Acid-Promoted Redox-Annulation toward 1,2-Disubstituted-5,6-dihydropyrrolo[2,1-α]isoquinolines: Synthesis of the Lamellarin Core DOI Creative Commons

Guo-Quan Hou,

Wenyan Zhao, Changjiang Deng

et al.

ACS Omega, Journal Year: 2022, Volume and Issue: 7(42), P. 37050 - 37060

Published: Oct. 14, 2022

An efficient synthesis of a variety 1,2-disubstituted-5,6-dihydropyrrolo[2,1-α]isoquinoline derivatives via an acid-promoted cyclization reaction between 1,2,3,4-tetrahydroisoquinoline (THIQ) and substituted α,β-unsaturated aldehyde is reported. This cycloaddition allows access to structurally diverse multisubstituted dihydropyrrolo[2,1-α]isoquinolines in moderate good yields, which was the core scaffold marine natural alkaloid lamellarins.

Language: Английский

Visible-light promoted radical cascade cyclization of 3-allyl-2-arylquinazolinones for the synthesis of phosphorylated dihydroisoquinolino[1,2-b]quinazolinones DOI
Jun Huang,

Caijin Ban,

J. J. Qin

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(62), P. 8119 - 8122

Published: Jan. 1, 2024

A novel visible-light promoted metal-free radical cascade cyclization reaction has been developed with 3-allyl-2-arylquinazolinones as a new class of acceptor. This photocatalytic protocol represents an efficient approach to construct phosphorylated dihydroisoquinolino[1,2-

Language: Английский

Citations

1

Photoredox/HAT-Catalyzed Intramolecular Hydrocyclization of Alkenes toward 2,3-Fused Quinazolinones and Dihydroquinazolinones DOI
Dong Li,

Xiaoqing Wang,

Yanhui Gou

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 2, 2024

New photochemical approaches to 2,3-fused quinazolinones and dihydroquinazolinones are disclosed. The intramolecular hydrocyclization proceeds in moderate excellent yields across diverse alkenes with high regioselectivity diastereocontrol. Mechanistic studies indicated that the radical cascade processes involve thiophenol acting as single-electron transfer hydrogen atom reagents. success of gram-scale synthesis proves strategy can be used for practical applications.

Language: Английский

Citations

1

TfOH-Promoted Decyanative Cyclization toward the Synthesis of 2,1-Benzisoxazoles DOI
Mengge Zhang, Yonggang Meng,

Yangang Wu

et al.

The Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 86(11), P. 7326 - 7332

Published: May 20, 2021

A novel solvent-free, TfOH-promoted decyanative cyclization approach for the synthesis of 2,1-benzisoxazoles has been developed. The reactions are complete instantly at room temperature and result in formation desired a 34–97% isolated yield.

Language: Английский

Citations

9

C1‐Functionalization of 1,2,3,4‐Tetrahydroisoquinolines (THIQs) DOI
Zahra Tashrifi,

Mohammad Mohammadi Khanaposhtani,

Bagher Larijani

et al.

Asian Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 10(10), P. 2421 - 2439

Published: Aug. 30, 2021

Abstract 1,2,3,4‐tetrahydroisoquinoline (THIQ) and its derivatives possess a widespread biochemical, pharmaceutical biological properties they are the key building blocks in structure of drugs natural alkaloids. Accordingly, construction multi‐substituted polycyclic THIQs through functionalization at different positions especially C1‐position have come to center attraction recent studies. In this review, we've focused on classification C1‐functionalization research articles from 2013 on, including brief description reaction mechanisms for synthesis based type substituents 1‐position THIQ moiety. From point view, main categories C1‐Functionalization with annulation.

Language: Английский

Citations

8

Acid-Promoted Redox-Annulation toward 1,2-Disubstituted-5,6-dihydropyrrolo[2,1-α]isoquinolines: Synthesis of the Lamellarin Core DOI Creative Commons

Guo-Quan Hou,

Wenyan Zhao, Changjiang Deng

et al.

ACS Omega, Journal Year: 2022, Volume and Issue: 7(42), P. 37050 - 37060

Published: Oct. 14, 2022

An efficient synthesis of a variety 1,2-disubstituted-5,6-dihydropyrrolo[2,1-α]isoquinoline derivatives via an acid-promoted cyclization reaction between 1,2,3,4-tetrahydroisoquinoline (THIQ) and substituted α,β-unsaturated aldehyde is reported. This cycloaddition allows access to structurally diverse multisubstituted dihydropyrrolo[2,1-α]isoquinolines in moderate good yields, which was the core scaffold marine natural alkaloid lamellarins.

Language: Английский

Citations

6