Visible-light-promoted cyclization of 3-indolylallylamides enabling synthesis of tetrahydrocarbolinones DOI Open Access

Jingrui He,

Chengting Wang,

Haibo Mei

и другие.

Tetrahedron, Год журнала: 2023, Номер 150, С. 133776 - 133776

Опубликована: Дек. 4, 2023

Язык: Английский

Electrocatalytic Annulation–Iodosulfonylation of Indole‐Tethered 1,6‐Enynes to Access Pyrrolo[1,2‐a]indoles DOI

Ya‐Yu Yuan,

Xi Chen,

J. Wang

и другие.

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(10)

Опубликована: Янв. 9, 2024

Abstract We present the first example of electrocatalytic three‐component annulation–iodosulfonylation indole‐tethered 1,6‐enynes with arylsulfonyl hydrazides and KI for accessing various iodosulfonated pyrrolo[1,2‐ a ]indoles in moderate to excellent yields high stereospecificity. This electrosynthesis opens new avenues construction skeleton good functional group compatibility under environmentally benign condition. Based on control experiments cyclic voltammetry data, we suggested plausible reaction mechanism which included anodic oxidation, homolysis iodide, radical addition, 5 ‐ exo dig cyclization, coupling or nucleophilic attack iodide ions cascade.

Язык: Английский

Процитировано

8
Visible-light-induced photocatalyst-free cascade cyclization of 3-(2-(ethynyl)phenyl)quinazolinones to sulfonated quinolino[2,1-b]quinazolinones DOI

Fan‐Lin Zeng,

Lili Wang,

Yuxin Luo

и другие.

Chemical Communications, Год журнала: 2024, Номер 60(56), С. 7228 - 7231

Опубликована: Янв. 1, 2024

A visible-light-induced K 2 S O 8 -promoted cascade sulfonation/cyclization reaction to afford a series of sulfonated quinolino[2,1- b ]quinazolinones has been developed under mild conditions.

Язык: Английский

Процитировано

4
Copper‐catalyzed radical‐induced annulation‐halo(bi)cyanomethylation of indole‐tethered 1,6‐enynes toward pyrrolo[1,2‐a]indoles DOI
Hang‐Dong Zuo,

Ya‐Yu Yuan,

Xi Chen

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(17), С. 3578 - 3584

Опубликована: Июнь 18, 2024

Abstract A copper‐catalyzed radical‐induced annulation‐halocyanomethylation of indole‐linked 1,6‐enynes has been established using haloacetonitrile as radical precursors, enabling the synthesis 21 cyanomethylated pyrrolo[1,2‐ a ]indoles with yields ranging from 42% to 81% and Z / E ratio up 19:1. Moreover, by adjusting reaction temperature, variation annulation‐bromobicyanomethylation process was achieved, resulting in production 12 bicyanomethylated ]indole isomers 41–68%. The stereoisomeric mixture products could be purified their pure configurations through recrystallization. proposed mechanism formulated series control experiments.

Язык: Английский

Процитировано

4
Metal-free polychloromethylation/cyclization of unactivated alkenes towards ring-fused tricyclic indolones and benzoimidazoles DOI

Yechun Wu,

Han Liu,

Lingli Liu

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(35), С. 7079 - 7084

Опубликована: Янв. 1, 2023

Polychloromethylative cyclization of N-alkenyl indoles was developed under metal-free conditions to afford tricyclic pyridoindolones and pyrroloindolones in moderate good yields. In the reaction, commercially available CHCl3 CH2Cl2 were employed as tri- dichloromethyl radical sources. Moreover, dichloromethylated polycyclic benzoimidazoles can also be obtained standard conditions.

Язык: Английский

Процитировано

9
Accessing pyrrolo[1,2-a]indole derivatives via visible-light-induced dearomatizative cyclization of indoles DOI
Zhao‐Sheng Liu, Xiaochen Ji,

Lilan Duan

и другие.

Chemical Communications, Год журнала: 2024, Номер 60(37), С. 4902 - 4905

Опубликована: Янв. 1, 2024

Dearomatizative cyclization of indoles: a novel synthetic method for pyrrolo[1,2- ]indole derivatives through visible-light-induced cascade dearomatizative indoles with external nucleophiles has been developed.

Язык: Английский

Процитировано

3
Visible-light-induced trifluoromethylation/cyclization of unactivated alkenes: Synthesis of CF3-substituted fused tricyclic indoles DOI

Jialong Jiao,

Yang Geng, Shanshan Zhang

и другие.

Tetrahedron Letters, Год журнала: 2024, Номер 147, С. 155218 - 155218

Опубликована: Июль 27, 2024

Язык: Английский

Процитировано

3
Photo‐Induced Difluoromethylation‐Cyclization of Indoles Using Tetrazole Sulfone Reagent Under Visible Light DOI

Yuping Zhu,

Yongsheng Huang,

Xuan‐Yu Zhou

и другие.

ChemistrySelect, Год журнала: 2024, Номер 9(24)

Опубликована: Июнь 24, 2024

Abstract Polycyclic indoles are prevailed in natural products, pharmaceuticals and biologically active compounds. Herein is described photo‐induced difluoromethylation‐cyclization of N ‐alkene tethered to synthesis tetrahydropyrido[1,2‐ a ]indole using 5‐((difluoromethyl)sulfonyl)‐1‐phenyl‐1H‐tetrazole as CF 2 H radical source. This photochemical reaction tolerates an array functional groups like ester, cyano, ketone, halide, ether, aldehyde heteocycles. Mechanistic experiments indicated that the difluoromethyl single electron transfer were involved.

Язык: Английский

Процитировано

2
Transition-Metal Free Approaches to Access N-Heterocycles and Valuable Intermediates from Aryldiazonium Salts DOI
Mani Ramanathan, Ziad Moussa

Organic Chemistry Frontiers, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 13, 2024

Development of novel and efficient synthetic methods to achieve valuable N-heterocycles from aryldiazonium salts has been an important research area in organic chemistry for several decades.

Язык: Английский

Процитировано

1
Visible-light-promoted cyclization of 3-indolylallylamides enabling synthesis of tetrahydrocarbolinones DOI Open Access

Jingrui He,

Chengting Wang,

Haibo Mei

и другие.

Tetrahedron, Год журнала: 2023, Номер 150, С. 133776 - 133776

Опубликована: Дек. 4, 2023

Язык: Английский

Процитировано

3