Imino Diels-Alder Reaction Research Articles

ChemInform Abstract: Synthesis of 1‐(2‐Methyl‐1,2,3,4‐tetrahydroquinolin‐4‐yl)pyrrolidin‐2‐ones from Anilines and N‐Vinyl Pyrrolidin‐2‐one Through Imino Diels—Alder Reaction Using 4‐Nitro Phthalic Acid as Catalyst.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform Abstract: Recent Synthetic Developments in a Powerful Imino Diels—Alder Reaction (Povarov Reaction): Application to the Synthesis of N‐Polyheterocycles and Related Alkaloids.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Solvent-Free Microwave-Assisted Synthesis of New 2-Aryl-Tetrahydroquinolines Using Three-Component Povarov Reaction

A new series of 2-aryl-1,2,3,4-tetrahydroquinolines has been synthesized in good yields through a BiCl3- catalyzed three-component Povarov reaction (imino Diels-Alder cycloaddition) between anilines, benzaldehydes and Nvinylpyrrolidin- 2-one in MeCN. The same series has been prepared without solvent using microwave radiation, which resulted in better yields, a considerable decrease in reaction times and simplified workup. Keywords: 2-Aryl-1,2,3,4-tetrahydroquinolines, microwave-heated three-component Povarov (imino Diels-Alder) reaction, dry media

ChemInform Abstract: Imino Diels—Alder Reactions: Efficient Synthesis of Pyrano and Furanoquinolines Catalyzed by Antimony (III) Sulfate.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

A one-pot synthetic approach to the functionalized isomeric ellipticine derivatives through an imino Diels–Alder reaction

An efficient, three component, one-pot synthesis of new isomeric ellipticine derivatives prepared through an imino Diels–Alder reaction of 3-aminocarbazoles and substituted benzaldehydes with electron-rich alkenes such as 3,4-dihydro-2 H-pyran, 2,3- dihydrofuran and ethyl vinyl ether catalyzed by InCl 3 (10 mol %) in ionic liquid is reported. In the case of substituted benzaldehydes, reductive amination is observed.

Synthesis of 1-(2-Methyl-1,2,3,4-tetrahydroquinolin-4-yl) pyrrolidin-2-ones from Anilines and N-Vinyl Pyrrolidin-2-one Through Imino Diels–Alder Reaction Using 4-Nitro Phthalic Acid as Catalyst

Aryl amines react smoothly and efficiently with N-vinyl pyrrolidin-2-one in the presence of 4-nitro phthalic acid in acetonitrile to afford the corresponding 1-(2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)pyrrolidin-2-ones in good yields.

Imino Diels-Alder Reactions: Efficient Synthesis of Pyrano and Furanoquinolines Catalyzed by Antimony (III) Sulfate

The Imino Diels-Alder reaction of N-benzylideneanilines with 3, 4-dihydro-2H-pyran and 2, 3-dihydrofuran proceeds smoothly to afford pyrano and furanoquinolines 3a-i and 4a-i in the presence of Antimony (III) Sulfate as catalyst. A concise and efficient synthetic route has been developed for one pot synthesis of pyrano and furano quinolines 6a-l and 7a-l by the reaction between anilines and 3, 4-dihydro-2H- pyran and 2, 3-dihydrofuran respectively in fairly good yields. This catalyst is inexpensive, easily available and it was also found that catalyst could be recovered quantitatively and reused without much loss of catalytic activity. Keywords: Antimony (III) sulfate, imino diels-alder reactions, 3,4-dihydro-2H-pyran, 2,3- dihydrofuran, aryl amines, tetrahydroquinolines

A novel heterotricyclic assembly through intramolecular imino Diels–Alder reaction: synthesis of pyrrolo[3,4- b]quinolines

The synthesis of a series of hexahydropyrrolo[3,4- b]quinolines has been achieved in excellent yields by the reaction of aldimines derived from aromatic amines and N-prenylated aliphatic aldehydes in acetonitrile with InCl 3 as a catalyst in a short duration of time.

ChemInform Abstract: Lewis Acid Promoted Imino Diels—Alder Reactions of 5‐Dienyl Pyrimidinones with N‐Aryl/Naphthyl Imines: Synthesis of Novel Quinoline/Benzoquinoline Derivatives.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

In vitro antifungal activity of polyfunctionalized 2-(hetero)arylquinolines prepared through imino Diels–Alder reactions

Diverse polyfunctionalized quinolines, easily prepared using Lewis acid-catalyzed imino Diels–Alder reactions between corresponding aldimines, were tested for antifungal properties against standardized as well as clinical isolates of clinically important fungi. Among them, 4-pyridyl derivatives displayed the best activities mainly against dermatophytes. The activity appears not to be related neither to the lipophilicity nor to the basicity of compounds.

An Efficient, One-Pot Synthesis of Isomeric Ellipticine Derivatives through Intramolecular Imino-Diels−Alder Reaction

New analogues of isomeric ellipticine derivatives fused with biologically important pyrroloindole or chromene moiety have been synthesized by utilizing an intramolecular imino Diels-Alder reaction in a single step.

ChemInform Abstract: Imino Diels—Alder Reactions: Efficient Synthesis of Pyrano‐ and Furanoquinolines Catalyzed by 4‐Nitrophthalic Acid.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform Abstract: Three‐Component Imino Diels—Alder Reaction with Essential Oil and Seeds of Anise: Generation of New Tetrahydroquinolines.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

New Findings on the Cerium(IV) Ammonium Nitrate Catalyzed Povarov Reaction: Stereoselective Synthesis of 4-Alkoxy-2-aryl-1,2,3,4-tetrahydro­quinoline Derivatives

Cerium(IV) ammonium nitrate catalyzes the three-com- ponent, imino Diels-Alder (Povarov) reaction between anilines, ar- omatic aldehydes, and acyclic vinyl ethers, giving cis-4-alkoxy-2- aryl-1,2,3,4-tetrahydroquinolines with almost complete diastereo- selectivity. The corresponding reaction starting from cyclic vinyl ethers gave the two possible diastereomers, with the endo-com- pound as the major product. This stereochemical outcome is ex- plained through a stepwise mechanism for the imino Diels-Alder reaction, and this mechanism was subsequently proved by trapping the putative oxonium intermediate in the presence of ethanol.

Indium chloride/silica gel supported synthesis of pyrano/thiopyranoquinolines through intramolecular imino Diels–Alder reaction using microwave irradiation

A facile synthesis of pyrano/thiopyranoquinolines is accomplished in excellent yields through imino Diels–Alder reaction using silica gel impregnated with indium trichloride as catalyst.

Indium Trichloride Catalysed Imino Diels-Alder Reaction of Imesatins: A Facile Synthesis of Novel Spirooxindole 1H – pyrano[2,3-c ]quinolines

A novel method for the construction of spirooxindole via imino Diels-Alder reaction of in situ generated isatin imine with dihydropyran is reported. InCl3 efficiently catalyzes the reaction to afford cis- and trans-diastereisomers in fairly good yields. Keywords: Indium chloride, imino Diels-Alder reaction, isatin, tetrahydroquinoline, spirooxindole

Imino Diels-Alder Reactions: Efficient Synthesis of 2-Aryl-4-(2′-oxopyrrolidinyl-1′)-1,2,3,4-tetrahydroquinolines catalyzed by Antimony(III) Sulfate

Antimony(III) sulfate is found to catalyze the imino Diels-Alder reaction of Schiff’s bases with N-vinylpyrrolidin-2-one to afford 2-aryl-4-(2′-oxopyrrolidinyl-1′)-1,2,3,4-tetrahydroquinolines. One-pot synthesis of 1,2,3,4-tetrahydroquinolines from 3-nitro benzaldehyde and aromatic amines with N-vinylpyrrolidin-2-one catalyzed by antimony(III) sulfate is also reported. This catalyst is inexpensive, easily available, and it was also found that catalyst could be recovered quantitatively and reused without much loss of catalytic activity.

Lewis acid promoted imino Diels–Alder reactions of 5-dienyl pyrimidinones with N-aryl/naphthyl imines: synthesis of novel quinoline/benzoquinoline derivatives

The chemo- as well as regioselective imino Diels–Alder reactions of 5-dienyl pyrimidinones with N-aryl as well as N-naphthyl imines in the presence of a different Lewis acid catalysts resulting in novel quinoline and benzoquinoline derivatives are reported.

Imino Diels-Alder Reactions: Efficient Synthesis of Pyrano- and Furanoquinolines Catalyzed by 4-Nitrophthalic Acid

4-Nitrophthalic acid was found to be an effective catalyst for the imino Diels-Alder reaction of N-benzylideneanilines with 3,4-dihydro-2H-pyran and 2,3-dihydrofuran to afford pyrano- and furanoquinolines in good yields. It was also found that aryl amines react smoothly with 3,4-dihydro-2H-pyran and 2,3-dihydrofuran under the same condition to afford the corresponding pyrano- and furanoquinolines in high yields. This catalyst is inexpensive, easily available, water soluble, and stable to aqueous reaction conditions.

Three-component imino Diels–Alder reaction with essential oil and seeds of anise: generation of new tetrahydroquinolines

A simple and efficient one-pot method for the synthesis of 4-anisyl-2-phenyl-1,2,3,4-tetrahydroquinoline derivatives using a three-component imino Diels–Alder cycloaddition (Povarov reaction) between anilines, benzaldehyde, and trans-anethole in the presence of acidic catalysts is shown. New substituted tetrahydroquinolines are reported and their direct preparation from the anise essential oil is described. Also, a simple procedure of the same tetrahydroquinolines from the anise seeds under supercritical fluid (CO 2) conditions has been reported.