A convenient synthesis of quinolines by reactions of o-isocyano-β-methoxystyrenes with nucleophiles

RuCl2(dmso)4 Catalyzes the Solvent‐Free Indirect Friedländer Synthesis of Polysubstituted Quinolines from Alcohols

“…R f = 0.67 (hexane/ethyl acetate 4:1). 1 [33] Yellow oil (0.56 g, 85 %), t r = 20. [33] Phenyl-1,2,3,4-tetrahydroacridine (3j): [36] Pale yellow solid (0.48 g, 92 %), m.p.…”

“…1 H NMR: δ = 1.75-1.85, 1.95-2.00, 2.60 and 3.18 [2 ϫ m and 2 ϫ t, respectively, J = 6.7 and 7 Hz, respectively, 2 H each, (CH 2 ) 4 ], 7.20-7.30, 7.40-7.60 and 7.98 (2 ϫ m and d, respectively, J = 8.0 Hz, 4, 4 and 1 H, respectively, ArH) ppm. 13 [38] 4-Methyl-2-phenylquinoline (3m): [33] 2-(tert-Butyl)-6-chloro-4-phenylquinoline (3p): [33] Pale yellow oil (0.47 g, 79 %), t r = 17.9. R f = 0.75 (hexane/ethyl acetate 4:1).…”

A Novel Synthesis of Quinazolines by Cyclization of 1‐(2‐Isocyanophenyl)alkylideneamines Generated by the Treatment of 2‐(1‐Azidoalkyl)phenyl Isocyanides with NaH

“…2-(Aminophenyl)(4-chlorophenyl)methanone [10], (2-amino-5-chlorophenyl)(4-methylphenyl)methanone [11], (2-amino-5-methoxyphenyl)phenylmethanone [12], N-[2-ethanoylphenyl]formamide [13], N-(2-benzoylphenyl)formamide [14], N-[3-chloro-6-(chloromethyl)phenyl]formamide [7], N-[2-(azido-Scheme 2 methyl)phenyl]formamide (1a) [6], N-(4-benzoylpyridin-3-yl)formamide [8], and N-[4-(4-chlorobenzoyl)pyridin-3-yl]formamide [9] were prepared according to the reported procedures. All other chemicals used in this study were commercially available.…”

“…(2-Amino-4-chlorophenyl) ( N-(2-Acylphenyl)formamides were prepared by N-formylation of the respective 2-aminophenyl ketones with HCO 2 H as described in [14]. (1.1 g, 9.0 mmol) in THF (5 ml) dropwise.…”

Rare‐Earth Metal Chlorides Catalyzed One‐pot Syntheses of Quinolines under Solvent‐free Microwave Irradiation Conditions

“…28-8.19 (m, 3H), 7.93-7.72 (m, 4H), 7.56-7.50 (m, 8H); 13 C NMR (CDCl 3 , 75.0 MHz) δ: 156. 9, 153.5, 149.3, 148.8, 139.6, 138.4, 130.1, 129.6, 129.4, 128.9, 128.6, 128.4, 127.6, 126.4, 125.7, 119.4, 115 [25] Yield 91%; yellow solid.…”