Improvements in 1,3-dipolar cycloaddition of nitrones to fluorinated dipolarophiles under solvent-free microwave activation

被引：30

作者：

Loupy, A ^{[1
]}

Petit, A ^{[1
]}

BonnetDelpon, D ^{[1
]}

机构：

[1] CTR ETUD PHARMACEUT,BIOCIS,SYNTH ORGAN LAB,CNRS,F-92296 CHATENAY MALABRY,FRANCE

来源：

JOURNAL OF FLUORINE CHEMISTRY | 1995年 / 75卷 / 02期

关键词：

dipolar cycloaddition; nitrones; fluorinated dipolarophiles; microwave activation; solvent-free conditions;

D O I：

10.1016/0022-1139(95)03330-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

1,3-Dipolar cycloadditions between ethyl trifluoracetoacetate or alpha-trifluoromethylstyrene and N-(benzylidene) methylamine N-oxide were performed in the absence of solvent. Under microwave irradiation in a monomode Maxidigest Prolabo reactor, quantitative yields were obtained within 3 min. Compared to conventional heating under the same conditions, the yields are significantly increased (from 55%-64% to 88.98%). Classical conditions using boiling toluene (65% within 24-48 h) are now considerably improved.

引用

页码：215 / 216

页数：2

共 50 条

[11] An efficient and diastereoselective intramolecular 1,3-dipolar cycloaddition of cyclic azomethine ylides and nitrones
Pedrosa, Rafael
Andres, Celia
Nieto, Javier
Perez-Cuadrado, Cristobal
San Francisco, Ivan
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (14) : 3259 - 3265
[12] Synthesis of some new isoxazolidines by 1,3-dipolar cycloaddition reaction of nitrones and olefins
Mobinikhaledi, A
Foroughifar, N
Kalate, Z
TURKISH JOURNAL OF CHEMISTRY, 2005, 29 (02) : 147 - 152
[13] Nickel(II)-Catalyzed Enantioselective 1,3-Dipolar Cycloaddition of Nitrones with α,β-Unsaturated Acylcarboxylates
Xie, Lei
Yu, Xuan
Li, Jiaqi
Zhang, Zhenhua
Qin, Zhaohai
Fu, Bin
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (03) : 657 - 661
[14] Tricyclic-isoxazolidine analogues via intramolecular 1,3-dipolar cycloaddition reactions of nitrones
Saubern, Simon
Macdonald, James M.
Ryan, John H.
Woodgate, Ruth C. J.
Louie, Theola S.
Fuchter, Matthew J.
White, Jonathan M.
Holmes, Andrew B.
TETRAHEDRON, 2010, 66 (14) : 2761 - 2767
[15] Asymmetric 1,3-dipolar cycloaddition of chiral α,β-unsaturated-γ-sultams with nitrile oxides and nitrones
Zhang, H
Chan, WH
Lee, AWM
Xia, PF
Wong, WY
LETTERS IN ORGANIC CHEMISTRY, 2004, 1 (01) : 63 - 66
[16] Synthesis of iminosugars via 1,3-dipolar cycloaddition reactions of nitrones to α,β-unsaturated sugar aldonolactones
Stecko, Sebastian
Jurczak, Margarita
Panfil, Irma
Furman, Bartlomiej
Grzeszczyk, Barbara
Chmielewski, Marek
COMPTES RENDUS CHIMIE, 2011, 14 (01) : 102 - 125
[17] Cu(II)-catalyzed enantioselective 1,3-dipolar cycloaddition of nitrones with α, β-unsaturated acyl phosphonates
Xie, Lei
Bai, Hui
Li, Jiaqi
Yu, Xuan
Zhang, Zhenhua
Fu, Bin
TETRAHEDRON, 2017, 73 (20) : 2923 - 2930
[18] 1,3-Dipolar Cycloaddition of Nitrones with 5-Methylenehydantoins: Synthesis and Transformation of New Spirohydantoin Derivatives
Bahy, Amira
Kacem, Yakdhane
Ben Hassine, Bechir
SYNTHETIC COMMUNICATIONS, 2010, 40 (09) : 1377 - 1390
[19] Copper(I)-Catalyzed Asymmetric 1,3-Dipolar [3+4]Cycloaddition of Nitrones with Azoalkenes
Wei, Liang
Yao, Lu
Wang, Zuo-Fei
Li, Hua
Tao, Hai-Yan
Wang, Chun-Jiang
ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (23) : 3748 - 3752
[20] Intramolecular 1,3-dipolar cycloaddition of N-alkenyl nitrones en route to glycosyl piperidines
Marca, Eduardo
Delso, Ignacio
Tejero, Tomas
Vazquez, Jesus T.
Dorta, Rosa L.
Merino, Pedro
TETRAHEDRON LETTERS, 2009, 50 (51) : 7152 - 7155

← 1 2 3 4 5 →