Catalyst-Free Cascade Annulation of Enaminones and Aryl Diazonium Tetrafluoroboronates for Cinnoline Synthesis and the Anti-Inflammatory Activity Study DOI

Shanghui Tian,

Yunyun Liu, Changfeng Wan

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(4), С. 2433 - 2442

Опубликована: Фев. 8, 2023

A simple and concise method for the synthesis of cinnolines has been developed by reactions readily available enaminones aryl diazonium tetrafluoroboronates. The run efficiently to provide with broad diversity in substructure heating dimethyl sulfoxide without using any catalyst or additive. In addition, primary investigation anti-inflammatory activity these products leads observation p-chlorobenzoyl (3f) p-nitrobenzoyl (3j) as attractive compounds vitro.

Язык: Английский

I2-DMSO-Mediated Construction of 2,3- and 2,4-Disubstituted Pyrimido[1,2-b]indazole Skeletons DOI
Linlin Ma, You Zhou,

Yong‐Xing Tang

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(6), С. 3941 - 3953

Опубликована: Фев. 29, 2024

An efficient synthetic method for constructing 2,3- and 2,4-disubstituted pyrimidio[1,2-b]indazole skeletons through I2-DMSO-mediated substrate-controlled regioselective [4 + 2] cyclization is reported. The reaction conditions are mild, its operation simple, the substrate scope wide. More than 60 derivatives have been synthesized, providing a new methodology related molecules potentially enriching bioactive-molecule libraries.

Язык: Английский

Процитировано

6

Visible-Light-Initiated Difunctionalization of Quinoxalin-2(1H)-ones with Acyloxy Nitroso Compounds DOI

Runye Gao,

Fang Wang, Xiao Geng

и другие.

Organic Letters, Год журнала: 2022, Номер 24(39), С. 7118 - 7122

Опубликована: Сен. 25, 2022

Herein, a photoinitiated radical relay reaction of quinoxalin-2(1H)-ones, with acyloxy nitroso compounds as source radicals, is described. Although the C-H functionalization quinoxalin-2(1H)-ones has been investigated, its difunctionalization, simultaneous construction C-C and N-N bonds directly via reaction, rarely reported. Moreover, obtained products underwent sequential reactions to access C7-NO2 under mild conditions.

Язык: Английский

Процитировано

25

Thiazole-5-carbaldehyde Synthesis by Cascade Annulation of Enaminones and KSCN with Dess–Martin Periodinane Reagent DOI
Kang Chen,

Baoli Zhao,

Yunyun Liu

и другие.

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(21), С. 14957 - 14964

Опубликована: Окт. 19, 2022

The Dess-Martin periodinane (DMP) reagent-mediated reactions of tertiary enaminones with potassium thiocyanate for the synthesis thiazole-5-carbaldehydes are developed. product formation involves cascade hydroxyl thiocyanation C═C double bond, intramolecular hydroamination C≡N and thiazole annulation by condensation on ketone carbonyl site, representing novel reaction pathways in between salt. DMP plays dual roles mediating free radical inducing unconventional selective thiazole-5-carbaldehyde masking situ generated formyl group during process.

Язык: Английский

Процитировано

25

Photoinduced Three‐Component Cyclization of Arylamines, Enaminones and Difluorobromoacetates to 2,3‐Difunctionalized Quinolines DOI
Jie Huo, Xiao Geng, Wanmei Li

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2022, Номер 364(20), С. 3539 - 3543

Опубликована: Авг. 26, 2022

Abstract A photoinduced multicomponent reaction of arylamines, enaminones and difluorobromoacetates for the synthesis 2,3‐difunctionalized quinolines is reported. This strategy features broad functional groups tolerance wide substrate scopes that enables further synthetic applications obtained products. Mechanistic studies reveal intermolecular [3+3] cyclization between in‐situ generated 1,3‐vinylimine ions arylamines key step in this transformation. magnified image

Язык: Английский

Процитировано

23

Catalyst-Free Cascade Annulation of Enaminones and Aryl Diazonium Tetrafluoroboronates for Cinnoline Synthesis and the Anti-Inflammatory Activity Study DOI

Shanghui Tian,

Yunyun Liu, Changfeng Wan

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(4), С. 2433 - 2442

Опубликована: Фев. 8, 2023

A simple and concise method for the synthesis of cinnolines has been developed by reactions readily available enaminones aryl diazonium tetrafluoroboronates. The run efficiently to provide with broad diversity in substructure heating dimethyl sulfoxide without using any catalyst or additive. In addition, primary investigation anti-inflammatory activity these products leads observation p-chlorobenzoyl (3f) p-nitrobenzoyl (3j) as attractive compounds vitro.

Язык: Английский

Процитировано

13