The first asymmetric synthesis of polyfunctionalized 4H-pyrans via Michael addition of malononitrile to 2-acyl acrylates

González, Rafael; Martín, Nazario; Seoane, Carlos; Marco, J. L.; Albert, Armando; Cano, F. H.

doi:10.1016/0040-4039(92)80031-e

Cited by 22 publications

(16 citation statements)

References 11 publications

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“…After acheiving the elusive enantioselectivity, we were excited to study the scope of our protocol for other aldehydes as well ( Table 6). The reaction of 4-chlorobenzaldehyde, 85 malononitrile and acetylacetone under optimized condition resulted in formation of the corresponding pyran derivative 2 in excellent yield with 79% ee. Similarly, the reaction of benzaldehyde, malononitrile and acetylacetone under our reaction conditions also gave excellent yield of the product with an excellent optical purity (enantiomeric excess of more 5 than 99%) as confirmed from the HPLC analysis.…”

Section: Resultsmentioning

confidence: 99%

Beyond enzymatic promiscuity: asymmetric induction by l-proline on lipase catalyzed synthesis of polyfunctionalized 4H-pyrans

2015

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We report herein the synthesis of polysubstituted 4H-pyrans 5 catalysed by PPL via a three-component reaction of aldehyde, malononitrile and acetyl acetone. The catalytic activity of PPL with other lipases and its reactivity profile in different reaction medium was thoroughly studied. Although the change in enzyme reaction specificity induced by metal substitutions and 10 amino acids is well known, non-covalent introduction of an amino acid into enzymatic promiscuous reaction to achieve stereoselectivity through co-operative catalysis is not explored yet. In an interesting observation, we have noted that addition of L-proline to PPL catalysed reaction can induce stereoselectivity 15 in the formation of polysubstituted 4H-pyrans while such MCRs catalyzed by PPL alone give only racemic products.

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Section: Resultsmentioning

confidence: 99%

Beyond enzymatic promiscuity: asymmetric induction by l-proline on lipase catalyzed synthesis of polyfunctionalized 4H-pyrans

2015

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“…Synthesis of bioactive and complex molecules should be facile, fast, and efficient with minimal workup in this methodology [17][18][19]. The synthesis of 4H-pyran derivatives has attracted great interest because many of them have useful biological and pharmacological properties, e.g., as anticoagulant, spasmolytic, anticancer, and antianaphylactic agents [20][21][22]. Some 2-amino-4H-pyrans can also be used as photoactive materials [23].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of pyridine-4-carboxylic acid functionalized Fe3O4 nanoparticles as a magnetic catalyst for synthesis of pyrano[3,2-b]pyranone derivatives under solvent-free conditions

Asghari

Mohammadnia

2015

Res Chem Intermed

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Pyridine-4-carboxylic acid (PYCA) functionalized Fe 3 O 4 nanoparticles as an organic-inorganic hybrid heterogeneous catalyst was fabricated and characterized by FT-IR, XRD, TGA, TEM, SEM, and VSM techniques. The catalytic activity of the magnetic catalyst was probed through one-pot synthesis of pyrano[3,2-b]pyranone derivatives from three component reactions of aromatic aldehydes, kojic acid, and ethyl cyanoacetate under solvent-free conditions. Some advantages of this protocol are its environmentally benign method, simple procedure, high yields, and short reaction time. The catalyst was readily separated using an external magnet and reusable without significant loss of its catalytic efficiency.

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“…The synthesis of polyfunctionlized 4H-pyrans group has attracted much attention since it is a constituent of various natural products [20][21][22][23][24][25][26][27][28][29][30]. The 4H-pyran derivatives can be used as anti-coagulants, anticancer agents, anti-anaphylactics, photoactive materials, etc.…”

Section: Introductionmentioning

confidence: 99%

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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The first asymmetric synthesis of polyfunctionalized 4H-pyrans via Michael addition of malononitrile to 2-acyl acrylates

Cited by 22 publications

References 11 publications

Beyond enzymatic promiscuity: asymmetric induction by l-proline on lipase catalyzed synthesis of polyfunctionalized 4H-pyrans

Beyond enzymatic promiscuity: asymmetric induction by l-proline on lipase catalyzed synthesis of polyfunctionalized 4H-pyrans

Synthesis and characterization of pyridine-4-carboxylic acid functionalized Fe3O4 nanoparticles as a magnetic catalyst for synthesis of pyrano[3,2-b]pyranone derivatives under solvent-free conditions

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

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