Three-component coupling reactions of isoquinolines, dimethyl acetylenedicarboxylate and indoles: a facile synthesis of 3-indolyl-1,2-dihydro-2-isoquinolinyl-2-butenedioate

A three-component reaction between azaarenes (phenanthridine, quinoline or isoquinoline), acetylenic esters and phenol derivatives

“…The reaction between azaarenes (phenanthridine 1, isoquinoline 5 or quinoline 9) and acetylenic esters 2, 6 or 10 as a Michael acceptor [19][20][21][22][23][24] was undertaken in the presence of phenol derivatives (2,5-dimethylphenol, 2,4-di-tert-butylphenol, 4methylphenol and 4-chloro-3,5-dimethylphenol) at ambient temperature (see Scheme 2 and Table 1). Reactions were carried out by first mixing the phenanthridine, isoquinoline or quinoline and phenol derivatives and then the acetylenic ester was added slowly.…”

A Mild and Efficient Method to Functionalize Azines (Quinoline, Isoquinoline, and Phenanthridine) Using Acetylenic Esters and Heterocyclic NH or 1,3‐Dicarbonyl Compounds

“…The reaction of azines (phenanthridine 1 , isoquinoline 5 , or quinoline 9 ) with acetylenic esters 2 , 6 , or 10 as a Michael acceptor was undertaken in the presence of heterocyclic NH compounds (benzotriazole, 2‐methylbenzimidazole, maleimide, indole, 2‐methyl indole, 2‐benzoxazolinone, and 6‐chlorobenzoxazo‐linone) or 1,3‐dicarbonyl compound such as 5,5‐dimethyl‐1,3‐cyclohexadione at RT. Reactions were carried out by first mixing the phenanthridine, quinoline, or isoquinoline and heterocyclic NH or 1,3‐dicarbonyl compounds, and then, the acetylenic ester was added slowly.…”

Synthesis under Microwave Irradiation of [1,2,4]Triazolo[3,4-b] [1,3,4]thiadiazoles and Other Diazoles Bearing Indole Moieties and Their Antimicrobial Evaluation

“…The interest in developing syntheses of [1,2,4]triazolo[3,4- b ] [1,3,4]thiadiazoles is due to the fact that these compounds are potent antioxidants and anticancer agents [ 9 ] and have other pharmacological activities [ 10 ]. On the other hand, the chemistry of indole derivatives has been the subject of much interest in recent years due to the use of this ring system as the core structure in many heterocyclic compounds covering wide range of pharmacological applications [ 11 , 12 ]. Merging of these two bioactive components, [1,2,4]triazolo[3,4- b ][1,3,4]-thiadiazole and indole, in one system affords a compact structure with promising potential antimicrobial activities.…”