Cited by CBr4 as a Mild Oxidant‐Enabled Oxidation of a sp3 C−H Bond: A Facile Synthesis of the Persistent Iminium Salts of Tetrahydroisoquinolines

Pseudo Four-Component Synthesis of 5,6-Dihydroindolo[2,1-a]isoquinolines DOI

Almira R. Miftyakhova, Т. Н. Борисова, Артем Н. Фахрутдинов

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(2), P. 1045 - 1057

Published: Jan. 4, 2024

An easy synthesis of novel highly functionalized 5,6-dihydroindolo[2,1-a]isoquinolines was developed via a pseudo four-component domino reaction 1-aroyl-3,4-dihydroisoquinolines, terminal α,β-ynones, and malononitrile. The selective formation this biologically relevant heterocyclic core achieved using one-pot approach under microwave irradiation. the same skeleton through 5,6-dihydropyrrolo[2,1-a]isoquinolines with malonic acid dinitrile supports proposed mechanism, involving intermediate product three-component reaction. Furthermore, disproval an alternative pathway, which involved dimerization malononitrile followed by transformation, demonstrated. Introducing dimer as CH resulted in different pyrido[3′,4′:4,5]pyrrolo[2,1-a]isoquinoline core. Additionally, synthesized were examined for their photophysical properties, revealing attractive luminescent characteristics.

Language: Английский

Citations

Single-Electron Reduction of “Push–Pull” C–C Single Bond and Decyanation Using Tertiary Amines as the Organic Electron Donor DOI

Tong Li,

Zheng Sun, Shuwei Zhang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(4), P. 2516 - 2524

Published: Feb. 6, 2024

Using commercially available tertiary amines as an organic electron donor (OED), the reduction of "push–pull" C–C single bond and reductive decyanation tetrahydroisoquinolines were realized. These reactions exhibited higher reaction efficiency better functional group tolerance compared with those metallic reductants, mechanistic study indicated that a radical intermediate was involved in bond, which provides new way to OED-enabled mild reduction.

Language: Английский

Citations

Oxidants Controlled C−H Bond Functionalization of N‐Aryltetrahydroisoquinolines: The Construction of the Quaternary Carbon Center and Cleavage of the C−N Bond DOI

Yuqin Chen, Shuwei Zhang,

Tong Li

et al.

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 30(3)

Published: Oct. 25, 2023

Initiated by triarylamine radical cation salt (TBPA), the direct C-H bond functionalization of α-N-aryltetrahydroisoquinoline esters was smoothly realized, giving a series α-hydroxylated derivatives with quaternary carbon center in good yields. Differently, presence tert-butyl nitrite (TBN), C-N single cleaved to keto esters. The mechanistic study revealed that these reactions were mediated similar mechanism, which N-nitrosation might provide driving force cleavage.

Language: Английский

Citations

CBr₄ as a Mild Oxidant‐Enabled Oxidation of a sp³ C−H Bond: A Facile Synthesis of the Persistent Iminium Salts of Tetrahydroisoquinolines DOI

Yuqin Chen, Shuwei Zhang, Yuemei Li

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(14)

Published: Jan. 9, 2024

Using CBr

Language: Английский

Citations