Ring-expansion reaction for the synthesis of 2-(trifluoromethyl)oxazoles and 3-(trifluoromethyl)-1,2,4-triazines

被引：6

作者：

Teng, Yun ^{[1
,2
]}

Fang, Tingyu ^{[1
,2
]}

Lin, Zitong ^{[3
]}

Qin, Lu ^{[3
]}

Jiang, Mengfan ^{[3
]}

Wu, Wei ^{[3
]}

You, Yi ^{[1
,2
]}

Weng, Zhiqiang ^{[1
,2
,3
]}

机构：

[1] Fuzhou Univ, Coll Chem, Key Lab Mol Synth & Funct Discovery, Fuzhou 350108, Peoples R China

[2] Fuzhou Univ, Coll Chem, Fujian Prov Key Lab Electrochem Energy Storage Mat, Fuzhou 350108, Peoples R China

[3] Minjiang Univ, Coll Mat & Chem Engn, Fujian Engn Res Ctr New Chinese Lacquer Mat, Fuzhou 350108, Peoples R China

来源：

TETRAHEDRON LETTERS | 2022年 / 107卷

关键词：

Trifluoroacetic anhydride; Trifluoromethyl; 1; 2; 4-Triazine; Oxazole; Ring-expansion reaction; OXAZOLE; CYCLIZATION; CHEMISTRY; TRIFLUOROMETHYLATION; DERIVATIVES; THIAZOLE; ACCESS; ACID;

D O I：

10.1016/j.tetlet.2022.154100

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A ring-expansion reaction of 2H-azirine with trifluoroacetic anhydride for the synthesis of 2-(trifluo-romethyl)oxazoles is disclosed. The reaction features readily available reactants, relatively mild condi-tions, and high yields of products. The generated 2-(trifluoromethyl)oxazole core could be easily converted into 3-(trifluoromethyl)-1,2,4-triazines through hydrazinolysis reaction.(c) 2022 Elsevier Ltd. All rights reserved.

引用

页数：6

共 48 条

[31] REACTIONS OF BETA-AZIDOSTYRENES WITH HALOGENOACETIC ACID - A NOVEL FORMATION OF OXAZOLES
TAKEUCHI, H
KITAMURA, Y
HAYAKAWA, S
KOYAMA, K
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (19) : 1414 - 1415
[32] Synthesis of Oxazole, Oxazoline and Isoxazoline Derived Marine Natural Products: A Review
Tilvi, Supriya
Singh, Keisham S.
[J]. CURRENT ORGANIC CHEMISTRY, 2016, 20 (08) : 898 - 929
[33] Aromatic Trifluoromethylation with Metal Complexes
Tomashenko, Olesya A.
Grushin, Vladimir V.
[J]. CHEMICAL REVIEWS, 2011, 111 (08) : 4475 - 4521
[34] OXAZOLE CHEMISTRY - A REVIEW OF RECENT ADVANCES
TURCHI, IJ
[J]. INDUSTRIAL & ENGINEERING CHEMISTRY PRODUCT RESEARCH AND DEVELOPMENT, 1981, 20 (01): : 32 - 76
[35] CHEMISTRY OF OXAZOLES
TURCHI, IJ
DEWAR, MJS
[J]. CHEMICAL REVIEWS, 1975, 75 (04) : 389 - 437
[36] Uneyama K., 2006, Organofluorine Chemistry
[37] Perfluorocarboxylic Anhydrides Triggered Cyclization: Access to 4-Perfluoroalkylpyridines
Wang, Zeng
You, Chenhui
Wang, Changfang
Weng, Zhiqiang
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (22) : 14926 - 14935
[38] Welch J.T., 1991, FLUORINE BIOORGANIC
[39] Recent advances in the synthesis of fluoroalkylated compounds using fluoroalkyl anhydrides
Wu, Wei
You, Yi
Weng, Zhiqiang
[J]. CHINESE CHEMICAL LETTERS, 2022, 33 (10) : 4517 - 4530
[40] Synthesis of polysubstituted 5-trifluoromethyl isoxazoles via denitrogenative cyclization of vinyl azides with trifluoroacetic anhydride
Wu, Wei
Chen, Qiaoling
Tian, Yishi
Xu, Yihui
Huang, Yangjie
You, Yi
Weng, Zhiqiang
[J]. ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (14): : 1878 - 1883

← 1 2 3 4 5 →