An efficient synthesis of pyrrolo[2,1-a]isoquinoline derivatives containing coumarin skeletons via a one-pot, three-component reaction

3-(Bromoacetyl)coumarins: unraveling their synthesis, chemistry, and applications

“…Several brominating agents have been reported in the last two decades such as tetrabutylammonium tribromide (TBATB), bromine, phenyltrimethylammonium tribromide (PhTAPBr 3 ), N-bromosuccinimide (NBS), and copper(II) bromide (CuBr 2 ) (Scheme 1). [35][36][37][38][39][40][41][42][43][44][45][46][47]…”

“…An efficient synthesis of poly functionalized coumarin bearing pyrrolo[2,1- a ]isoquinoline derivatives 44 was achieved via a multi-reaction of 3-(bromoacetyl)coumarin derivatives 1, isoquinoline 42, and dimethyl acetylenedicarboxylate 43 under the influence of triethylamine as catalyst ( Scheme 21 ). 78 …”

Synthesis, Antioxidant, Anticholinesterase Activities and Molecular Docking Studies of coumaryl 1,3-selenazoles Derivatives

“…A mixture of 3-acetylcoumarin derivatives (10 mmol, 1.880 g), NBS (11 mmol, 1.958 g) and ptoluenesulfonic acid (1 mmol, 172 mg) in chloroform: acetonitrile (25:5) was magnetically stirred at reflux. After completion of the reaction [about 4 h; TLC (Hexane/Ethyl acetate at a ratio of 9:1)], the mixture was cooled, and the precipitate was filtered and washed with ethanol (10 mL) to afford the pure product 3-(2-bromoacetyl) coumarin derivatives [28].…”

“…This reaction is called Knoevenagel condensation, which results in the formation of a lactone ring and removal of water. Then, they were brominated with N-bromosuccinamide, NBS in chloroform: acetonitrile (20:4) in the presence of p-toluenesulfonic acid, PTSA as a catalyst and were refluxed for 4 hours to give compounds 3b-3e [28]. After that, 2-Amino-4-(coumarin-3-yl) selenazoles derivatives (4a-4e) were obtained by the reactions of 3a-3e with selenourea in methanol: water (1:1) at room temperature with stirring and sodium fluoride as the catalyst [23,29].…”

A Convenient Approach for the Synthesis of 1,3-Diphenyl-1H-pyrazole-5-carbonitrile

“…In continuation of our interest in 1,3-dipolar cycloaddition reactions, [21][22][23][24] we describe herein our efforts toward the synthesis of 1,3-dipheny pyrazoles using a 1,3-dipolar cycloaddition protocol to achieve a one-pot, three-component coupling of 4-oxo-4H-chromene-3-carbaldehyde, hydroxylamine hydrochloride, and hydrazonoyl chloride to yield 1,3,4-trisubstituted pyrazoles 2 (Scheme 1). To the best of our knowledge, there have been no previous reports concerning the reaction of hydrazonoyl chloride with 4oxo-4H-chromene-3-carbonitrile for the direct construction of pyrazole structures.…”