Step-Controlled Povarov-Type Reaction with 1,2-Dihydroquinolines as Precursors of Dienophiles: Direct Synthesis of Spirocyclic Bi-tetrahydroquinolines and Functionalized 1,2-Dihydroquinolines.

A novel Povarov-type reaction for straightforward synthesis of novel spiro bi-tetrahydroquinolines with readily available 1,2-DHQs (1,2-dihydroquinolines) and aromatic imines was developed. The reaction could be selectively stopped at the first stage under a Brønsted acid catalyst to afford the corresponding functionalized 1,2-DHQs conveniently.

• Publication year

  2017

• Venue

  Organic Letters

• Publication date

  2017-01-06

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1021/acs.orglett.6b03330PMID 27934062
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

• Catalytic Enantioselective Synthesis of Tetrahydroquinolines Containing All-carbon Quaternary Stereocenters via Formation of Aza-ortho-xylylene with 1,2-Dihydroquinoline as Precursor

  2015cited by this paper
• Sodium salts of anionic chiral cobalt(III) complexes as catalysts of the enantioselective Povarov reaction.

  2015cited by this paper
• Enantioselective Organocatalytic Transfer Hydrogenation of 1,2-Dihydroquinoline through Formation of Aza-o-xylylene.

  2015cited by this paper
• Oxidative Povarov reaction via sp³ C-H oxidation of N-benzylanilines induced by catalytic radical cation salt: synthesis of 2,4-diarylquinoline derivatives.

  2015cited by this paper
• Three-component Povarov reaction-heteroannulation with arynes: synthesis of 5,6-dihydroindolo[1,2-a]quinolines.

  2014cited by this paper
• Dual C–H Functionalization of N-Aryl Amines: Synthesis of Polycyclic Amines via an Oxidative Povarov Approach

  2014cited by this paper
• Povarov-type reaction using methyl as new input: direct synthesis of substituted quinolines by I2-mediated formal [3 + 2 + 1] cycloaddition.

  2014cited by this paper
• Chiral Phosphoric Acid‐Catalyzed Enantioselective Three‐ Component Aza‐Diels–Alder Reactions of Aminopyrroles and Aminopyrazoles

  2014cited by this paper
• Understanding the mechanism of the Povarov reaction. A DFT study

  2014cited by this paper
• A catalytic asymmetric isatin-involved Povarov reaction: diastereo- and enantioselective construction of spiro[indolin-3,2'-quinoline] scaffold.

  2013cited by this paper
• Conjugate-base-stabilized Brønsted acids as asymmetric catalysts: enantioselective Povarov reactions with secondary aromatic amines.

  2013cited by this paper
• Catalytic highly enantioselective vinylogous Povarov reaction.

  2013cited by this paper
• Identification of N-substituted 8-azatetrahydroquinolone derivatives as selective and orally active M(1) and M(4) muscarinic acetylcholine receptors agonists.

  2013cited by this paper
• Highly enantioselective three-component Povarov reaction catalyzed by SPINOL-phosphoric acids

  2013cited by this paper
• A hetero Diels-Alder approach to the synthesis of chromans (3,4-dihydrobenzopyrans) using oxonium ion chemistry: the oxa-Povarov reaction.

  2013cited by this paper
• Design and synthesis of potent antagonists containing rigid spirocyclic privileged structures for the CGRP receptor.

  2012cited by this paper
• An asymmetric organocatalytic Povarov reaction with 2-hydroxystyrenes.

  2012cited by this paper
• Enantioselective methodologies for the synthesis of spiro compounds.

  2012cited by this paper
• Chiral phosphoric acid-catalyzed enantioselective three-component Povarov reaction using enecarbamates as dienophiles: highly diastereo- and enantioselective synthesis of substituted 4-aminotetrahydroquinolines.

  2011cited by this paper
• Asymmetric synthesis of tetrahydroquinolines with quaternary stereocenters through the Povarov reaction.

  2011cited by this paper
• TEMPO oxoammonium salt-mediated dehydrogenative Povarov/oxidation tandem reaction of N-alkyl anilines.

  2011cited by this paper
• Spiroindolones, a Potent Compound Class for the Treatment of Malaria

  2010cited by this paper
• Unsaturated lactams: new inputs for povarov-type multicomponent reactions.

  2010cited by this paper
• Asymmetric three-component inverse electron-demand aza-Diels-Alder reaction: efficient synthesis of ring-fused tetrahydroquinolines.

  2010cited by this paper
• 4-Hydroxy-3-methoxyphenyl Substituted 3-methyl-tetrahydroquinoline Derivatives Obtained Through Imino Diels-Alder Reactions as Potential Antitumoral Agents

  2010cited by this paper
• Catalytic Asymmetric Synthesis of Oxindoles Bearing a Tetrasubstituted Stereocenter at the C‐3 Position

  2010cited by this paper
• 3‐Alkenyl‐oxindoles: Natural Products, Pharmaceuticals, and Recent Synthetic Advances in Tandem/Telescoped Approaches (Eur. J. Org. Chem. 24/2010)

  2010cited by this paper
• Escape from flatland: increasing saturation as an approach to improving clinical success.

  2009cited by this paper
• Chiral Brønsted acid-catalyzed enantioselective three-component Povarov reaction.

  2009cited by this paper
• Recent synthetic developments in a powerful imino Diels–Alder reaction (Povarov reaction): application to the synthesis of N-polyheterocycles and related alkaloids

  2009cited by this paper
• Asymmetric Syntheses of Oxindoleand Indole Spirocyclic Alkaloid Natural Products

  2009cited by this paper
• A simple entry to novel spiro dihydroquinoline-oxindoles using Povarov reaction between 3-N-aryliminoisatins and isoeugenol

  2008cited by this paper
• Lewis acid catalyzed reaction of arylvinylidenecyclopropanes with ethyl (arylimino)acetates: a facile synthetic protocol for pyrrolidine and 1,2,3,4-tetrahydroquinoline derivatives.

  2007cited by this paper
• Pyrrolidinyl-spirooxindole natural products as inspirations for the development of potential therapeutic agents.

  2007cited by this paper
• Chiral Brønsted acid-catalyzed inverse electron-demand aza Diels-Alder reaction.

  2006cited by this paper
• Montmorillonite KSF‐Catalyzed One‐Pot, Three‐Component, Aza‐Diels–Alder Reactions of Methylenecyclopropanes with Arenecarbaldehydes and Arylamines

  2003cited by this paper
• The Lewis acids catalyzed aza-Diels-Alder reaction of methylenecyclopropanes with imines.

  2003cited by this paper
• Ketene dithioacetals in the aza-Diels-Alder reaction with N-arylimines: a versatile approach to tetrahydroquinolines, 2,3-dihydro-4-quinolones, and 4-quinolones.

  2002cited by this paper
• Three component coupling reactions of N-acetyl-2-azetine- rapid stereoselective entry to 2,3,4-trisubstituted tetrahydroquinolines.

  2002cited by this paper
• InCl(3)-catalyzed domino reaction of aromatic amines with cyclic enol ethers in water: a highly efficient synthesis of new 1,2,3,4-tetrahydroquinoline derivatives.

  2002cited by this paper
• First asymmetric synthesis of quinoline derivatives by inverse electron demand (IED) Diels-Alder reaction using chiral Ti(IV) complex.

  2001cited by this paper
• Alkaloids of Alstonia lanceolata

  1981cited by this paper

• Development of a Highly Selective Synthesis of 4-Substituted Tetrahydroquinolines: Substrate Scope and Mechanistic Study.

  2025cites this paper
• An [(IPr)AuCl]-catalyzed formal [4+2] process of N-Ar N,O-acetals with arylacetylenes for the construction of pyrrolo[1,2-a]quinolines.

  2025cites this paper
• Copper-catalyzed domino cyclization of anilines and cyclobutanone oxime: a scalable and versatile route to spirotetrahydroquinoline derivatives

  2025cites this paper
• Direct Access to Quinone-Fused 5-Substituted-1,4-Benzodiazepine Scaffolds from Azidoquinones with/without [1,2]-Azide-Nitrogen Migration: Mechanistic Insights.

  2023cites this paper
• Phosphine-catalyzed [5+1] annulation of β'-acetoxy allenoates: straightforward access to tetrahydroquinoline derivatives.

  2023cites this paper
• Silver‐Catalyzed Tandem Reaction of β‐Alkynyl Ketones toward Spiro[isochromene‐1,4′‐quinoline] with Anticancer Activities

  2023cites this paper
• Solvent-Free Mechanosynthesis of Polysubstituted 1,2-Dihydroquinolines from Anilines and Alkyne Esters.

  2022cites this paper
• Selective Synthesis of Pyrazolonyl Spirodihydroquinolines or Pyrazolonyl Spiroindolines under Aerobic or Anaerobic Conditions.

  2022cites this paper
• Employing Arylacetylene as a Diene Precursor and Dienophile: Synthesis of Quinoline via the Povarov Reaction.

  2021cites this paper
• Diastereoselective and Reversed Regioselective Annulations of N-Alkyl Anilines to Julolidines and Lilolidines.

  2020cites this paper
• Enantioselective Synthesis of 4-Allyl Tetrahydroquinolines via Copper(I) Hydride-Catalyzed Hydroallylation of 1,2-Dihydroquinolines.

  2020cites this paper
• Structural Diversity Attributed by Aza-Diels-Alder Reaction in Synthesis of Diverse Quinoline Scaffolds

  2019cites this paper
• Direct Synthesis of 2,3-Diaroyl Quinolines and Pyridazino[4,5- b]quinolines via an I2-Promoted One-Pot Multicomponent Reaction.

  2019cites this paper
• Progress in the Chemistry of Tetrahydroquinolines.

  2019cites this paper
• Substituted 1,5-naphthyridine derivatives as novel antileishmanial agents. Synthesis and biological evaluation.

  2018cites this paper
• Brønsted‐Acid‐Catalyzed Substrate‐Controlled and Site‐Selective Friedel–Crafts Alkylation: A New Strategy for Post‐Modification of 1,2‐Dihydroquinolines

  2017cites this paper
• Synergistic I2/Amine Promoted Povarov-Type Reaction for the Synthesis of 2-Acyl-3-aryl(alkyl)quinolines Using Aryl(alkyl)acetaldehydes as Alkene Surrogates.

  2017cites this paper
• A one pot three-component reaction for the preparation of dihydroquinolines with two different ketones and aromatic amines.

  2017cites this paper
• Study of the Hetero-[4+2]-Cycloaddition Reaction of Aldimines and Alkynes. Synthesis of 1,5-Naphthyridine and Isoindolone Derivatives.

  2017cites this paper