Introduction of Diverse Functional Groups to Isoquinolines by Microwave‐assisted Transition Metal‐catalyzed Coupling Reactions

Abstract

Diverse functional groups were introduced in isoquinolines under microwave-assisted palladium-or copper-catalyzed coupling reactions, which include functional groups to isoquinoline were achieved with 1-substituted 4-and 7-bromoisoquinolines, arylboronic acids, terminal alkenes, terminal alkynes, and azaheterocycles. 1,4-or 1,7-Disubstituted isoquinolines were obtained in moderate to excellent yields within 1 h under microwave irradiation. The facile functional group modification of isoquinoline core could establish isoquinoline compound library for drug discovery.

Recent Advances in Microwave-Assisted Copper-Catalyzed Cross-Coupling Reactions

“…and Yum, E.K. have developed microwave assisted synthesis of isoquinolines using copper(I) oxide (Cu 2 O) [24]. They have systematically optimized the reaction using different kind and equivalent of the catalyst, base, solvent, and reaction time.…”

Microwave‐assisted Transition Metal‐catalyzed Coupling Approach to Indazole Diversity

“…Microwave-assisted Palladium-catalyzed Aryl-Aryl Coupling reactions 27 . tert-Butyl 3,6-dibromo 1H-indazole-1-carboxylate (0.5 mmol), Na 2 CO 3 (2.0 mmol), arylboronic acid (2.0 mmol), Pd(PPh 3 ) 2 Cl 2 (10 mol %), and 1,4-dioxane: ethanol:water = 6:2:1 (5 mL) were added to 10 mL vial.…”

“…[11][12][13][14][15][16][17][18][19] Recently, palladium-catalyzed coupling methods have shown essential synthetic tools for functionalization and formation of variety heterocycles. [23][24][25][26][27] In drug discovery research, establishment of functionally diversified small molecule compound library is very efficient way to find biologically active substances with biomolecular targets. [23][24][25][26][27] In drug discovery research, establishment of functionally diversified small molecule compound library is very efficient way to find biologically active substances with biomolecular targets.…”

“…Recently, palladium–catalyzed coupling methods have shown essential synthetic tools for functionalization and formation of variety heterocycles . Our reported microwave‐assisted copper or palladium‐catalyzed diversification of heterocycles boasts significant advantages over conventional heating . In drug discovery research, establishment of functionally diversified small molecule compound library is very efficient way to find biologically active substances with biomolecular targets .…”

Microwave‐assisted Synthesis of 5,6,7‐Trisubstituted Pyrrolo[2,3‐d]Pyrimidines via Palladium‐catalyzed Heteroannulation with Internal Alkynes

“…Microwave irradiation in organic syntheses has attracted considerable attention for its ability to accelerate inherently slow thermal reactions, resulting in significant energy savings, high chemical yields, and cleaner reactions with shorter reaction times . We also reported previously that microwave‐mediated palladium or copper‐catalyzed diversification of heterocycles has significant advantages over conventional heating . Thus far, one‐pot synthetic methods of creating trisubstituted pyrrolo[2,3‐ d ]pyrimidines have been limited.…”