Synthesis of O-Substituted Benzophenones by Grignard Reaction of 3-Substituted Isocoumarins

Abstract

A series of o-substituted benzophenones was prepared by efficient method involving the 3-substituted isocoumarins and phenylmagnesium bromide. The reaction was completed in presence of anhydrous ether under dry ice-solvent bath in few hours with modest to good yields.

Facile benzannulation of isocoumarins in the efficient synthesis of diversified 1,3-disubstituted isoquinolines

“…Recently, we have reported the synthesis of diketones by the Grignard reaction of 3-substituted isocoumarin [24,25]. As an extension of this study, here we report the intramolecular cyclization of diketones (formed from isocoumarins via the Grignard reaction and without isolating the product from the reaction mixture) using ammonium acetate and Montmorillonite K-10 acidic catalyst.…”

“…As a continuation of our research interest in isoquinolines and other heterocyclics [24][25][26][27][28][29][30][31][32][33][34][35][36][37][38][39][40][41], the synthesis of a series of 1,3-disubstituted isoquinolines is reported. The reaction of isocoumarin 1 with various Grignard reagents, 2 in tetrahydrofuran at -30 to 25°C for 1h (RT) afforded diketones, which without isolating from the reaction mixture, further treated with ammonium acetate and in the presence of Montmorillonite K-10 catalyst, and ethanol solvent at 70°C afforded 1,3-disubstituted isoquinolines 4 in good yields (Scheme 1).…”

Ligand-free, PdCl2(PPh3)2 catalyzed, microwave-assisted Suzuki coupling of 1-chloro-3-phenylisoquinoline in the synthesis of diversified 1,3-disubstituted isoquinolines

“…In our continued interest on isoquinolines and heterocyclics [33][34][35][36][37][38][39][40][41][42][43][44][45][46][47][48], the present study involved the Suzuki coupling, in order to explore an efficient catalytic system in the synthesis of diversified 1,3-disubstituted isoquinolines. The optimization envisaged that the use of PdCl 2 (PPh 3 ) 2 catalyst, Na 2 CO 3 base, and 1,4-dioxane solvent under aqueous-free microwave irradiation conditions offered greater efficiency in the synthesis of 1,3-disubstituted isoquinolines.…”

SnO2 nanoparticles mediated nontraditional synthesis of biologically active 9-chloro-6,13-dihydro-7-phenyl-5H-indolo [3,2-c]-acridine derivatives

“…In continuation of our interest in synthesis of biologically active heterocyclics Manivel et al, 2008), a number of 9-chloro-6,13-dihydro-7-phenyl-5H-indolo [3,2-c] acridine analogues has been synthesized and examined for their bioactivities. In the present investigation, the hemolytic and cytotoxicity potential of 9-chloro-6,13-dihydro-7-phenyl-5H-indolo [3,2-c] alcidine analogues against human erythrocytes, HeLa and Vero cells were explored.…”