Synthesis of 3‐Iodoquinolines by Copper‐Catalyzed Tandem Annulation from Diaryliodoniums, Nitriles, and 1‐Iodoalkynes

Abstract

An ovel method for the synthesis of 3-iodoquinolines was developed by copper-catalyzed tandem annulation from diaryliodoniums,n itriles, and 1-iodoalkynes.I ti samethod that is character-ized by the most convenient operation andw ide moleculardiversity.Copies of the 1 HNMR and 13 CNMR spectra for all compounds and 1a-1z and 1aa and the CIF file for the single crystalX -ray diffraction analysis of 1u are available in the Supporting Information.

Diaryliodonium(iii) salts in one-pot double functionalization of C–IIIIandorthoC–H bonds

“…Wang and Hu's group employed 1-halogeneted alkynes 62 to prepare 3-halogenated quinolines 63 , which can be derivatized to C-3 substituted quinolines via further transformations, such as catalytic coupling reactions (Scheme 22a). 55 Park and coworkers synthesized 4-aminoquinolines 65 using ynamides 64 as the alkyne components in the presence of a CuTC catalyst at 75 °C (Scheme 22b). 56 Furthermore, the obtained 65 were converted to the corresponding quinolinylmethanesulfonamides via [1,3]-rearrangement.…”

Cu-Catalyzed Cascade Annulation of Diaryliodonium Salts and Nitriles: Synthesis of Nitrogen-Containing Heterocycles

“…Based on literature reports, [21][22][23][24][25][26][27][28][29][30][31][32][33][34][35] there is one general mechanism for these cascade annulations (Scheme 1). First oxidative insertion of Cu(I) into the aryl-iodine bond with the higher reactivity of diaryliodonium salts would generate a highly electrophilic aryl-Cu(III) species, with subsequent interaction with nitriles producing a key intermediate N-arylnitrilium cation and Cu(I).…”

“…However, 1-iodoalkyne was used and a lower temperature was employed due to the lower thermal stability and higher reactivity of 1-iodoalkyne than terminal alkynes (Scheme 5). 27 This reaction can introduce an iodine atom to the C3 position of quinolines, and utilizes a broad scope of diaryliodonium salts and nitriles to give the desired Scheme 3 Proposed mechanism for the synthesis of quinolines…”

Single‐Step Synthesis of 3‐Iodoquinolines from 2‐Aminophenyl Ketones through a Regioselective (6‐endo‐dig) Electrophilic Cyclization

“…In recent years, the iodine‐mediated electrophilic cyclization of a heteroatom nucleophile with a tethered alkyne has been shown as an effective method for the synthesis of a large number of heterocyclic molecules . While searching for reported methods for the synthesis of 3‐iodoquinolines, we found few available reports for the iodocyclization of tethered alkynes with a nucleophilic amine (Figure ). Among these reports, for example, Flynn et al described the electrophilic iodocyclization of 1‐[2‐(dimethylamino)aryl]‐2‐yn‐1‐ols [Figure , Equation (1)].…”