Reduction of alkyl and aryl azides with sodium thiophosphate in aqueous solutions

被引：16

作者：

Norcliffe, Jennifer L. ^{[1
]}

Conway, Louis P. ^{[1
]}

Hodgson, David R. W. ^{[1
]}

机构：

[1] Univ Durham, Dept Chem, Sci Labs, Durham DH1 3LE, England

来源：

TETRAHEDRON LETTERS | 2011年 / 52卷 / 21期

基金：

英国工程与自然科学研究理事会;

关键词：

Aqueous; Azide; Reduction; Thiophosphate; THIO ACID/AZIDE AMIDATION; 5'-AMINO-5'-DEOXYGUANOSINE-5'-N-PHOSPHORAMIDATE; MECHANISM;

D O I：

10.1016/j.tetlet.2011.03.083

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple aqueous method for the conversion of alkyl and aryl azides into the corresponding amines using trisodium thiophosphate is presented. Thiophosphate is converted into phosphate during these formal reduction processes. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：2730 / 2732

页数：3

共 15 条

[1] Library of 1,4-Disubstituted 1,2,3-Triazole Analogs of Oxazolidinone RNA-Binding Agents [J].

Acquaah-Harrison, George ;

Zhou, Shu ;

Hines, Jennifer V. ;

Bergmeier, Stephen C. .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2010, 12 (04) :491-496

[2]

Alvarez SG, 1997, SYNTHESIS-STUTTGART, P413

[3] Thio acid/azide amidation:: An improved route to N-acyl sulfonamides [J].

Barlett, KN ;

Kolakowski, RV ;

Katukojvala, S ;

Williams, LJ .

ORGANIC LETTERS, 2006, 8 (05) :823-826

[4] STRUCTURE-REACTIVITY CORRELATION FOR HYDROLYSIS OF PHOSPHORAMIDATE MONOANIONS [J].

BENKOVIC, SJ ;

SAMPSON, EJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (16) :4009-&

[5] Aqueous methods for the preparation of 5′-substituted guanosine derivatives [J].

Brear, Paul ;

Freeman, Gemma R. ;

Shankey, Mark C. ;

Trmcic, Milena ;

Hodgson, David R. W. .

CHEMICAL COMMUNICATIONS, 2009, (33) :4980-4981

[6]

Fringuelli F, 2000, SYNTHESIS-STUTTGART, P646

[7] Revisiting nucleophilic substitution reactions: Microwave-assisted synthesis of azides, thiocyanates, and sulfones in an aqueous medium [J].

Ju, Yuhong ;

Kumar, Dalip ;

Varma, Rajender S. .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (17) :6697-6700

[8] Mechanism of thio acid/azide amidation [J].

Kolakowski, RV ;

Shangguan, N ;

Sauers, RR ;

Williams, LJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (17) :5695-5702

[9] Thioamides via thiatriazolines [J].

Kolakowski, RV ;

Ning, SG ;

Williams, LJ .

TETRAHEDRON LETTERS, 2006, 47 (07) :1163-1166

[10]

Lee JG, 2001, SYNTHESIS-STUTTGART, P81

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