Application of Organolithium and Related Reagents in Synthesis. Part 23: Synthetic Strategies Based on ortho-Aromatic Metallation. Synthesis of 4b-Arylisoindolo[2,1-a]quinoline derivatives

Application of Organolithium and Related Reagents in Synthesis, Part 24. Synthetic Strategies Based on Aromatic Metallation. A Concise Regiospecific Conversion of Benzoic Acids into 2-(1-Aryl-2-methoxycarbonylethyl)benzoic Acids

“…1-Methoxy-1-trimethylsiloxyethene was obtained according to a known procedure 12 from methyl acetate anion and chlorotrimethylsilane and it was used as a mixture with methyl(trimethylsilyl) acetate as impurity. The composition of the isomeric ratios were determined by 1…”

Methods for the construction of [1,2]isoindolo-condensed benzazepines, benzazocines, quinolines, and isoquinolines. 2. Isoindoloquinolines, isoindoloisoquinolines. (Review)

“…The starting compounds for the synthesis of the aza derivatives 6g-j are picoline and isonicotine anilides 3g-j, the reaction of which with butyllithium and DMF gives the intermediate 2-aryl-3-hydroxy-2,3-dihydroazaisoindol-1-ones 4g-j [3]. Isoindolo[2,1-a]quinolines can be obtained in one stage from 2-aryl-3-hydroxyisoindol-1-ones 10 [4]. The initial isoindolones 10 are synthesized by the lithiation of benzanilides with butyllithium in THF followed by reaction of the obtained salts 9 with carbonyl compounds.…”

Synthesis of dihydroisoindolo[2,1-a]quinolin-11-ones, their in silico ADMET properties and in vitro antitumor activities

“…4 Due to that few natural and synthetic examples of isoindoloquinoline models have been identied, their synthesis continues being attractive. Therefore, some methodologies as Grignard reaction, 5,6 ortho-aromatic metallation, 7 Suzuki coupling, 8 Friedel-Cras reaction from phthalimides, 9 Barbier-type allylation, 10 among others; have been effective for the isoindolo[2,1-a]quinoline synthesis. Moreover, phthalimide building block has showed an important role in almost all synthetic tools, becoming easily obtained from anilines and phthalic anhydride, further its derivatization towards IIQ synthesis.…”