An efficient, inexpensive, and shelf-stable diazotransfer reagent: Imidazole-1-sulfonyl azide hydrochloride

被引：515

作者：

Goddard-Borger, Ethan D. ^{[1
]}

Stick, Robert V. ^{[1
]}

机构：

[1] Univ Western Australia, Sch Biomed Biomol & Chem Sci, Crawley, WA 6009, Australia

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 19期

关键词：

D O I：

10.1021/ol701581g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The design and synthesis of a new diazotransfer reagent, imidazole-l-sulfonyl azide hydrochloride, are reported. This reagent has proven to equal triflyl azide in its ability to act as a "diazo donor" in the conversion of both primary amines into azides and activated methylene substrates into diazo compounds. Crucially, this reagent can be prepared in a one-pot reaction on a large scale from inexpensive materials, is shelf-stable, and is conveniently crystalline.

引用

页码：3797 / 3800

页数：4

共 21 条

[1] Metal catalyzed diazo transfer for the synthesis of azides from amines [J].

Alper, PB ;

Hung, SC ;

Wong, CH .

TETRAHEDRON LETTERS, 1996, 37 (34) :6029-6032

[2] AMINO-SUGARS .35. SYNTHETIC STUDIES ON GLYCOCINNAMOYLSPERMIDINES - SYNTHESIS OF A KEY INTERMEDIATE OF THE DIAMINOHEXOSE MOIETY - ETHYL PARA-[4-AMINO-2-(TERT-BUTOXYCARBONYL)AMINO-2,4,6-TRIDEOXY-ALPHA-D-GLUCOPYRANOSYLOXY]CINNAMATE [J].

ARAKI, K ;

HASHIMOTO, H ;

YOSHIMURA, J .

CARBOHYDRATE RESEARCH, 1982, 109 (NOV) :143-160

[3] A practical procedure for the preparation of carbamates from azides [J].

Ariza, X ;

Urpí, F ;

Vilarrasa, J .

TETRAHEDRON LETTERS, 1999, 40 (42) :7515-7517

[4] CuI-catalyzed alkyne-azide "click" cycloadditions from a mechanistic and synthetic perspective [J].

Bock, VD ;

Hiemstra, H ;

van Maarseveen, JH .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (01) :51-68

[5] On the reaction of acyl chlorides and carboxylic anhydrides with phosphazenes [J].

Bosch, I ;

Gonzalez, A ;

Urpi, F ;

Vilarrasa, J .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (16) :5638-5643

[6] TRIFLUOROMETHANESULFONYL AZIDE - ITS REACTION WITH ALKYL AMINES TO FORM ALKYL AZIDES [J].

CAVENDER, CJ ;

SHINER, VJ .

JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (22) :3567-&

[7]

Doyle M. P., 1998, Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides

[8] RECENT ADVANCES IN THE STAUDINGER REACTION [J].

GOLOLOBOV, YG ;

KASUKHIN, LF .

TETRAHEDRON, 1992, 48 (08) :1353-1406

[9] ARYLSULPHAMOYL AZIDES - IMPROVED SYNTHESIS OF CHLOROSULPHONYL AZIDE AND ITS REACTION WITH ARYLAMINES [J].

GRIFFITH, J .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (19) :3191-+

[10] DESIGN AND REACTIVITY OF ORGANIC FUNCTIONAL-GROUPS - IMIDAZOLYLSULFONATE (IMIDAZYLATE) - AN EFFICIENT AND VERSATILE LEAVING GROUP [J].

HANESSIAN, S ;

VATELE, JM .

TETRAHEDRON LETTERS, 1981, 22 (37) :3579-3582

← 1 2 3 →