A Fresh Look at the Staudinger Reaction on Azido Esters: Formation of 2H-1,2,3-Triazol-4-ols from α-Azido Esters Using Trialkyl Phosphines

被引：15

作者：

Taylor, Scott D. ^{[1
]}

Lohani, Chuda Raj ^{[1
]}

机构：

[1] Univ Waterloo, Dept Chem, 200 Univ Ave West, Waterloo, ON N2L 3G1, Canada

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 17期

基金：

加拿大自然科学与工程研究理事会;

关键词：

SOLID-PHASE SYNTHESIS; TERTIARY PHOSPHINES; DERIVATIVES; PHOSPHAZIDE; DAPTOMYCIN; ANALOGS; CHEMISTRY; STRATEGY; ACIDS;

D O I：

10.1021/acs.orglett.6b02204

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Phenyl esters of alpha-azido acids react with trialkylphosphines in THF/H2O to give 5-substituted 2H-1,2,3-triazol-4-ols in good to excellent yields. In contrast, their reaction with PPh3 in THF/H2O give the amino esters as the major product and no triazoles. Reaction between an alpha-azido phenyl ester and P(OEt)(3) provided the corresponding phosphoramidate in excellent yield, but no triazole was formed.

引用

页码：4412 / 4415

页数：4

共 7 条

[1] Synthesis of 2-(1H-1,2,3-Triazol-1-yl)-1,4-naphthoquinones from 2-Azido-1,4-naphthoquinone and Terminal Alkynes
do Nascimento, Wilson Silva
Camara, Celso Amorim
de Oliveira, Ronaldo Nascimento
SYNTHESIS-STUTTGART, 2011, (20): : 3220 - 3224
[2] Synthesis, Antimicrobial Activity, Molecular Docking and DFT Study: Aryl-Carbamic Acid 1-Benzyl-1H-[1,2,3]Triazol-4-ylmethyl Esters
Naveen
Kumar Tittal, Ram
Vikas, Ghule D.
Rani, Poonam
Lal, Kashmiri
Kumar, Ashwani
CHEMISTRYSELECT, 2020, 5 (22): : 6723 - 6729
[3] Formation of 4-(het)aryl-3H-1,5-benzodiazepine-2-carboxylates from (het)aroylpyruvate esters and o-phenylenediamine
Khramtsova, Ekaterina E.
Dmitriev, Maksim V.
Maslivets, Andrey N.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2023, 59 (08) : 574 - 579
[4] Synthesis of Novel Substituted 4-[1-(1-Phenyl-1H-[1,2,3]triazol-4-yl-methyl)-1H-benzimidazol-2-yl]piperidine-1-carboxylic Acids tert-Butyl Esters. Evaluation of Cytotoxic and Antimicrobial Activity
Naresh, P.
Hemasri, Y.
Limbadri, P.
Rao, Y. Jayaprakash
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2025, 95 (03) : 538 - 547
[5] Copper-Mediated Synthesis of (E)-1-Azido and (Z)-1,2-Diazido Alkenes from 1-Alkene-1,2-diboronic Esters: An Approach to Mono-and 1,2-Di-(1,2,3-Triazolyl)-Alkenes and Fused Bis-(1,2,3-Triazolo)-Pyrazines
Mali, Maruti
Jayaram, Vankudoth
Sharma, Gangavaram V. M.
Ghosh, Subhash
Berree, Fabienne
Dorcet, Vincent
Carboni, Bertrand
JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (23) : 15104 - 15115
[6] Synthesis of 3-aryl-4(3H)-quinazolinones from anthranilic acid, ortho esters, and anilines using Ce(CH3SO3)3•2H2O as catalyst
Wang, Min
Song, Zhi-Guo
Zhang, Ting-Ting
MONATSHEFTE FUR CHEMIE, 2010, 141 (09): : 993 - 996
[7] Multicomponent domino process for the synthesis of some novel 5-(arylidene)-3-((1-aryl-1H-1,2,3-triazol-4-yl)methyl)-thiazolidine-2,4-diones using PEG-400 as an efficient reaction medium and their antimicrobial evaluation
Sindhu, Jayant
Singh, Harjinder
Khurana, J. M.
Sharma, Chetan
Aneja, K. R.
CHINESE CHEMICAL LETTERS, 2015, 26 (01) : 50 - 54

← 1 →