34799-02-5

Upstream product

• 76306-42-8 1-methyl-3-phenyl-6,7-methylenedioxy-3,4-dihydroisoquinoline 
• 1083166-89-5 5-(1-azidoethyl)-6-(phenylethynyl)benzo[d][1,3]dioxole 
• 1402452-41-8 7-phenyl-[1,3]dioxolo[4,5-g]isoquinoline 6-oxide 
• 67-68-5 dimethyl sulfoxide 
• 15930-53-7 6-bromo-3,4-methylenedioxybenzaldehyde 
• 536-74-3 phenylacetylene 
• 437611-94-4 6-(phenylethynyl)benzo[d][1,3]dioxole-5-carbaldehyde 
• 98-80-6 phenylboronic acid 
• 114130-59-5 5-Methyl-[1,3]dioxolo[4,5-g]isoquinolin-7-ol 
• 16717-64-9 1-azidostyrene 

Relevant academic research and scientific papers

Iridium-Catalyzed Enantioselective and Diastereoselective Hydrogenation of 1,3-Disubstituted Isoquinolines

The development of a general method utilizing a hydroxymethyl directing group for asymmetric hydrogenation of 1,3-disubstituted isoquinolines to provide chiral 1,2,3,4-tetrahydroisoquinolines is reported. The reaction, which utilizes [Ir(cod)Cl]2 and a commercially available chiral xyliphos ligand, proceeds in good yield with high levels of enantioselectivity and diastereoselectivity (up to 95% ee and >20:1 dr) on a range of differentially substituted isoquinolines. Directing-group studies demonstrate that the hydroxymethyl functional group at the C1 position is more efficient at enabling hydrogenation in comparison to other substituents, although high levels of enantioselectivity were conserved across a variety of polar and nonpolar functional groups. By utilization of the generated chiral β-amino alcohol as a functional handle, the synthetic utility is further highlighted via the synthesis of 1,2-fused oxazolidine, oxazolidinone, and morpholinone tetrahydroisoquinolines in one step. Additionally, a non-natural analogue of the tetrahydroprotoberberine alkaloids was successfully synthesized.

Synthesis of Isoquinoline Derivatives via Palladium-Catalyzed C?H/C?N Bond Activation of N-Acyl Hydrazones with α-Substituted Vinyl Azides

A palladium-catalyzed cyclization of N-acetyl hydrazones with vinyl azides has been developed. Various substituted isoquinolines, including diverse fused isoquinolines can be prepared via this protocol in moderate to good yields. Mechanistic studies suggest that α-substituted vinyl azide serves as an internal nitrogen source. Also, C?H bond activation and C?N bond cleavage have been realized using hydrazone as directing group. (Figure presented.).

Bidentate Directing-Enabled, Traceless Heterocycle Synthesis: Cobalt-Catalyzed Access to Isoquinolines

Traceless heterocycle synthesis based on transition-metal-catalyzed C-H functionalization is synthetically appealing but has been realized only in monodentate directing systems. Bidentate directing systems allow for the achievement of high catalytic reactivity without the need for a high-cost privileged ligand. The first bidentate directing-enabled, traceless heterocycle synthesis is demonstrated in the cobalt-catalyzed synthesis of isoquinolines via 2-hydrazinylpyridine-directed C-H coupling/cyclization with alkynes. Convenient directing group installation through a ubiquitously present ketone group allows synthetic elaboration for complex molecules.

Palladium-catalyzed C-H oxidation of isoquinoline N-oxides: Selective alkylation with dialkyl sulfoxides and halogenation with dihalo sulfoxides

A novel palladium-catalyzed C-H oxidation of isoquinoline N-oxides has been developed for regioselectively synthesizing substituted isoquinolines. The method represents the first example of using dialkyl sulfoxides as the alkyl sources for the construction of 1-alkylated isoquinolines. Moreover, the regioselective halogenation of isoquinoline N-oxides is also successful using dihalo sulfoxides as the halide sources. Copyright

Gold-catalyzed synthesis of isoquinolines via intramolecular cyclization of 2-alkynyl benzyl azides

Intramolecular cyclization of 2-alkynyl benzyl azides in the presence of AuCl3 and AgSbF6 in THF under a pressured vial at 100 °C gives the corresponding isoquinolines in good yields. Similarly, the five-membered analogs afford the c