Heterodiene cycloadditions of benzopyran derivatives.

Cover of: Heterodiene cycloadditions of benzopyran derivatives. | Ian Wardell

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PhD thesis, Chemistry and Applied Chemistry.

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Open LibraryOL21683950M

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Buy Synthetic Transformations of Conjugated Heterodienes: Heterodiene cycloadditions on FREE SHIPPING on qualified orders. Heterodiene cycloadditions of benzopyran derivatives. Author: Wardell, Ian. ISNI: Awarding Body: University of Salford Current Institution: University of Salford Date of Award: Availability of Full Text: Access from EThOS.

Heterodiene cycloadditions of 4-oxo-4Hbenzopyrans with formyl, acetyl, or carboxyl substituents at C-3 to 1-alkoxy- or 1,1-dialkoxyalkenes produce 3-alkoxy- or 3,3-dialkoxy-4,4a- dihydropyrano[4,3-b][1]benzopyranones which are capable of a variety of selective transformations, including acid-induced epimerisation and/or retro-cycloaddition, reduction, Cited by: Heterodiene cycloadditions of 3-formylchromone 2 to a series of ketene acetals 1 derived from C 2 symmetric 1,2-diarylethane-1,2-diols are diastereoselective.

From (S,S)-1,2-di(o-tolyl)ethane-1,2-diol 6c the major cycloadduct 3c was isolated by crystallisation and transformed by acid-catalysed methanolysis into (S)-methyl 4-oxo-3,4-dihydro-2Hbenzopyranylacetate 5, Cited by: Benzopyran Derivative.

4Hbenzopyranone,3,5,7-trihydroxyphenyl or 3,5,7-trihydroxyflavone, is a polyphenolic compound derived primarily from different medicinal herbs. Further development of simple γ-pyrones as the 2π-component in 1,3-dipolar cycloadditions of stabilized and nonstabilized azomethine ylides has provided some.

Heterodiene cycloadditions of 4-oxo-4Hbenzopyrans with formyl, acetyl, or carboxyl substituents at C-3 to 1-alkoxy- or 1,1-dialkoxyalkenes produce 3-alkoxy- or 3,3-dialkoxy-4,4a- dihydropyrano. Nevertheless, the benzopyran nucleus is frequently observed in other phenolic compounds from Hypericum species, such as acylphloroglucinol derivatives, benzophenones, and xanthones.

This nucleus is formed by the cyclization of a prenyl radical with a vicinal aromatic hydroxyl group, substituents commonly occurring in these substances. Chromonecarboxylic acid 1 undergoes heterodiene cycloadditions to alkoxyalkenes 2, producing novel pyrans which on treatment with alkanols or water decompose into functionalised 1,5-dicarbonyl systems 6 – 11, the sequence being potentially general for 2-acylenoic acids.

Heterodiene synthesis. Part XVII. Reactions of 2-oxoindolinylidene derivatives with enamines: a Michael pathway as an alternative to 1,2- and 1,4-cycloadditions.

Gianfranco Tacconi, Anna Gamba Invernizzi and Giovanni Desimoni Abstract. The reactions of enamines with 2-oxoindolinylidene-acetates and -acetophenones have been studied. Challand's 18 research works with citations and reads, including: ChemInform Abstract: Synthesis of Carbocyclic Nucleosides.

The stereodivergent asymmetric hetero‐Diels‐Alder reaction of achiral and chiral 1‐oxa‐1,3‐butadienes carrying an oxazolidine moiety with various enol ethers in the presence of different Lewis acids is described as a highly stereoselective and efficient approach to dihydropyrans, which can be used for the synthesis of carbohydrates.

The effect of substituents on the site selectivity (CC vs CN) in the [4 + 2] cycloaddition between heterocumulenes (ketene imines) 2a−g with heterodienes (acroleines 9a−n and 4-acylfuran-2,3-diones 1a−d) is treated by semiempirical AM1 molecular orbital and density functional calculations using Becke's three-parameter hybrid method (B3LYP/G*).

Benzopyran and benzodihydropyran (chromane) nuclei are the core structure of many natural products, in particular flavonoids. Many compounds possessing this structure are nutraceuticals, pharmaceutical nutrients. Therefore, benzopyran and chromane scaffolds are important building blocks in organic synthesis and many efforts have been made to set up efficient methods for.

Peter J. Cremins, Suthiweth T. Saengchantara, Timothy W. Wallace, Cycloadditions of substituted benzopyranones to electron-rich dienes: a new route to xanthone derivatives, Tetrahedron, /S(01), 43, 13, (), (). This review is focused on the enantioselective synthesis of 3,4-dihydropyran derivatives, whose importance as chiral building blocks in the synthesis of bioactive molecules and natural products is well established.

The review analyzes the different synthetic strategies by grouping them as a function of the atom numbers of the reagents involved. Starting from the. This paper reviews the use of solid-phase parallel synthesis in the construction of 2 H-benzopyran libraries that contain substituted 2 H-benzopyrans (A, B, and C) and additional cycle-fused benzopyrans (D and E), except the derivatives of 1 H-benzopyran, coumarin, and chromone moieties ().In addition, the solid-phase synthesis of modified benzopyran derivatives using the 2 H-benzopyran.

Heterodiene [4pi+2pi] cycloadditions of (S,S)-4,5-diarylmethylene-1,3-dioxolanes 1 to a series of beta-amido-alpha,beta-unsaturated carbonyl compounds are diastereoselective (r than. The chemo- regio- and stereoselectivities of multicomponent [4 + 2]/[3 + 2] domino cycloaddition reactions involving nitroindole derivatives with vinylethers and acrylates are studied computationnally and compared to experimental results.

In this process, the nitroarene first reacts as an electron-deficient heterodiene with the electron-rich alkene following an. The cycloadditions do not require the use of catalysts and are highly endo diastereoselective, and in water the cyclic nitrona 18, and 23 are converted into chromene derivatives via.

Heterodiene cycloadditions of 3-formyl chromone to ketene acetals derived from C-symmetric 1,2-diarylethane-1,2-diols are diastereoselective; methanolysis of the cycloadducts derived from (,)-hydrobenzoin releases optically enriched methyl 3,4-dihydrooxobenzopyranylacetate and the optically pure 1,2-diol.

Synthesis and structural analysis of (E)(2′-nitrovinyl)indoles from the corresponding 2-formylindole derivatives. Journal of Heterocyclic Chemistry37 (5), Reactions of the azoalkenes (E,E)methyl-N-phenyl-2,3-diazapenta-2,4-dienecarboxamide 2 and methyl (E,Z)methylphenylcarbamoyl-1,2-diazabuta-1,3-dienecarboxylate 3, having respectively an electron-rich and an electron-poor group on nitrogen, are nd 2, is a stable compound and its stereochemistry was established as E,Eby X-ray crystallography.

This review presents a survey of the condensations of 3-formylchromone with various active methylene and methyl compounds, e.g. malonic or barbituric acid derivatives, five-membered heterocycles, etc.

The utilisation of the condensation products for the synthesis of different heterocyclic systems, which is based on the ability of the γ-pyrone ring to be opened by the. The 1-methylquinolone (MeQone) framework is often found in alkaloids and recently attention was drawn to unnatural MeQone derivatives with the aim of finding new biologically active compounds, however, low reactivity of the MeQone framework prevents the syntheses of versatile derivatives.

A nitro group is one of the useful activating groups for this framework that. The scope of the reaction was next evaluated with respect to a series of substituted 1,2-diazine derivatives.

For instance, benzo[g]phthalazine 12 provided the expected product 13 in good yield, with high diastereoselection (d.r. >Table 1, Entry 5).The reaction of alkyne 2 with 6,7-dimethyl phthalazine 14 gave lactam 15 in 65% yield and.

Van Broeck PI, Van Doren PE, et al () Diels–Alder reactions of pyrano[3,4-b]indolones and a 2-benzopyranone with hetero substituted olefins: generation of carbazole and naphthalene derivatives by elimination instead of dehydrogenation. J Chem Soc, Perkin Trans 1 – Google Scholar. Background: In recent decades, natural products are an important source of chemotherapeutics as more than half of the effective cancer drugs can b.

Perspective. D.L. Boger, The difference a single atom can make: synthesis and design at the chemistry-biology interface, J. Org. Chem.82, Azadiene Diels-Alder Reactions: Scope and Applications.

The inverse-electron-demand HDA reactions between cycloalkylidene derivatives 17 or 20 and cyclic enol ether 22 were performed in toluene solution at °C for 24 h and the dispiropyrans 23 and 24 were obtained in good (87–93 %) yields.

For all cycloadditions, high diastereoselectivity was observed. A novel synthesis of triazolo[1,2-a]indazole-1,3,8-trione derivatives by reaction of urazole, dimedone and aromatic aldehydes under conventional heating and microwave irradiation and solvent-free conditions using silica nanoparticles prepared from rice husk ash as catalyst is described.

The new method features high yields, multicomponent reactions and environmental. A series of pyrano[4,3-b][1]benzopyranones (7a–t) were synthesized through hetero-Diels-Alder reaction of substituted 3-formylchromones (5) with enol ethers (6), characterized by IR, 1 H NMR, 13 C NMR, and mass spectral techniques.

All the compounds were evaluated for antimicrobial activity against various bacterial and fungal strains, found to possess significant. Chiral nonracemic aminated nitroso acetals were synthesized via diastereoselective multicomponent [4 + 2]/[3 + 2] cycloadditions employing new (S,E)-γ-nitrogenated nitroalkenes 5a–c as heterodienes, ethyl vinyl ether (EVE) as a dienophile, and selected electron-deficient alkenes as 1, employment of different organic solutions of LiClO 4 or LiCl.

Cycloaddition reactions, in general, are one of the most powerful and frequently applied methods for the construction of cyclic frameworks. 1 In general, [m+n] cycloadditions can be induced by heat, light, Lewis acids, high pressure, and sonication.

1 The [2+2] cycloaddition is a thermally forbidden process as predicted by the Woodward–Hoffmann rules, 2 but it can be achieved. An ortho-quinone methide (o-QM) is a highly reactive chemical motif harnessed by nature for a variety of its extraordinary reactivity and biological importance, it is surprising how few applications within organic synthesis exist.

We speculate that their widespread use has been slowed by the complications that surround the preparation of their precursors. Uncatalyzed [4 + 2] Cycloadditions of 3-Nitrocoumarins with Vinyl Ethers in Solventless Conditions.

A New Entry to Chromene Derivatives David Amantini, Francesco Fringuelli, and Ferdinando Pizzo. Condensations of 1 with malonic acid derivatives.

3-Formylchromones readily react with malonic acid and its derivatives in the presence of base, mostly pyridine ().Reaction of 1 with malonic acid [8,9] or diethyl malonate [9,10] in the presence of pyridine afforded E-β-(4-oxo-4Hbenzopyranyl)acrylic acids 2a (R 1 = H) or ethyl acrylates 2b (R 1 = C 2 H 5), which.

Enaminones in the synthesis of heterocyclic systems. [2+2] Cycloadditions, ring expansion reactions and other transformations; Design, synthesis and pharmacological properties of new thiazole and thiadiazole derivatives; Cultivating over thirty years the passion to build heterocycles from 1,2-diaza-1,3-dienes.

ChemInform Abstract: 1,4‐Remote Stereocontrol by Asymmetric Catalytic Carbonyl‐Ene Reaction with Chiral Homoallylic Ethers: An Application to the Asymmetric Synthesis of (11R,14S)‐anti‐ and (31R,34S)‐syn‐Segments of Immunosuppressant Rapamycin.

Saturated heterocycles. Application of the seth‐paul‐van duyse equation. The C O stretching frequencies and transmission of substituent effects in 5,6‐polymethylene‐2,3,5,6‐tetrahydro‐1,3‐oxazin‐4‐one derivatives. An efficient synthesis of 2,4,5-triaryl-1H-imidazole derivatives catalyzed by boric acid in aqueous media under ultrasound-irradiation.

Bull. Korean Chem. Soc.,30 (5). OrganicReactions VOLUME EDITORIAL BOARD Evans,Editor-in-Chief b,Executive Editor JeffreyAubé er itz AlbertPadwa ore ker.INTRODUCTION:Triazoles are the class of heterocyclic compounds 1 which are under study since many a years.

1, 2, 4-Triazole is one of a pair of isomeric chemical compounds with molecular formula C 2 H 3 N 3, called triazoles, which have a five-membered ring of two carbon atoms and three nitrogen atoms azole ring are readily able to bind with a variety of enzymes .Journal list menu.

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