted: 04 Nov 2010, Published: 31 Dec 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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Keywords


Quinuclidinone; Mannich bases; Ring expansion; C-Nucleosides; Spiro derivative; Quinuclidine sugar

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DOI: 10.5155/eurjchem.2.4.552-557.265

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How to cite


Hamama, W.; Zoorob, H.; El-Magid, O. Eur. J. Chem. 2011, 2(4), 552-557. doi:10.5155/eurjchem.2.4.552-557.265
Hamama, W.; Zoorob, H.; El-Magid, O. Fused and spiro nitrogen heterocycles of quinuclidine and its C-nucleosides. Eur. J. Chem. 2011, 2(4), 552-557. doi:10.5155/eurjchem.2.4.552-557.265
Hamama, W., Zoorob, H., & El-Magid, O. (2011). Fused and spiro nitrogen heterocycles of quinuclidine and its C-nucleosides. European Journal of Chemistry, 2(4), 552-557. doi:10.5155/eurjchem.2.4.552-557.265
Hamama, Wafaa, Hanafi Hassan Zoorob, & Osama Abd El-Magid. "Fused and spiro nitrogen heterocycles of quinuclidine and its C-nucleosides." European Journal of Chemistry [Online], 2.4 (2011): 552-557. Web. 16 Sep. 2019
Hamama, Wafaa, Zoorob, Hanafi, AND El-Magid, Osama. "Fused and spiro nitrogen heterocycles of quinuclidine and its C-nucleosides" European Journal of Chemistry [Online], Volume 2 Number 4 (31 December 2011)

DOI Link: https://doi.org/10.5155/eurjchem.2.4.552-557.265

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