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Armas, Héctor Novoa de; Blaton, N. M.; Peeters, O. M.; Ranter, C. J. De; Suárez, Margarita; Ochoa, Estael; Verdecia, Yamila; Salfrán, Esperanza

doi:10.1023/a:1009535215383

Cited by 14 publications

(5 citation statements)

References 11 publications

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“…Analogous to the known Knoevenagel condensation [14,15,16,17,18], we found that the reaction of ethyl cyanoacetate with p -methoxybenzaldehyde ( 7 ) in the presence of acetic acid and pyrrolidine generated an excellent yield (98%) of the desired product 8 in Scheme 2. This result suggests that ethyl cyanoacetate has better reactivity due to its relatively high α-proton acidity.…”

Section: Resultssupporting

confidence: 61%

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Total Synthesis of Flocoumafen via Knoevenagel Condensation and Intramolecular Ring Cyclization: General Access to Natural Products

et al. 2012

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The total synthesis and structure determination of cis- and trans-flocoumafen was described. The key synthetic steps involve Knoevenagel condensation with p-methoxybenzaldehyde, in situ decarboxylation and intramolecular ring cyclization to construct the tetralone skeleton. Stereospecific reduction of the O-alkylated ketone 13 afforded good yield of precusor alcohol 5. Final coupling of alcohol 5 with 4-hydroxy-coumarin yielded flocoumafen (1). Separation and structure determination of cis- and trans-flocoumafen through 2D NMR analyses-assisted computer simulation techniques for the evaluation of anticoagulant activities are reported for the first time. This method is useful for generating the core tetralone skeleton of 4-hydroxycoumarin derivatives and provides a generalized access to various warfarin type anticoagulants.

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Section: Resultssupporting

confidence: 61%

“…The organic layer was dried over anhydrous MgSO 4 , filtered, and evaporated under reduced pressure. The crude was purified by flash column chromatography (silica gel, ethyl acetate/ n -hexane 1:2, v/v) to give pure product 8 [14,15,16,17,18] in 98% yield. Yellow solid.…”

Section: Methodsmentioning

confidence: 99%

Total Synthesis of Flocoumafen via Knoevenagel Condensation and Intramolecular Ring Cyclization: General Access to Natural Products

et al. 2012

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“…Several 5-arylidene-2,2-dimethyl-1,3-dioxane-4,6-diones (Huck et al, 1995;Gould et al, 1998;Novoa de Armas et al, 2000;O'Leary et al, 2001;O'Leary & Wallis 2006;Crawford & McNab, 2009;Wilsily & Fillion, 2009;Zeng, 2010aZeng, ,b, 2011aZeng, ,b,c, 2013Jie, 2012;García-Á lvarez et al, 2013;Dey et al, 2015) and their spiro-analogues (Sato et al, 1989;Zeng, 2011d,e,f; Zeng et al 2013) have been characterized by X-ray analysis. However, information on the crystal structure of 5-arylmethylidene-2,2-dimethyl-1,3-dioxane-4,6-diones containing an amino functionality on the aromatic ring is not available.…”

Section: Database Surveymentioning

confidence: 99%

Crystal structure of 5-[4-(diethylamino)benzylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione

Stepina¹,

Stepanovs²,

Mieriņa³

et al. 2015

Acta Cryst E

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“…Besides, thieno[2,3b]pyridines with a different substitution pattern have shown interesting antimicrobial effects (Badr et al, 1991). In a previous study, we reported the crystal structure of 2,5-diethoxycarbonyl-6-methyl-4-phenylthieno[2,3-b]pyridine (Novoa de Armas et al, 2003). The title compound, (I), is a 4-(4-bromophenyl)-substituted thieno[2,3-b]pyridine, obtained by the reaction of ethyl 4-(4-bromophenyl)-6-chloro-5-formyl-2-methyl-1,4-dihydropyridine-3-carboxylate (Verdecia et al, 1996) with an equimolar amount of ethyl mercaptoacetate in the presence of sodium ethoxide and dry ethanol.…”

Section: Commentmentioning

confidence: 99%