Synthesis and biological properties of some heterocyclic derivatives of guanidine

Shvedov, V. I.; Vasil'eva, V. F.; Korsakova, I. Ya.; Galitsina, V. A.; Medvedev, B. A.; Novitskaya, N. A.; Lapaeva, N. B.; Pershin, G. N.; Mashkovskii, M. D.

doi:10.1007/bf00765834

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4-ethano-810-dimethyl-1810-triaza-spiro[55] Undecan-5-1

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“…: 240 °C. 1 10. 1,2,3,4,5,6,7,8-Octahydro-9-(1,2,3,4,5-pentahydroxy-1-pent-1-yl)-10-oxa-1,8-diaza-1,4 …”

Section: 4-ethano-810-dimethyl-1810-triaza-spiro[55] Undecan-5-mentioning

confidence: 99%

See 1 more Smart Citation

Fused and spiro nitrogen heterocycles of quinuclidine and its C-nucleosides

Hamama¹,

Zoorob²,

El-Magid³

2011

Eur. J. Chem.

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KEYWORDSQuinuclidin-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.

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“…: 240 °C. 1 10. 1,2,3,4,5,6,7,8-Octahydro-9-(1,2,3,4,5-pentahydroxy-1-pent-1-yl)-10-oxa-1,8-diaza-1,4 …”

Section: 4-ethano-810-dimethyl-1810-triaza-spiro[55] Undecan-5-mentioning

confidence: 99%

“…Quinuclidine is a part of the structure of a number of natural physiologically active compounds and synthetic drugs [1][2][3]. Some functionalized synthetic quinuclidines have also been identified as specific muscarinic agonists with potential in Alzheimer's dementia therapy [4,5].…”

Section: Introductionmentioning

confidence: 99%