3-Pyridinesulfonyl azide: A useful reagent for radical azidation

被引：28

作者：

Panchaud, P ^{[1
]}

Renaud, P ^{[1
]}

机构：

[1] Univ Bern, Dept Chem & Biochem, CH-3012 Bern, Switzerland

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2004年 / 346卷 / 08期

关键词：

amination; azides; carboazidation; C-C bond formation; radicals; synthetic methods;

D O I：

10.1002/adsc.200404038

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Radical azidations and carboazidations have been achieved using 3-pyridinesulfonyl azide as azidating agent. Due to its base properties and its polarity, the excess of reagent is readily removed at the end of the reaction by filtration through silica gel or by extraction with either aqueous I M HCl or 1 M CuSO4. The use of this reagent greatly facilitates the tedious purifications of the final azides frequently encountered when reactions are run according to the original procedure involving benzenesulfonyl azide.

引用

页码：925 / 928

页数：4

共 11 条

[1] SYNTHESIS AND ANTINOCICEPTIVE ACTIVITY OF 1-METHYLPIPERIDYLIDENE-2-(PYRIDYL)SULFONAMIDES AND RELATED DIHYDROPYRIDYL ANALOGS [J].

BUOLAMWINI, JK ;

KNAUS, EE .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1993, 28 (06) :447-453

[2] SOME REACTIONS OF PYRIDINE-3-SULFONYL CHLORIDE [J].

CREMLYN, RJ ;

JONES, GP ;

SWINBOURNE, FJ ;

YUNG, K .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1980, 8 (02) :189-196

[3] SYMMETRICAL AND UNSYMMETRICAL QUADRUPLY AZA BRIDGED CLOSELY INTERSPACED COFACIAL BIS(5,10,15,20-TETRAPHENYLPORPHYRIN)S .2. SYNTHESIS, CHARACTERIZATION, AND CONFORMATIONAL EFFECTS OF SOLVENTS [J].

KARAMAN, R ;

BLASKO, A ;

ALMARSSON, O ;

ARASASINGHAM, R ;

BRUICE, TC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (12) :4889-4898

[4] A novel approach for the formation of carbon - Nitrogen bonds: Azidation of alkyl radicals with sulfonyl azides [J].

Ollivier, C ;

Renaud, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (20) :4717-4727

[5] Radical carboazidation: Expedient assembly of the core structure of various alkaloid families [J].

Panchaud, P ;

Ollivier, C ;

Renaud, P ;

Zigmantas, S .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (08) :2755-2759

[6] A convenient tin-free procedure for radical carboazidation and azidation [J].

Panchaud, P ;

Renaud, P .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (09) :3205-3207

[7]

PANCHAUD P, 2004, IN PRESS CHEM EUR J, V10

[8]

Renaud P, 2002, ANGEW CHEM INT EDIT, V41, P3460, DOI 10.1002/1521-3773(20020916)41:18<3460::AID-ANIE3460>3.0.CO

[9]

2-6

[10] SOME REACTIONS OF 1-ALKYL-1,2,3,4-TETRAHYDROPYRIDINES WITH ORGANIC AZIDES - SYNTHESIS OF 1-ALKYLPIPERIDYLIDENE-2-SULFONAMIDES [J].

WARREN, BK ;

KNAUS, EE .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1988, 25 (05) :1379-1381

← 1 2 →