Microwave‐Assisted, One‐Pot Three‐Component Synthesis of 6‐(Pyrrolyl) Coumarin/Quinolone Derivatives Catalyzed by In(III) Chloride

Abstract

A series of 6‐(pyrrolyl) coumarin/quinolone derivatives have been synthesized in moderate to good yields (53‐79%) via one‐pot three‐component reactions of 6‐amino coumarin/quinolones, β‐nitrostyrenes and dialkyl acetylenedicarboxylates catalyzed by indium(III) chloride under microwave heating conditions.

Recent developments on microwave-assisted organic synthesis of nitrogen- and oxygen-containing preferred heterocyclic scaffolds

“…A microwave-irradiated multi-component synthesis of 6-(pyrrolyl) coumarin derivatives was reported by Ansary and co-workers. 129 They performed the initial model reaction with 6-amino coumarin 153a , β-nitrostyrene 154b and diethyl acetylenedicarboxylate 155a to form 6-(pyrrolyl) coumarin 156a . They obtained best result (75% yield) when InCl 3 was used as a catalyst in ethanol under microwave conditions at 100 °C for 1 h. After investigation of reaction conditions, they synthesized a series of 6-(pyrrolyl) coumarin derivatives 156a–j in 53–79% isolated yields using 6-amino coumarins 153a–b , β-nitrostyrenes 154a–d , and dialkyl acetylenedicarboxylates 155a–d (Scheme 55).…”

Use of Dialkyl Acetylenedicarboxylates in the Multicomponent Synthesis of Heterocyclic Structures

“…The reaction of 6‐aminocoumarin/quino‐lones 24 , β ‐nitrostyrenes 25 and dialkyl acetylenedicarboxylate 1 in the presence of 30 mol % of InCl 3 in ethanol under microwave heating condition at 100 °C afforded the corresponding products in good to high yields (Scheme 10). [19] …”

“…[18] Inasmuch as, coumarines and quinolones are typical heterocyles, they exist in many natural products which have biological activities including: antibacterial, antiviral, antimicro- The reaction of 6-aminocoumarin/quino-lones 24, β-nitrostyrenes 25 and dialkyl acetylenedicarboxylate 1 in the presence of 30 mol % of InCl 3 in ethanol under microwave heating condition at 100 °C afforded the corresponding products in good to high yields (Scheme 10). [19] A green and significant approach was developed in 2019 by Balu Atar et al for the synthesis of tetra-substituted pyrrols 27 by utilizing DBAL-2 via the one-pot reaction of dialkyl acetylenedicarboxylate 1, amines 2 and β-nitrostyrene 25 at room temperature under solvent-free condition (Scheme 11). [20] A green and effective method was developed in 2021 by Nazeri et al for the synthesis of substituted pyrroles 29 from the reaction of 5-amino-pyrazoles 28, aldehydes 6, dialkyl acetylenedicarboxylate 1 and isocyanides 12 in the presence of PTSA .…”

Microwave assisted synthesis of five membered nitrogen heterocycles

“…A new microwave assisted protocol for the synthesis of 6-(pyrrolyl)coumarin/quinolone derivatives 24 through an indium(III) catalysed one pot three component reaction (6-amino coumarin/quinolones 21, dialkyl acetylene dicarboxylates 23, and b-nitrostyrenes 22) (Scheme 7) was reported by Ansary et al 18 They applied this protocol under optimized reaction condition (21 (100 mg, 1.0 equiv. ), 22 (1.2 equiv.…”