2-Chloroquinoline-3-carbaldehydes: synthesis and reactions (2012-2017)

Abstract

This review discuss in details the synthesis and reactions of 2-chloroquinoline-3-carbaldehydes during years of 2012-2017. The reactions are subdivided into groups, according to type of reaction, including reactions of both chloro and/or aldehyde substituents. Most applied reactions have been successfully utilized for synthesis of different biologically and pharmacologically active derivatives.

Synthesis and Biological Evaluation of Quinoline‐Based Novel Aurones

“…Initially commercially available aniline derivatives 1(a–n) were acylated by refluxing in a solution of glacial acetic acid and acetic anhydride for about one hour to obtain acetanilide derivatives 2(a–n) . Subsequently, these acetanilides were converted to 2‐chloroquinoline‐3‐carbaldehydes 3(a–n) by well‐known Vilsmeier‐Haack reaction …”

Cyanopyridinone- and Cyanopyridine-Based Cancer Cell Pim-1 Inhibitors: Design, Synthesis, Radiolabeling, Biodistribution, and Molecular Modeling Simulation

“…The reported synthetic intermediate 2-chloroquinoline-3-carbaldehyde ( 1 ) has received considerable attention in the synthesis of large numbers of heterocyclic systems . It was synthesized by cyclization of N -phenylacetamide with Vilsmeier′s reagent DMF/POCl 3 via a multicomponent reaction that involves chlorination, formylation, and cyclization.…”

“…The reported synthetic intermediate 2-chloroquinoline-3-carbaldehyde ( 1 ) has received considerable attention in the synthesis of large numbers of heterocyclic systems. 30 It was synthesized by cyclization of N -phenylacetamide with Vilsmeier′s reagent DMF/POCl 3 via a multicomponent reaction that involves chlorination, formylation, and cyclization. A one-pot four-component reaction was adopted in the synthesis of 6-((un)substituted phenyl)-4-(2-chloroquinolin-3-yl)-2-oxo-1,2-dihydropyridine-3-carbonitrile derivatives ( 3a–e ).…”

DABCO-catalyzed highly regioselective synthesis of novel 4H-pyrano[2,3- b]quinoline derivatives: three‑component domino strategy

“…Various types of polyfunctional quinoline derivatives are synthesized using 2-chloroquinoline-3carbaldehydes as a synthon [30][31][32]. Notably, over the last two decades, a wide range of derivatives of quinoline-fused heterocyclic compounds such as pyrrolo [3,4-b]quinolinone [33], pyrazoloquinolines [34], tetrazoloquinolines [35], pyranoquinolinones [36], thiopyranoquinolines [37], dihydrodibenzo [1,8]naphthyridinones [38], pyrimido [1,8]naphthyridines, chromenoquinolinyl-pyrimidines [39], pyrazolopyrano-quinolinyl-pyrimidines [40], and oxazepinoquinolines [41] have been reported.…”