TBHP/KI-Promoted Oxidative Cyclization of α-Aminoketones for One-Pot Synthesis of Substituted 2-Acyloxazoles DOI

Jiecheng Zheng,

Dali Zhu,

Lin Gan

et al.

Synthesis, Journal Year: 2022, Volume and Issue: 55(09), P. 1419 - 1426

Published: Dec. 12, 2022

Abstract A metal-free and facile synthesis of substituted 2-acyloxazole derivatives from α-aminoketones was developed via a TBHP/KI-promoted oxidative cyclization. This procedure proceeded smoothly under mild conditions broad scope 2-acyloxazoles were obtained in moderate to good yields.

Language: Английский

Recent advances in iodine–DMSO mediated C(sp3)–H functionalization of methyl-azaarenes via Kornblum oxidation DOI
Swadhin Swaraj Acharya,

Sagarika Patra,

Liza Mama Barad

et al.

New Journal of Chemistry, Journal Year: 2024, Volume and Issue: 48(17), P. 7614 - 7638

Published: Jan. 1, 2024

In the iodine–DMSO medium, methyl group of azaarenes is converted into aldehyde via Kornblum oxidation and trapped in situ by nucleophiles to create azaarene-linked functionalized scaffolds.

Language: Английский

Citations

7
FeCl3/KI‐Catalyzed Tandem Oxidative Cyclization for Switchable Total Synthesis of Luotonin A, B and Derivatives DOI

Song Yingchun,

Ming‐Xuan Wang,

Yun‐Ying Yi

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(6), P. 1348 - 1355

Published: Jan. 13, 2024

Abstract A total synthesis strategy was developed for the of luotonin A, B and their analogues using synergistic FeCl 3 /KI‐catalyzed oxidative cyclization. This protocol utilizes cheap widely available N ‐propargyl 2‐methyl‐quinazolinones arylamines under mild conditions, it has a wide substrate scope high atom economy. Different natural products (luotonin derivatives) can be synthesized via unique switchable approach. Further transformations from to E structural modification demonstrate potential applications this method. Moreover, camptothecin also modified with reported afford hydroxyl‐substituted product.

Language: Английский

Citations

4
PIFA-mediated room temperature dehydrogenative annulation for the synthesis of 2-alkenyl oxazoles DOI
Kang Chen, Jie‐Ping Wan,

Liyun Zhou

et al.

Journal of Molecular Structure, Journal Year: 2024, Volume and Issue: 1308, P. 138142 - 138142

Published: March 24, 2024

Language: Английский

Citations

3
Oxytrofalcatin Puzzle: Total Synthesis and Structural Revision of Oxytrofalcatins B and C DOI
Kazuma Sugitate, Toshiki Yamashiro,

Ibuki Takahashi

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(14), P. 9920 - 9926

Published: July 11, 2023

The previously reported structures of oxytrofalcatins B and C possess a benzoyl indole core. However, following synthesis NMR comparison both the proposed structure synthesized oxazole, we have revised as oxazoles. synthetic route developed herein can further our understanding biosynthetic pathways that govern production natural 2,5-diaryloxazoles.

Language: Английский

Citations

3
Halogen cation-promoted and solvent-regulated electrophilic cyclization for the regioselective synthesis of 3-haloquinolines and 3-halospirocyclohexadienones DOI
Jianming Li, Chengxiao Liu, Zihan Zhao

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(11), P. 2440 - 2446

Published: Jan. 1, 2023

A novel approach for the production of halogen cations through reaction halogens with silver ions is described in this paper. On basis, regioselective synthesis 3-haloquinolines and 3-halospirocyclohexadienones realized solvent regulation. The gram-scale compatibility complex substrates demonstrate synthetic potential protocol, which will be an appealing strategy organic synthesis.

Language: Английский

Citations

0
TBHP/KI-Promoted Oxidative Cyclization of α-Aminoketones for One-Pot Synthesis of Substituted 2-Acyloxazoles DOI

Jiecheng Zheng,

Dali Zhu,

Lin Gan

et al.

Synthesis, Journal Year: 2022, Volume and Issue: 55(09), P. 1419 - 1426

Published: Dec. 12, 2022

Abstract A metal-free and facile synthesis of substituted 2-acyloxazole derivatives from α-aminoketones was developed via a TBHP/KI-promoted oxidative cyclization. This procedure proceeded smoothly under mild conditions broad scope 2-acyloxazoles were obtained in moderate to good yields.

Language: Английский

Citations

0