Synthesis of Oxazoles Containing CF3-Substituted Alcohol Unit via Tandem Cycloisomerization/Hydroxyalkylation from N-Propargylamides with Trifluoropyruvates DOI Creative Commons
Juanjuan Gao,

Longhui Wu,

Shuqin Yu

и другие.

Molecules, Год журнала: 2024, Номер 29(24), С. 5848 - 5848

Опубликована: Дек. 11, 2024

Oxazoles are important five-membered heterocycles that contain both nitrogen and oxygen atoms. Due to their wide range of biological activities, many oxazoles demonstrate potential for extensive application in various fields, including medicinal chemistry. Trifluoromethyl carbinol, an pharmacophore, contains trifluoromethyl hydroxyl groups is common molecules with activities. Constructing a carbinol unit undoubtedly valuable expanding the chemical space drug discovery. In this study, simple efficient method was developed synthesis containing CF3-substituted alcohol via tandem cycloisomerization/hydroxyalkylation N-propargylamides trifluoropyruvates through rational Lewis acid catalytic mechanism. This Zn(OTf)2-catalyzed synthetic protocol operationally provides series moderate good yields. The demonstrates broad substrate scope, high functional group tolerance, atom economy can achieve gram-level reactions, indicating strong possibility its practical application.

Язык: Английский

Recent Advances in Visible Light-Induced C-H Functionalization of Imidazo[1,2-a]pyridines DOI Creative Commons
Juanjuan Gao,

Xinlei Fu,

Kai Yang

и другие.

Molecules, Год журнала: 2025, Номер 30(3), С. 607 - 607

Опубликована: Янв. 30, 2025

The imidazo[1,2-a]pyridine skeleton is widely present in many natural products and pharmaceutical agents. Due to its impressive significant biological activities, such as analgesic, anti-tumor, antiosteoporosis, anxiolytic properties, the derivatization of has attracted widespread attention from chemists. In recent years, progress been made imidazo[1,2-a]pyridines through direct C-H functionalization, especially visible light induction. This review highlights advances light-induced functionalization during past ten some reaction mechanisms are also discussed.

Язык: Английский

Процитировано

0
Hydrogen-Bonding Assisted Catalytic 1,2-Addition Reaction of Trifluoropyruvate with 2,4-Dihydrocylopenta[b]indoles DOI
K. Sandy Pang, Xin Li, Man Wang

и другие.

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Апрель 15, 2025

CF3-substituted tertiary alcohols are valuable as biologically active compounds, but the synthesis of corresponding cyclopentadiene derivatives remains challenging. The DABCO-catalyzed 1,2-addition reaction trifluoropyruvates with 2,4-dihydrocyclopenta[b]indoles has been developed, affording in up to 90% yield and >99:1 dr. catalytic is facilitated by hydrogen bonding (N-H···N) between cyclic amine indole moiety. Additionally, Et3N (1.0 equiv) can promote retro-1,2-addition CF3-subsituted alcohols, yielding dihydrocyclopenta[b]indole 1 72% yield.

Язык: Английский

Процитировано

0
Synthesis of Oxazoles Containing CF3-Substituted Alcohol Unit via Tandem Cycloisomerization/Hydroxyalkylation from N-Propargylamides with Trifluoropyruvates DOI Creative Commons
Juanjuan Gao,

Longhui Wu,

Shuqin Yu

и другие.

Molecules, Год журнала: 2024, Номер 29(24), С. 5848 - 5848

Опубликована: Дек. 11, 2024

Oxazoles are important five-membered heterocycles that contain both nitrogen and oxygen atoms. Due to their wide range of biological activities, many oxazoles demonstrate potential for extensive application in various fields, including medicinal chemistry. Trifluoromethyl carbinol, an pharmacophore, contains trifluoromethyl hydroxyl groups is common molecules with activities. Constructing a carbinol unit undoubtedly valuable expanding the chemical space drug discovery. In this study, simple efficient method was developed synthesis containing CF3-substituted alcohol via tandem cycloisomerization/hydroxyalkylation N-propargylamides trifluoropyruvates through rational Lewis acid catalytic mechanism. This Zn(OTf)2-catalyzed synthetic protocol operationally provides series moderate good yields. The demonstrates broad substrate scope, high functional group tolerance, atom economy can achieve gram-level reactions, indicating strong possibility its practical application.

Язык: Английский

Процитировано

1