Intramolecular Imino Diels-Alder Reaction Research Articles

Brønsted and Lewis Solid Acid Catalysts in the Valorization of Citronellal

Terpenes are valuable starting materials for the synthesis of molecules that are of interest to the flavor, fragrance, and pharmaceutical industries. However, most processes involve the use of mineral acids or homogeneous Lewis acid catalysts. Here, we report results obtained in the liquid-phase reaction of citronellal with anilines under heterogeneous catalysis conditions to give tricyclic compounds with interesting pharmacological activity. The terpenic aldehyde could be converted into octahydroacridines with a 92% yield through an intramolecular imino Diels–Alder reaction of the imine initially formed in the presence of an acidic clay such as Montmorillonite KSF. Selectivity to the desired product strongly depended on the acid sites distribution, with Brønsted acids favoring selectivity to octahydroacridine and formation of the cis isomer. Pure Lewis acids such as silica–alumina with a very low amount of alumina gave excellent results with electron-rich anilines like toluidine and p-anisidine. This protocol can be applied starting directly from essential oils such as kaffir lime oil, which has a high citronellal content.

Highly stereoselective and catalyst-free synthesis of annulated tetrahydropyridines by intramolecular imino-Diels–Alder reaction under microwave irradiation in water

Highly stereoselective intramolecular imino-Diels–Alder reaction without any catalyst in water and under microwave irradiation for the synthesis of complex organic systems.

Synthesis and antibacterial property of pyrrolopyrano quinolinones and pyrroloquinolines

Synthesis of a series of novel pyrroloquinolinone and pyrroloquinoline derivatives has been accomplished by intramolecular domino Knoevenagel hetero Diels–Alder reaction and intramolecular imino Diels–Alder reaction. These compounds were evaluated for their antibacterial activity against bacterial pathogens using disc diffusion and broth dilution methods. The efficacy of binding of these compounds to gyrase, an enzyme known to play a key role in bacterial replication is examined by studying its supercoiling and relaxation and also its gene expression using PCR method. The results indicated that most of the synthesised compounds exhibited good antibacterial activity against the microorganisms with MIC values of 5mM and could inhibit gyrase effectively leading to cell death.

Intramolecular Imino Diels−Alder Reaction: Progress toward the Synthesis of Uncialamycin

We herein described an intramolecular imino Diels-Alder reaction promoted with BF(3).OEt(2)/DDQ affording substituted quinolines. Using this procedure, we prepared the chiral quinoline moiety of the uncialamycin, a new enediyne natural product.

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.

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.

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.

Highly diastereoselective synthesis of new indolopyrroloquinolines through intramolecular imino Diels–Alder reactions

A new, efficient and highly diastereoselective one-pot synthesis of cis-fused indolopyrroloquinoline derivatives is described through imino Diels–Alder reaction of substituted anilines or naphthylamines with N-prenylated-2-formyl-3-chloroindoles catalyzed by La(OTf) 3.

A Rapid Intramolecular Imino Diels-Alder Reaction of Aminoanthraquinones with Citronellal or Prenylated Salicylaldehydes: Substituent Effect on Changing the Reaction Pathway from Diels-Alder to Ene-Type Cyclization

The reaction of 1-aminoanthraquinone with citronellal or substituted prenylated salicylaldehyde catalyzed by triphenylphosphonium perchlorate (TPPP) is reported. The nature of the substituents in salicylaldehyde changes the reaction pathway from Diels-Alder to ene-type cyclization.

Indium trichloride catalyzed one-pot synthesis of indolo[2,1- a]pyrrolo[4′,3′:2,3]-7a,8,13,13b-tetrahydroquinolines through intramolecular imino Diels–Alder reactions

An efficient synthesis of tetrahydroquinolines has been achieved by the reaction of aldimines derived from various substituted aromatic amines and indole-2-carbaldehyde containing an internal dienophile using 20 mol % InCl 3 in acetonitrile at room temperature. The reactions are very fast and the products are isolated in good yields and in pure form.

Intramolecular imino-Diels–Alder reactions in [bmim]BF 4 ionic medium: Green protocol for the synthesis of tetrahydrochromanoquinolines

2-Azadienes derived in situ from aryl amines and O-prenyl derivatives of salicylaldehydes under intramolecular [4 + 2] imino-Diels–Alder reaction, in an air and moisture stable [bmim]BF 4 ionic medium afford tetrahydrochromanoquinolines in high to quantitative yield. This new protocol offers significant advantages over reported methods which include mild reaction conditions, high conversions, enhanced reaction rates and recyclability of ionic liquids.

InCl3 as an efficient catalyst for intramolecular imino Diels–Alder reactions: Synthesis of tetrahydrochromano quinolines

InCl3 is found to be an efficient catalyst for the Intramolecular Imino Diels-Alder (IMIDA) reaction of aldimines derived from aromatic amines and O-allyl derivatives of salicylaldehydes to afford the corresponding tetrahydrochromano(4,3-b)quinolines in excellent yields under mild conditions and short reaction times.

Inter‐ and Intramolecular Imino Diels—Alder Reactions Catalyzed by Sulfamic Acid: A Mild and Efficient Catalyst for a One‐Pot Synthesis of Tetrahydroquinolines.

The successful use of sulfamic acid as a catalyst in the inter- and intramolecular Inverse Electron Demand Diels-Alder reactions of iminodienes is described. A one-pot synthesis of tetrahydroquinolines was achieved by three component coupling of benzaldehyde and anilines with electron-rich dienophiles such as 2,3-dihydrofuran, dihydropyran and cyclopentadiene catalyzed by sulfamic acid (H 2 NSO 3 H). The intramolecular cycloaddition of imines, derived from O-prenylsalicylaldehyde with anilines catalyzed by sulfamic acid proceeds smoothly and yielded the diastereomeric tetrahydrochromanoquinolines in good yields.

Inter- and Intramolecular Imino Diels-Alder Reactions Catalyzed by Sulfamic Acid: A Mild and Efficient Catalyst for a One-Pot Synthesis of Tetrahydroquinolines

The successful use of sulfamic acid as a catalyst in the inter- and intramolecular Inverse Electron Demand Diels-Alder reactions of iminodienes is described. A one-pot synthesis of tetrahydroquinolines was achieved by three component coupling of benzaldehyde and anilines with electron-rich dienophiles such as 2,3-dihydrofuran, dihydropyran and cyclopentadiene catalyzed by sulfamic acid (H 2 NSO 3 H). The intramolecular cycloaddition of imines, derived from O-prenylsalicylaldehyde with anilines catalyzed by sulfamic acid proceeds smoothly and yielded the diastereomeric tetrahydrochromanoquinolines in good yields.

The type 2 intramolecular imino Diels-Alder reaction. Synthesis and structural characterization of bicyclo[n.3.1] bridgehead olefin/bridgehead lactams

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTThe type 2 intramolecular imino Diels-Alder reaction. Synthesis and structural characterization of bicyclo[n.3.1] bridgehead olefin/bridgehead lactamsTimothy G. Lease and K. J. SheaCite this: J. Am. Chem. Soc. 1993, 115, 6, 2248–2260Publication Date (Print):March 1, 1993Publication History Published online1 May 2002Published inissue 1 March 1993https://doi.org/10.1021/ja00059a022RIGHTS & PERMISSIONSArticle Views543Altmetric-Citations73LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (2 MB) Get e-AlertsSupporting Info (2)»Supporting Information Supporting Information Get e-Alerts

Alkaloid synthesis by the intramolecular imino Diels-Alder reaction. .delta.-Coniceine and tylophorine

Alkaloid synthesis by the intramolecular imino Diels-Alder reaction. .delta.-Coniceine and tylophorine