Tandem epoxide or aziridine ring opening by azide/copper catalyzed [3+2] cycloaddition:: Efficient synthesis of 1,2,3-triazolo β-hydroxy or β-tosylamino functionality motif

被引：81

作者：

Kumaraswamy, Gullapalli ^{[1
]}

Ankamma, Kukkadapu ^{[1
]}

Pitchaiah, Arigala ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Div Organ Chem 3, Fine Chem Lab, Hyderabad 500007, Andhra Pradesh, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 25期

关键词：

D O I：

10.1021/jo701724f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[Graphics] A novel and practical procedure for the synthesis of small molecules possessing beta-hydroxy or N-tosylamino 1,2,3-triazole motif by azidation of epoxides or N-tosylaziridines with sodium azide followed by "click reaction" using eco-friendly PEG-400 as a reaction medium in the presence of 5 mol % of CuI is described. Enantiomerically pure epoxide and N-tosylaziridines were afforded in high yield with excellent ee values maintaining complete stereospecificity.

引用

页码：9822 / 9825

页数：4

共 50 条

[21] Efficient Pd(0)-catalyzed synthesis of 1,2,3-triazolo-3′-deoxycarbanucleosides and their analogues
Joubert, N
Schinazi, RF
Agrofoglio, LA
TETRAHEDRON, 2005, 61 (49) : 11744 - 11750
[22] Synthesis of hybrid 1,2,3-triazolo-δ-lactams/lactones using Huisgen [3+2] cycloaddition 'click-chemistry' in water
Kumar, Indresh
Rana, Sravendra
Cho, Jae Whan
Rode, Chandrashekhar V.
TETRAHEDRON-ASYMMETRY, 2010, 21 (03) : 352 - 355
[23] Copper-catalyzed synthesis of 5-substituted 1H-tetrazoles via the [3+2] cycloaddition of nitriles and trimethylsilyl azide
Jin, Tienan
Kitahara, Fukuzou
Kamijo, Shin
Yamamoto, Yoshinori
TETRAHEDRON LETTERS, 2008, 49 (17) : 2824 - 2827
[24] Synthesis and characterization of click-decahydrodecaborate derivatives by the copper(I) catalyzed [3+2] azide-alkyne cycloaddition reaction
El Anwar, Suzan
Laila, Zahra
Ramsubhag, Ron
Tlais, Sami
Safa, Ali
Dudley, Gregory
Naoufal, Daoud
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2018, 865 : 89 - 94
[25] The [3+2] cycloaddition route to 5-carbomethoxy-4H-1,2,3-triazolo[1,5-a][1]benzazepines from Baylis-Hillman acetates of 2-azidobenzaldehydes
Song, Young Seok
Lee, Kee-Jung
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2006, 43 (06) : 1721 - 1724
[26] Synthesis of highly diversified 1,2,3-triazole derivatives via domino [3+2] azide cycloaddition and denitration reaction sequence
Bakthadoss, Manickam
Sivakumar, Nagappan
Devaraj, Anthonisamy
Kumar, Polu Vijay
RSC ADVANCES, 2015, 5 (113) : 93447 - 93451
[27] A rapid efficient microwave-assisted synthesis of a 3′,5′-pentathymidine by copper(I)-catalyzed [3+2] cycloaddition
Lucas, Romain
Zerrouki, Rachida
Granet, Robert
Krausz, Pierre
Champavier, Yves
TETRAHEDRON, 2008, 64 (23) : 5467 - 5471
[28] SYNTHESIS AND REACTIVITY OF 1,2,3-TRIAZOLO[3,4-ALPHA]PYRIMIDINE RING SYSTEM . A NEW ROUTE TO 2-SUBSTITUTED PYRIMIDINES
SUTHERLAND, DR
TENNANT, G
JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1969, (18): : 1070 - +
[29] Amine-Catalyzed [3+2] Huisgen Cycloaddition Strategy for the Efficient Assembly of Highly Substituted 1,2,3-Triazoles
Wang, Lei
Peng, Shiyong
Danence, Lee Jin Tu
Gao, Yaojun
Wang, Jian
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (19) : 6088 - 6093
[30] Copper-catalyzed cross-coupling and sequential allene-mediated cyclization for the synthesis of 1,2,3-triazolo[1,5-a]quinolines
Yang, Jianhua
Xiong, Shaoqi
Ren, Yongsheng
Xiao, Tiebo
Jiang, Yubo
ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (36) : 7174 - 7182

← 1 2 3 4 5 →