Synthesis and rearrangement of cycloalkyl[1,2-e]oxazolo[3,2-a]pyrimidin-8/9-ones: an access to cycloalkyl[1,2-d]oxazolo[3,2-a]pyrimidin-5-ones

Adetchessi, Ouro-Sama; Léger, Jean‐Michel; Guillon, Jean; Forfar‐Bares, Isabelle; Bosc, Jean-Jacques; Jarry, Christian

doi:10.1016/j.tet.2005.02.079

Cited by 5 publications

(3 citation statements)

References 15 publications

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“…Thus, a NOE effect between the H-3 0 arabinose proton and one methylene proton of the fused cyclohexyl moiety was observed for compound 13, while no correlation was observed between the two corresponding protons in 12 [9]. On the other hand, compound 13 was obtained after dehydration when the two nitrogen atom attacks order was reversed.…”

Section: Chemistrymentioning

confidence: 93%

“…Diethyl ethoxymethylene malonate (DEEM) is a well-known bis-electrophile reagent used for heterocyclic ring annelation [9,17]. Diethyl ethoxymethylene malonate (DEEM) is a well-known bis-electrophile reagent used for heterocyclic ring annelation [9,17].…”

Section: Chemistrymentioning

confidence: 99%

“…Amongst them new antimetabolite pyrimidine analogues, i.e. We already developed this approach for obtaining various bicyclic compounds [7][8][9]. 1).…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and in vitro cytostatic activity of new β - d -arabino furan[1′,2′:4,5]oxazolo- and arabino-pyrimidinone derivatives

Bosc

Latxague

Léger

et al. 2010

European Journal of Medicinal Chemistry

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A series of nucleoside derivatives was obtained via heteroatom annulation of the amino oxazoline of D-(-)-arabinose. Unequivocal proofs for the stereostructure of some new arabinosyl pyrimidinone derivatives were obtained by X-ray structure analysis. These newly synthesized compounds were then evaluated for their cytostatic activity against murine leukemia (L1210), and human T-lymphocytes (Molt 4/C8 and CEM). Of all the compounds in the series, the protected silylated tricyclic fused pyrimidinone 10 showed the most significant antitumor activity against murine leukemia L1210 (IC(50)=6 microM), and human T-lymphocytes cells Molt 4/C8 (IC(50)=7.9 microM) and CEM/0 cell lines (IC(50)=7.5 microM). None of the compounds exhibited significant antiviral inhibitory activities.

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Section: Chemistrymentioning

confidence: 93%

Section: Chemistrymentioning

confidence: 99%

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Synthesis and in vitro cytostatic activity of new β - d -arabino furan[1′,2′:4,5]oxazolo- and arabino-pyrimidinone derivatives

Bosc

Latxague

Léger

et al. 2010

European Journal of Medicinal Chemistry

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Synthesis and Rearrangement of Cycloalkyl[1,2‐e]oxazolo[3,2‐a]pyrimidin‐8/9‐ones: An Access to Cycloalkyl[1,2‐d]oxazolo[3,2‐a]pyrimidin‐5‐ones.

et al. 2005

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Fused pyrimidine derivatives R 0515 Synthesis and Rearrangement of Cycloalkyl[1,2-e]oxazolo[3,2-a]pyrimidin-8/9-ones: An Access to Cycloalkyl[1,2-d]oxazolo[3,2-a]pyrimidin-5-ones. -The one-step ring-annulation of oxazolines (I) with oxocyclohexanecarboxylate (II) at room temperature gives oxazolopyrimidinones (III). These compounds can be easily dehydrated to provide the corresponding pyrimidinones (IV). In refluxing xylene, the same reaction leads to isomeric pyrimidinones (IV)/(V) and (VII)/(VIII), respectively. -(ADETCHESSI, O.-S.; LEGER, J.-M.; GUILLON, J.; FORFAR-BARES, I.; BOSC, J.-J.; JARRY*, C.; Tetrahedron 61 (2005) 18, 4453-4460; Pharmacochim., Univ. Victor Segalen, F-33076 Bordeaux, Fr.; Eng.) -Bartels 36-150

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Crystal structure and identification of a pyrimido[6,1-b][1,3]oxazin-6-one derivative from the reaction of acrolein with 5-(phenoxymethyl)-2-amino-2-oxazoline

Guillon

Rubio

Savrimoutou

et al. 2018

Comptes Rendus. Chimie

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Synthesis and rearrangement of cycloalkyl[1,2-e]oxazolo[3,2-a]pyrimidin-8/9-ones: an access to cycloalkyl[1,2-d]oxazolo[3,2-a]pyrimidin-5-ones

Cited by 5 publications

References 15 publications

Synthesis and in vitro cytostatic activity of new β - d -arabino furan[1′,2′:4,5]oxazolo- and arabino-pyrimidinone derivatives

Synthesis and in vitro cytostatic activity of new β - d -arabino furan[1′,2′:4,5]oxazolo- and arabino-pyrimidinone derivatives

Synthesis and Rearrangement of Cycloalkyl[1,2‐e]oxazolo[3,2‐a]pyrimidin‐8/9‐ones: An Access to Cycloalkyl[1,2‐d]oxazolo[3,2‐a]pyrimidin‐5‐ones.

Crystal structure and identification of a pyrimido[6,1-b][1,3]oxazin-6-one derivative from the reaction of acrolein with 5-(phenoxymethyl)-2-amino-2-oxazoline

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