Cycloaddition Reactions of Azides and Electron-Deficient Alkenes in Deep Eutectic Solvents: Pyrazolines, Aziridines and Other Surprises

被引：16

作者：

Sebest, Filip ^{[1
]}

Lachhani, Kushal ^{[1
]}

Pimpasri, Chaleena ^{[1
]}

Casarrubios, Luis ^{[1
,2
,3
]}

White, Andrew J. P. ^{[1
]}

Rzepa, Henry S. ^{[1
]}

Diez-Gonzalez, Silvia ^{[1
]}

机构：

[1] Imperial Coll London, Dept Chem, MSRH, White City Campus,80 Wood Lane, London W12 0BZ, England

[2] Univ Complutense, Fac Ciencias Quim, Dept Quim Organ 1, E-28040 Madrid, Spain

[3] Ctr Innovac Quim Avanzada ORFEO CINQA, Madrid 28040, Spain

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2020年 / 362卷 / 09期

基金：

英国工程与自然科学研究理事会;

关键词：

Alkenes; Azides; Cycloaddition; Heterocycles; Solvent Effects; 1,3-DIPOLAR CYCLOADDITION; EFFICIENT CATALYST; CRYSTAL-STRUCTURE; ARYL AZIDES; CHEMISTRY; ACID; DELTA-2-1,2,3-TRIAZOLINES; HYDRAZINE; CUAAC;

D O I：

10.1002/adsc.201901614

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The reaction of organic azides and electron-deficient alkenes was investigated in a deep eutectic solvents. A series of highly substituted 2-pyrazolines was successfully isolated and their formation rationalised by DFT calculations. The critical effect of substitution was also explored; even relatively small changes in the cycloaddition partners led to completely different reaction outcomes and triazolines, triazoles or enaminones can be formed as major products depending on the alkene employed.

引用

页码：1877 / 1886

页数：10

共 20 条

[1] Pauson-Khand reactions of electron-deficient alkenes
Rivero, MR
Adrio, J
Carretero, JC
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2002, 2002 (17) : 2881 - 2889
[2] Diastereoselectivity in 1,3-dipolar cycloaddition reactions between indolic nitrones and electron-deficient alkenes
Greci, L
Tommasi, G
Bruni, P
Sgarabotto, P
Righi, L
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2001, 2001 (16) : 3147 - 3153
[3] PhI(OAc) 2 -Promoted Regioselective Cycloaddition of N -Aminopyridinium Ylides with Electron-Deficient Alkenes
Wang, Junlei
Chen, Guiling
Shi, Chengcheng
Xie, Qinglin
Gao, Guocheng
Li, Yanan
Du, Haijun
Cai, Xiaohua
Li, Hongqing
Huang, Binbin
SYNLETT, 2024, 35 (13) : 1551 - 1556
[4] Synthesis of CF2H-Substituted Pyrazolines by [3+2] Cycloaddition between CF2HCHN2 and Electron-Deficient Alkenes
Li, Jue
Yu, Xin-Ling
Cossy, Janine
Lv, Song-Yang
Zhang, Hai-Long
Su, Fu
Mykhailiuk, Pavel K.
Wu, Yong
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (02) : 266 - 270
[5] Synthesis of spiro[indoline-3,3′-pyrrolizines] by 1,3-dipolar reactions between isatins, L-proline and electron-deficient alkenes
Quiroga, Jairo
Romo, Pablo
Cobo, Justo
Glidewell, Christopher
ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2017, 73 : 1109 - +
[6] Alkenylborane-Derived Frustrated Lewis Pairs: Metal-Free Catalytic Hydrogenation Reactions of Electron-Deficient Alkenes
Reddy, J. Sreedhar
Xu, Bao-Hua
Mahdi, Tayseer
Froehlich, Roland
Kehr, Gerald
Stephan, Douglas W.
Erker, Gerhard
ORGANOMETALLICS, 2012, 31 (15) : 5638 - 5649
[7] Phosphine-Catalyzed [3+2] Cycloaddition Reactions of Azomethine Imines with Electron-Deficient Alkenes: A Facile Access to Dinitrogen-Fused Heterocycles
Li, Zhen
Yu, Hao
Liu, Honglei
Zhang, Lei
Jiang, Hui
Wang, Bo
Guo, Hongchao
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (06) : 1731 - 1736
[8] Regio- and diastereoselectivity in 1,3-dipolar cycloaddition reactions of 2-phenylisatogen and its 3-phenylimino derivative with electron-deficient alkenes
Astolfi, P
Bruni, P
Greci, L
Stipa, P
Righi, L
Rizzoli, C
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (14) : 2626 - 2634
[9] Recent Progress of Cu-Catalyzed Azide-Alkyne Cycloaddition Reactions (CuAAC) in Sustainable Solvents: Glycerol, Deep Eutectic Solvents, and Aqueous Media
Nebra, Noel
Garcia-Alvarez, Joaquin
MOLECULES, 2020, 25 (09):
[10] Thermal azide-alkene cycloaddition reactions: straightforward multi-gram access to 2-1,2,3-triazolines in deep eutectic solvents
Sebest, Filip
Casarrubios, Luis
Rzepa, Henry S.
White, Andrew J. P.
Diez-Gonzalez, Silvia
GREEN CHEMISTRY, 2018, 20 (17) : 4023 - 4035

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