[3+2] cycloaddition reactions in the solid-phase synthesis of 1,2,3-triazoles

被引：44

作者：

Gao, Yongnian ^{[1
]}

Lam, Yulin ^{[1
]}

机构：

[1] Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 15期

关键词：

D O I：

10.1021/ol0611494

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and regioselective procedure for the synthesis of 1,2,3-triazoles via a [3+2] cycloaddition of polymer-bound vinyl sulfone and sodium azide is described. Microwave irradiation provided significant rate enhancement in all steps of the three-step protocol. A representative set of 23 compounds was prepared.

引用

页码：3283 / 3285

页数：3

共 20 条

[1] Synthesis of 4-aryl-1H-1,2,3-triazoles through TBAF-catalyzed [3+2] cycloaddition of 2-aryl-1-nitroethenes with TMSN3 under solvent-free conditions [J].

Amantini, D ;

Fringuelli, F ;

Piermatti, O ;

Pizzo, F ;

Zunino, E ;

Vaccaro, L .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (16) :6526-6529

[2] MICROWAVE-ASSISTED ORGANIC-REACTIONS [J].

CADDICK, S .

TETRAHEDRON, 1995, 51 (38) :10403-10432

[3]

CHAKRASALI RT, 1988, SYNTHESIS-STUTTGART, P851

[4] Trimethylsilyl-directed 1,3-dipolar cycloaddition reactions in the solid-phase synthesis of 1,2,3-triazoles [J].

Coats, SJ ;

Link, JS ;

Gauthier, D ;

Hlasta, DJ .

ORGANIC LETTERS, 2005, 7 (08) :1469-1472

[5]

Dolly, 2004, HETEROCYCLES, V63, P1175

[6]

DONDG Z, 1993, AUST J CHEM, V46, P1431

[7] γ-Methyl-substituted-γ-butyrolactones:: solid-phase synthesis employing a cyclisation-cleavage strategy [J].

Gouault, N ;

Cupif, JF ;

Sauleau, A ;

David, M .

TETRAHEDRON LETTERS, 2000, 41 (38) :7293-7297

[8] Solid-phase synthesis of 1,2,3-triazoles via 1,3-dipolar cycloaddition [J].

Harju, K ;

Vahermo, M ;

Mutikainen, I ;

Yli-Kauhaluoma, J .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2003, 5 (06) :826-833

[9] STERIC EFFECTS ON THE REGIOSELECTIVITY OF AN AZIDE-ALKYNE DIPOLAR CYCLOADDITION REACTION - THE SYNTHESIS OF HUMAN-LEUKOCYTE ELASTASE INHIBITORS [J].

HLASTA, DJ ;

ACKERMAN, JH .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (21) :6184-6189

[10] Recognition-mediated regiocontrol of a dipolar cycloaddition reaction [J].

Howell, SJ ;

Spencer, N ;

Philp, D .

TETRAHEDRON, 2001, 57 (23) :4945-4954

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