Synthesis of Indole-Dihydroisoquinoline Sulfonyl Ureas via Three-Component Reactions

Abstract

Isoquinolines activated with sulfamoyl chlorides were reacted with indoles in a 3-component reaction to generate a library of dihydroisoquinoline derivatives. Using a differential protecting group strategy, products could be further derivatised. Synthesis of isoquinoline starting materials using several different methods is also described.

Nickel-Catalyzed Ligand-Free Hiyama Coupling of Aryl Bromides and Vinyltrimethoxysilane

“…Among these solvents, DMF is the best choice. The use of different divalent nickel sources gave similar reaction outcomes (entries [11][12]. Increasing the amount of vinylsilane and base to 2.3 equivalent could improve the yield to 87% (entry 13, 84% isolated yield).…”

“…Yellow oil, 20.2 mg, yield: 69%. 6-vinylisoquinoline (4b) [12] The reaction was performed following GP3. Colorless liquid, 20.0 mg, yield: 70%.…”

“…In order to address the abovementioned issues, numerous transition-metal-catalyzed cross-coupling reactions using readily available aryl halides have been developed to access styrenes in the past several decades. 9 For example, tremendous Pd-catalyzed the vinylation of aryl halides using magnesium 10 -, lithium 11 -, aluminium 12 -, boron 13 -, silicon 14 -and tin 15 -based vinyl donors has been reported and widely applied to the synthesis of vinyl arenes (Scheme 1a). However, these methods generally suffer from the use of noble metal, expensive and sensitive ligand, and in some cases using toxic or unstable organometallic reagents.…”

Pseudo-irreversible butyrylcholinesterase inhibitors: Structure–activity relationships, computational and crystallographic study of the N-dialkyl O-arylcarbamate warhead

“…1H-Indol-7-ol [89] (92 mg, 0.692 mmol), TBDMSCl (1.1 eq., mg), and imidazole (1.2 eq., 56 mg) in DMF (2 mL) were stirred at rt under Ar for 18 h. 7-((Tert-butyldimethylsilyl)oxy)-1H-indole [90] was isolated by column chromatography on silica (1. PE; 2.…”