MICROWAVE ASSISTED SYNTHESIS OF 4,6-DIARYLPYRIDAZIN-3(2<i>H</i>)-ONES IN SOLID STATE

Meenakshi, C.; Ramamoorthy, V.; Muthusubramanian, Shanmugam; Sivasubramanian, S.

doi:10.1081/scc-100103250

Cited by 12 publications

(3 citation statements)

References 9 publications

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“…In one of the steps of the synthesis of antimicrobial pyrimidine-5-carboxylates, the 3,4-dihydropyrimidine ring was aromatized to a pyrimidine ring using SeO 2 [83]. Microwave-assisted dehydrogenation of 4,6-diaryl-4,5-dihydropyridazin-3(2 H )-ones to 4,6-diarylpyridazin-3(2 H )-ones, with SeO 2 in the solid state is a good way for the aromatization of the heterocyclic ring because of the short reaction times and high yields of products (79%–84%) [84].…”

Section: Selenium(iv) Oxide and Selenic(iv) Acid As Oxidizing Agenmentioning

confidence: 99%

Developments in Synthetic Application of Selenium(IV) Oxide and Organoselenium Compounds as Oxygen Donors and Oxygen-Transfer Agents

2015

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A variety of selenium compounds were proven to be useful reagents and catalysts for organic synthesis over the past several decades. The most interesting aspect, which emerged in recent years, concerns application of hydroperoxide/selenium(IV) oxide and hydroperoxide/organoselenium catalyst systems, as "green reagents" for the oxidation of different organic functional groups. The topic of oxidations catalyzed by organoselenium derivatives has rapidly expanded in the last fifteen years This paper is devoted to the synthetic applications of the oxidation reactions mediated by selenium compounds such as selenium(IV) oxide, areneseleninic acids, their anhydrides, selenides, diselenides, benzisoselenazol-3(2H)-ones and other less often used other organoselenium compounds. All these compounds have been successfully applied for various oxidations useful in practical organic syntheses such as epoxidation, 1,2-dihydroxylation, and α-oxyfunctionalization of alkenes, as well as for ring contraction of cycloalkanones, conversion of halomethyl, hydroxymethyl or active methylene groups into formyl groups, oxidation of carbonyl compounds into carboxylic acids and/or lactones, sulfides into sulfoxides, and secondary amines into nitrones and regeneration of parent carbonyl compounds from their azomethine derivatives. Other reactions such as dehydrogenation and aromatization, active carbon-carbon bond cleavage, oxidative amidation, bromolactonization and oxidation of bromide for subsequent reactions with alkenes are also successfully mediated by selenium (IV) oxide or organoselenium compounds. The oxidation mechanisms of ionic or free radical character depending on the substrate and oxidant are discussed. Coverage of the literature up to early OPEN ACCESSMolecules 2015, 20 10206 2015 is provided. Links have been made to reviews that summarize earlier literature and to the methods of preparation of organoselenium reagents and catalysts.

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Section: Selenium(iv) Oxide and Selenic(iv) Acid As Oxidizing Agenmentioning

confidence: 99%

Developments in Synthetic Application of Selenium(IV) Oxide and Organoselenium Compounds as Oxygen Donors and Oxygen-Transfer Agents

2015

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“…It is important to note that the reaction did not effectively take place without silica gel supported zeolite-HY [395]. Interestingly, when a γ-ketoacid and hydrazine hydrate were reacted under microwave irradiation, the unsubstituted N-dihydropyridazinone was obtained directly in one-step in good yield [396].…”

Section: Pyridazine Derivativesmentioning

confidence: 98%

Recent Advances in Microwave-Assisted Synthesis of Heterocyclic Compounds

Molteni¹,

Ellis²

2005

COS

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“…Heating of equimolar amounts of the reactants in boiling acetic acid led to the formation of pyridazine derivative IV in which the dimedone fragment remained unchanged (Scheme 3). The synthesis of simpler pyridazinones from γ-keto acids is well known [8]. As nitrogen-containing binucleophiles we also used o-and p-phenylenediamines.…”

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Reactions of dimedone-β-benzoylacrylic acid adduct with nitrogen-containing binucleophiles

Vatolina¹,

Andin²

2011

Russ J Org Chem

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2-(2-Hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)-4-oxo-4-phenylbutanoic acid (dimedone adduct with β-benzoylacrylic acid) reacted with ethylenediamine and benzidine to give bis-quinoline derivatives. In the reaction with tryptamine a product containing hexahydroquinoline and indole fragments was obtained, while the reaction with phenylhydrazine hydrochloride afforded pyridazine derivative. The reactions with o-and p-phenylenediamines involved retro-Michael decomposition of the initial adduct and formation of enamino derivatives of dimedone. X = CH 2 CH 2 (a), p-C 6 H 4 C 6 H 4 -p′ (b).Polycarbonyl compounds derived from cyclic 1,3-diketones and electron-deficient 1,2-disubstituted ethylenes possess 1,3-, 1,4-, or 1,5-dicarbonyl fragment and are convenient model structures for various heterocyclizations, e.g., in reactions with nitrogencentered nucleophiles. These reactions could lead to the formation of heterocyclic compounds belonging to the pyrrole, quinoline, pyrroloquinoline, and pyridazine series, and they attract much interest from the viewpoint of molecular design. Some products obtained as a result of the above heterocyclization are important as potential physiologically active substances. For example, data on the use of tetra-and hexahydroquinoline derivatives as analgesic, antiallergic, antiphlogistic, and antipyretic agents have been reported [1-3].It was shown previously that 2-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)-4-oxo-4-phenylbutanoic acid (I, Michael adduct of dimedone and β-benzoylacrylic acid) reacts with ammonia to give pyrrolo-[4,3,2-de]quinoline derivative [4] and that hexahydroquinoline derivatives are formed in reactions of I with primary amines [5]. N-Heterocyclizations of other polycarbonyl compounds, products of Michael addition of dimedone to 1,2-dibenzoylethylene [6] and 1,1-diacetyl-2-benzoylethylene [7], were also studied, and the resulting nitrogen-containing heterocycles were identified as pyrrole, quinoline, and pyrrolo-[3,4-c]quinoline derivatives.In the present work we examined reactions of adduct I with some nitrogen-centered binucleophiles, in particular ethylenediamine, benzidine, phenylhydrazine hydrochloride, o-and p-phenylenediamines, and a biogenic amine, tryptamine, with a view to determine their regioselectivity. The reactions with ethylenediamine and benzidine were carried out by heating the reactants in boiling acetic acid; the substrate-diamine molar ratio was 1 : 1.5 for ethylenediamine and 2 : 1 for benzidine. As a result, we obtained the corresponding bis-quinoline derivatives IIa and IIb (Scheme 1);

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MICROWAVE ASSISTED SYNTHESIS OF 4,6-DIARYLPYRIDAZIN-3(2H)-ONES IN SOLID STATE

Cited by 12 publications

References 9 publications

Developments in Synthetic Application of Selenium(IV) Oxide and Organoselenium Compounds as Oxygen Donors and Oxygen-Transfer Agents

Developments in Synthetic Application of Selenium(IV) Oxide and Organoselenium Compounds as Oxygen Donors and Oxygen-Transfer Agents

Recent Advances in Microwave-Assisted Synthesis of Heterocyclic Compounds

Reactions of dimedone-β-benzoylacrylic acid adduct with nitrogen-containing binucleophiles

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