Synthesis of 2-trifluoromethylated 3-pyrrolines/pyrrolidines via [3+2] cycloaddition of azomethine ylides with the participation of 3,3,3-trifluoroalanine

被引：0

作者：

Liu, Qian ^{[1
]}

Yoshikawa, Isao ^{[1
]}

Kudo, Kazuaki ^{[1
]}

机构：

[1] Univ Tokyo, Inst Ind Sci, 4-6-1 Komaba,Meguro Ku, Tokyo 1538505, Japan

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2022年 / 264卷

关键词：

X=Y-ZH SYSTEMS; 1,3-DIPOLAR CYCLOADDITION; DECARBOXYLATIVE ROUTE; ENANTIOSELECTIVE CONSTRUCTION; ASYMMETRIC CONSTRUCTION; POTENTIAL 1,3-DIPOLES; PYRROLIDINES; MECHANISM; FRAMEWORK; PYRROLES;

D O I：

10.1016/j.jfluchem.2022.110061

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

2-Trifluoromethylated 3-pyrrolines and pyrrolidines were synthesized via condensation of 3,3,3-trifluoroalanine with carbonyl compounds, decarboxylative for-mation of azomethine ylides, and the subsequent [3+2] cycloaddition with electron deficient alkynes and alkenes. The reaction proceeded under mild conditions to give the adducts in moderate to good yields. The product 3-pyrroline was successfully converted to the corresponding pyrrole upon treatment with o-iodoxybenzoic acid.

引用

页数：8

共 50 条

[31] THERMOLYSIS OF 3-NITRO PYRROLIDINES - PREPARATION OF 3-PYRROLINES VIA HNO2 ELIMINATION
BENHAOUA, H
DANIONBOUGOT, R
CARRIE, R
[J]. BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE, 1989, (03): : 409 - 412
[32] Efficient synthesis of novel antiproliferative steroidal spirooxindoles via the [3+2] cycloaddition reactions of azomethine ylides
Yu, Bin
Sun, Xiao-Nan
Shi, Xiao-Jing
Qi, Ping-Ping
Zheng, Yi-Chao
Yu, De-Quan
Liu, Hong-Min
[J]. STEROIDS, 2015, 102 : 92 - 100
[33] A facile synthesis of glyco 3-nitrochromane hybrid pyrrolidinyl spiro heterocycles via [3+2] cycloaddition of azomethine ylides
Rao, J. Naga Siva
Raghunathan, R.
[J]. TETRAHEDRON LETTERS, 2015, 56 (17) : 2276 - 2279
[34] Silver-Catalyzed [3+2] Cycloaddition of Azomethine Ylides with Isocyanides for Imidazole Synthesis
Hu, Zhongyan
Dong, Jinhuan
Xu, Xianxiu
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (20) : 3585 - 3591
[35] Organocatalytic enantioselective [3+2]cycloaddition of azomethine ylides and α,β-unsaturated aldehydes
Vicario, Jose L.
Reboredo, Silvia
Badia, Dolores
Carrillo, Luisa
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (27) : 5168 - 5170
[36] SYNTHESIS OF THIOPHENYL SPIROOXINDOLOPYRROLIZIDINES VIA [3+2]-CYCLOADDITION OF AZOMETHINE YLIDE
Gurumurthi, S.
Sundari, V.
Valliappan, R.
[J]. INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2009, 19 (02) : 179 - 180
[37] Dearomative [3+2] cycloaddition reaction of nitrobenzothiophenes with nonstabilized azomethine ylides
Wang, Kai-Kai
Xie, Yan-Xin
Li, Yan-Li
Chen, Rongxiang
Wang, Zhan-Yong
[J]. RSC ADVANCES, 2020, 10 (48) : 28720 - 28724
[38] [3+2] Cycloaddition of Masked o-Benzoquinones with Azomethine Ylides
Chittimalla, Santhosh Kumar
Kuppusamy, Rajesh
Chakrabarti, Anjan
[J]. SYNLETT, 2012, (13) : 1901 - 1906
[39] A new trifluoromethylated sulfonamide phosphine ligand for Ag(I)-catalyzed enantioselective [3+2] cycloaddition of azomethine ylides
Wu, Yuanqi
Xu, Bing
Liu, Bing
Zhang, Zhan-Ming
Liu, Yu
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (06) : 1395 - 1401
[40] Organocatalytic enantioselective (3+2) cycloaddition using stable azomethine ylides
Fernandez, Naiara
Carrillo, Luisa
Vicario, Jose L.
Badia, Dolores
Reyes, Efraim
[J]. CHEMICAL COMMUNICATIONS, 2011, 47 (45) : 12313 - 12315

← 1 2 3 4 5 →