One-pot synthesis of polyfunctionalized 4H-pyran derivatives bearing fluorochloro pyridyl moiety

Ye, Zhenjun; Xu, Renbo; Shao, Xusheng; Xu, Xiaoyong; Li, Zhong

doi:10.1016/j.tetlet.2010.07.065

Cited by 32 publications

(12 citation statements)

References 20 publications

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“…Based on our results and those reported in literatures [26,30,[38][39][40], we proposed a mechanism for the one-pot synthesis of polyfunctionalized 4H-pyrans from the condensation of aldehydes, malononitrile and an active methylene compound (Scheme 2). The surface O 2-ions of the solid superbase act as active basic sites to abstract H ?…”

Section: Plausible Reaction Mechanismsupporting

confidence: 65%

Novel MgO–SnO2 Solid Superbase as a High-Efficiency Catalyst for One-Pot Solvent-Free Synthesis of Polyfunctionalized 4H-pyran Derivatives

et al. 2012

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We report for the first time the hydrothermal synthesis of MgO-SnO 2 solid superbase using P123 as template. The basicity of the materials was determined by two approaches of Hammett indicators method and temperature-programmed desorption using CO 2 as adsorbate (CO 2 -TPD). It was found that Mg/Sn molar ratio has an effect on MgO-SnO 2 basicity, and superbasicity was observed only at Mg/Sn molar ratio of 1. With variation of Mg/Sn molar ratio, superbase strength (H -) was in the 26.5-33.0 range, showing superbasic value up to 0.939 mmol/g. The structure and texture of the as-prepared materials were studied by powder X-ray diffraction (XRD), scanning electron microscopy (SEM), and N 2 physioadsorption methods. We detected particles of spherical morphology having diameter of ca. 150 nm. N 2 adsorption-desorption results suggested that the materials are of mesoporous structure, having specific surface area of 115.2 m 2 /g and average pore diameter of 6 nm. The superbase was found to exhibit excellent catalytic activity towards the one-pot synthesis of polyfunctionalized 4H-pyrans through the condensation of aldehydes, malononitrile, and an active methylene compound. Its excellent catalytic efficiency is related to its superbasicity of the MgO-SnO 2 . The results provide a new route for the design and preparation of composite oxide superbases. Furthermore, the solid superbases will facilitate a strategy for high-efficiency synthesis of polyfunctionalized 4H-pyrans.

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Section: Plausible Reaction Mechanismsupporting

confidence: 65%

Novel MgO–SnO2 Solid Superbase as a High-Efficiency Catalyst for One-Pot Solvent-Free Synthesis of Polyfunctionalized 4H-pyran Derivatives

et al. 2012

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“…The reaction can occur via the initial formation of the intermediate acrylonitrile derivative A followed by its nucleophilic attack of the anion of the acetoacetanilide derivatives to produce the intermediate B. The final products D were formed via the initial cyclization and subsequent tautomerization of the cyclic intermediate C. 22) To survey the scope of this reaction for the synthesis of 4H-pyran and 1,4-dihydropyridine derivatives, different catalyst was used. Thus, the multicomponent reaction of acetoacetani-lide 1a or b with either 2a, b, c or d and 3 in absolute ethanol containing a catalytic amount of ammoniumacetate gave the 1,4-dihydropyridine derivatives 5a-g, respectively (Chart 3).…”

Section: Resultsmentioning

confidence: 99%

Multicomponent Reactions of Acetoacetanilide Derivatives with Aromatic Aldehydes and Cyanomethylene Reagents to Produce 4<i>H</i>-Pyran and 1,4-Dihydropyridine Derivatives with Antitumor Activities

Azzam

Mohareb

2015

Chem. Pharm. Bull.

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The multi-component reaction of either acetoacetanilide derivative 1a or b with any of the aldehyde derivatives 2a-d and malononitrile 3 in the presence of triethylamine as a catalyst gave the 4H-pyran derivatives 4a-g, respectively. Carrying the same reaction but using a catalytic amount of ammonium acetate gave the 1,4-dihydropyridine derivatives 5a-f, respectively. The use of ethyl cyanoacetate instead of malononitrile in the presence of a catalytic amount of triethylamine gave the 4H-pyran derivatives 7a-d, respectively. Compound 4e was used to synthesize 1,4-dihydropyridine 9a-c and arylhydraone 11a-e derivatives were synthesized from 4a and e. The anti-tumor evaluations of the newly synthesized products were tested against six human cancer and normal cell lines. The results showed that compounds 4a, b, f, 5d, f, 9 and 11a-d had optimal cytotoxic effect against cancer cell lines with IC 50 <550 nM. The toxicity of the most active compounds was further measured against shrimp larvae.Key words 4H-pyran; 1,4-dihydropyridine; cyanomethylene; cytotoxicity Multicomponent reactions (MCRs) are one-pot reactions employing more than two starting materials, e.g. 3, 4, ... , 7, where most of the atoms of the starting materials are incorporated in the final product.1) Several descriptive tags are regularly attached to MCRs they are atom economic, e.g. the majority if not all of the atoms of the starting materials are incorporated in the product; they are efficient, e.g. they efficiently yield the product since the product is formed in onestep instead of multiple sequential steps; they are convergent, e.g. several starting materials combine in one reaction to form the product; they exhibit a very high bond-forming-index (BFI), e.g. several non-hydrogen atom bonds are formed in one synthetic transformation.2,3) Therefore MCRs are often a useful alternative to sequential multistep synthesis.In view of the increasing interest in the preparation of a large variety of heterocyclic compound libraries, the development of new synthetically valuable MCRs with several diversity points remains a challenge for both academic and industrial institutions.4) 4H-Pyran and its derivatives are an important class of heterocyclic compounds possessing broad biological activities, such as anti-inflammatory, 5) analgesic, 6) antioxidant,antiamoebic 11) and oral analgesic. 12) From the aforementioned reports, it seemed that the development of an efficient, rapid, and clean synthetic route towards focused libraries of such compounds is of great importance to both medicinal and synthetic chemists. The combination of multicomponent reactions (MCR 2 ), [13][14][15] which combines different types of MCRs in one pot process inheriting the high selectivity, efficiency, and atom economy of MCR, has gained more and more attention, since Dömling and Ugi reported the first MCR 2 of a modified four-component reaction (4CR) and the Ugi 4CR.16) However, most of the reported MCR 2 cases are limited in isonitrile based multicomponent reactions. [17][18][19][20]...

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“…In addition, the title compound and its derivatives have been used as potential precursors to prepare 5,7-diazaspiro-[2,5]octane (Elinson et al, 2010), 2-amino-4H-chromene-3-carbonitrile (Ding et al, 2010) and 4H-pyran derivatives (Ye et al, 2010).…”

Section: Related Literaturementioning

confidence: 99%

2-(4-Nitrobenzylidene)malononitrile

et al. 2012

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One-pot synthesis of polyfunctionalized 4H-pyran derivatives bearing fluorochloro pyridyl moiety

Cited by 32 publications

References 20 publications

Novel MgO–SnO2 Solid Superbase as a High-Efficiency Catalyst for One-Pot Solvent-Free Synthesis of Polyfunctionalized 4H-pyran Derivatives

Novel MgO–SnO2 Solid Superbase as a High-Efficiency Catalyst for One-Pot Solvent-Free Synthesis of Polyfunctionalized 4H-pyran Derivatives

Multicomponent Reactions of Acetoacetanilide Derivatives with Aromatic Aldehydes and Cyanomethylene Reagents to Produce 4<i>H</i>-Pyran and 1,4-Dihydropyridine Derivatives with Antitumor Activities

2-(4-Nitrobenzylidene)malononitrile

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