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

Organic Letters, Journal Year: 2019, Volume and Issue: 21(8), P. 2708 - 2711

Published: April 2, 2019

The first synthesis of 2,3-diaroyl quinolines via a formal [3 + 2 1] cycloaddition enaminones, aryl methyl ketones, and amines is disclosed. This reaction efficiently affords 1,4-dicarbonyl scaffold, which useful building block for constructing complex fused heterocycles. Furthermore, the scaffold has been used directly to prepare pyridazino[4,5-b]quinoline skeletons in one-pot.

Language: Английский

---

Metal-Free C–N or C–C Bond Cleavages of α-Azido Ketones: An Oxidative-Amidation Strategy for the Synthesis of α-Ketothioamides and Amides

The Journal of Organic Chemistry, Journal Year: 2019, Volume and Issue: 84(22), P. 14883 - 14891

Published: Oct. 14, 2019

A novel metal-free oxidative-amidation strategy for the synthesis of α-ketothioamides and amides from α-azido ketones was developed. The C–H bond thionation with elemental sulfur could form α-ketothioacyl azide, which then nucleophilically attacked by amines, causing cleavage C–N to afford α-ketothioamides, while be formed release nitrogen gas cyano anion in presence PhI(OAc)2 selective C–C cleavage.

Language: Английский

---

Synthesis of 2,1-Benzoisoxazole-Containing 1,2,3-Triazoles through Copper-Catalyzed Three-Component Domino Reactions of o-Bromoacetophenones, Aldehydes, and Sodium Azide

The Journal of Organic Chemistry, Journal Year: 2020, Volume and Issue: 85(4), P. 2688 - 2696

Published: Jan. 3, 2020

We herein describe an efficient copper-catalyzed three-component domino protocol used to prepare 2,1-benzoisoxazole-containing 1,2,3-triazoles from commercially available o-bromoacetophenones, aldehydes, and sodium azide. This process involves Aldol condensation, azide-chalcone oxidative cyclization, 1,2,3-triazole-assisted azidation, denitrogenative cyclization sequences. The formed compounds could be considered as benzo[c]isoxazole-functionalized combretastatin A-4 triazole analogues, which might potential applications in the discovery of a new anticarcinogen.

Language: Английский

---

A Compilation of Synthetic Strategies to Access the Most Utilized Indoloquinoline Motifs

Chemistry - An Asian Journal, Journal Year: 2022, Volume and Issue: 17(7)

Published: Feb. 8, 2022

Indoloquinoline alkaloids constitute an important class of aromatic heterocycles consisting quinoline and indole fused together in various orientations. These compounds, both natural synthetic, often display bioactivities which have established them to be one the interesting medicinal targets. This compounds stimulated much interest among synthetic chemists as evidenced by growth number methods prepare study this alkaloids. review compiles strategies currently known literature for construction four indoloquinoline skeletons.

Language: Английский

---

2-Azidobenzaldehyde-Based [4+2] Annulation for the Synthesis of Quinoline Derivatives

Molecules, Journal Year: 2024, Volume and Issue: 29(6), P. 1241 - 1241

Published: March 11, 2024

Quinoline is a privileged heterocyclic ring which can be found in many drug molecules and bioactive compounds. The development of synthetic methods for making quinoline derivatives continuously attracts the interest organic medicinal chemists. This paper highlights 2-azidobenzaldehyde-based [4+2] annulation synthesis including fused spiro-quinolines, quinoline-4-ols, 4-aminoquinolines, related

Language: Английский

---

Hyperconjugation‐Driven Isodesmic Reaction of Indoles and Anilines: Reaction Discovery, Mechanism Study, and Antitumor Application

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(47)

Published: Aug. 23, 2024

Abstract Isodesmic reactions, in which chemical bonds are redistributed between substrates and products, provide a general powerful strategy for both biological synthesis. However, most isodesmic reactions involve either metathesis or functional‐group transfer. Here, we serendipitously discovered novel reaction of indoles anilines that proceeds intramolecularly under weakly acidic conditions. In this process, the five‐membered ring indole motif is broken new constructed on aniline side, accompanied by formation motif. Mechanistic studies revealed pivotal role σ→π* hyperconjugation nitrogen atom driving unusual reaction. Furthermore, successfully synthesized diverse series polycyclic derivatives; among quinolines, potential antitumor agents were identified using cellular vivo experiments, thereby demonstrating synthetic utility developed methodology.

Language: Английский

---

Metal-free three-component synthesis of thioamides from β-nitrostyrenes, amines and elemental sulfur

Tetrahedron Letters, Journal Year: 2021, Volume and Issue: 74, P. 153092 - 153092

Published: April 17, 2021

Language: Английский

---

Copper Catalyzed Synthesis of 3‐Nitro‐Quinolines from Nitro‐Olefins and Anthranils: Its Application in the Synthesis of Quindoline

Advanced Synthesis & Catalysis, Journal Year: 2021, Volume and Issue: 364(1), P. 41 - 46

Published: Oct. 1, 2021

Abstract Copper‐catalyzed routes have been achieved for the synthesis of 3‐nitroquinolines from readily available nitroolefins and anthranils. This reaction proceeds via [4+2] cycloaddition between anthranils nitro‐styrenes under mild conditions to obtain biologically important heterocycles. A wide range diversely substituted nitro‐olefins are successfully employed in this access a series 3‐nitro‐quinolines 81–93% yields. The synthetic utility present methodology is also illustrated manuscript. magnified image

Language: Английский

---

Facile access to 3-sulfonylquinolines via Knoevenagel condensation/aza-Wittig reaction cascade involving ortho-azidobenzaldehydes and β-ketosulfonamides and sulfones

Beilstein Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 19, P. 800 - 807

Published: June 9, 2023

Quinoline-based sulfonyl derivatives, and especially sulfonamides, are relevant promising structures for drug design. We have developed a new convenient protocol the synthesis of 3-sulfonyl-substituted quinolines (sulfonamides sulfones). The approach is based on Knoevenagel condensation/aza-Wittig reaction cascade involving o-azidobenzaldehydes ketosulfonamides or ketosulfones as key building blocks. appropriate both ketosulfonyl reagents α-sulfonyl-substituted alkyl acetates providing target quinoline derivatives in good to excellent yields.

Language: Английский

---

Dimerization–cyclization reactions of isocyanoaryl-tethered alkylidenecyclobutanes via a triplet biradical mediated process

Organic Chemistry Frontiers, Journal Year: 2020, Volume and Issue: 7(18), P. 2634 - 2643

Published: Jan. 1, 2020

A triplet biradical mediated dimerization–cyclization reaction of isocyanoaryl-tethered alkylidenecyclobutanes to construct macrocyclic skeletons including dihydroquinoline and quinoline units has been reported.

Language: Английский

---