Bichalcophenes: A concise synthesis of formyl ester‐ and cyano ester‐substituted bithiophenes, bifurans, and furanothiophenes

Abstract

Syntheses of new formyl ester- and cyano ester-substituted bithiophenes, bifurans, and furanothiophenes in good yield are described. The key synthetic step uses Stille coupling of appropriately substituted bromo 5-ring heterocycles with stannyl-substituted 5-ring heterocycles.

Indole and Benzimidazole Bichalcophenes: Synthesis, DNA Binding and Antiparasitic Activity

“…Synthesis of the indole-bichalcophene diamidine derivatives 4a-d is outlined in Scheme 1 . The bis-nitriles 3a-d were prepared by Stille coupling [11] , [12] , [13] reaction between the bromo derivatives 1a-d and 2-(trimethylstannyl)-1-( tert -butoxycarbonyl)- 1 H -indole-6-carbonitrile 2 using palladium tetrakistriphenylphosphine as a catalyst. The bis-nitriles 3a-d on reaction with a THF solution of lithium bis(trimethylsilyl)amide [14] , followed by treatment with ethanolic HCl yielded the hydrochloride salts of the diamidines 4a-d .…”

Facile Synthesis of Aryl-Pyridyl, Pyridazinyl, Pyrazinyl, and Triazinyl Acetonitriles

“…Also applying Stille coupling methodology between the acetonitrile ( 4 ) and 2‐(tri‐ n ‐butyltin)furan in the presence of 5 mol % of Pd(PPh 3 ) 4 using 1,4‐dioxane as solvent afforded compound ( 5g ) in good yield (88%).…”

Heterocyclic Diamidine DNA Ligands as HOXA9 Transcription Factor Inhibitors: Design, Molecular Evaluation, and Cellular Consequences in a HOXA9-Dependant Leukemia Cell Model

“…To a stirred solution of the bromo compounds (10 mmol), 5-(dimethoxymethyl)­furan-2-yl-tri- n -butylstannane (10 mmol) in 30 mL anhydrous 1,4-dioxane was added tetrakis-triphenylphosphine palladium (300 mg). The stirred mixture was warmed to 90–100 °C for 16 h. The solvent was removed under reduced pressure; the residue was extracted using 200 mL of dichloromethane (DCM) from aqueous solution containing 3 mL of concentrated ammonia, then washed with water, and passed through celite.…”