Abstract
1,2,3-Triazoles were prepared in good to modest yields by cycloaddition of alkyl azides
onto enol ethers under solventless conditions. The reaction can access ring-fused
triazoles that are unavailable by azide-alkyne cycloadditions and is easily scalable.
The 1,2,3-triazole products bear functionality that may be readily derivatized.
Key words
azides - cycloadditions - heterocycles - nitrogen - regioselectivity
References
<A NAME="RM10204SS-1">1 </A>
Katritzky AR.
Rogovoy BV.
Chem. Eur. J.
2003,
9:
4586
<A NAME="RM10204SS-2">2 </A>
Yokoyama M.
Nakao E.
Sujuno K.
Watanabe S.
Togo H.
Heterocycles
1990,
31:
1669
<A NAME="RM10204SS-3">3 </A>
Caamano O.
Figueira MJ.
Fernandez R.
Garcia MD.
Nieto MI.
De Clerq E.
Balzarini J.
Nucleosides, Nucleotides Nucleic Acids
2001,
20:
1137
<A NAME="RM10204SS-4">4 </A>
Vicentini CB.
Brandolini V.
Guarneri M.
Farmaco
1992,
47:
1021
<A NAME="RM10204SS-5">5 </A>
Chan TR.
Hilgraf R.
Sharpless KB.
Fokin VV.
Org. Lett.
2004,
6:
2853
<A NAME="RM10204SS-6">6 </A>
Huisgen R.
Knorr R.
Möbius L.
Szeimies G.
Chem. Ber.
1965,
98:
4014
<A NAME="RM10204SS-7">7 </A>
Rostovstev VV.
Green LG.
Fokin VV.
Sharpless KB.
Angew. Chem. Int. Ed.
2002,
67:
3057
<A NAME="RM10204SS-8">8 </A>
Appukkuttan P.
Dehaen W.
Fokin VV.
Van der Eycken E.
Org. Lett.
2004,
6:
4223
<A NAME="RM10204SS-9">9 </A>
Scarpati R.
Sica D.
Lionetti A.
Gazz. Chim. Ital.
1963,
93:
90
<A NAME="RM10204SS-10">10 </A>
Huisgen R.
Möbius L.
Szeimies G.
Chem. Ber.
1965,
98:
1138
<A NAME="RM10204SS-11">11 </A>
Chabala JC.
Christensen BG.
Ratcliffe RW.
Tetrahedron Lett.
1985,
26:
5407
<A NAME="RM10204SS-12">12 </A>
Häbich D.
Barth W.
Heterocycles
1989,
29:
2083
<A NAME="RM10204SS-13">13 </A>
Peng W.-m.
Zhu S.-Z.
J. Fluorine Chem.
2002,
116:
81
<A NAME="RM10204SS-14">14 </A>
Pocar D.
Stradi R.
Rossi LM.
J. Chem. Soc., Perkin Trans. 1
1972,
619
<A NAME="RM10204SS-15">15 </A>
Pocar D.
Stradi R.
Rossi LM.
J. Chem. Soc., Perkin Trans. 1
1972,
769
<A NAME="RM10204SS-16">16 </A>
Nomura Y.
Takeuchi Y.
Tomoda S.
Ito MM.
Bull. Chem. Soc. Jpn.
1981,
46:
1800
<A NAME="RM10204SS-17">17 </A>
Palacios F.
Ochoa de Retana AM.
Pagalday J.
Sanchez JM.
Heterocycles
1995,
40:
543
<A NAME="RM10204SS-18">18 </A>
Palacios F.
Ochoa de Retana AM.
Pagalday J.
Sanchez JM.
Org. Prep. Proced. Int.
1995,
27:
603
<A NAME="RM10204SS-19">19 </A>
Peng W.
Zhu S.
Synlett
2003,
187
<A NAME="RM10204SS-20">20 </A>
Peng W.
Zhu S.
Tetrahedron
2003,
59:
4395
<A NAME="RM10204SS-21">21 </A>
Kadaba PK.
J. Org. Chem.
1992,
57:
3075
<A NAME="RM10204SS-22">22 </A>
Sasaki T.
Eguchi S.
Yamaguchi M.
Esaki T.
J. Org. Chem.
1981,
46:
1800
<A NAME="RM10204SS-23">23 </A>
Freeze S.
Norris P.
Heterocycles
1999,
51:
1807
<A NAME="RM10204SS-24">24 </A>
Huisgen R.
Möbius L.
Mueller G.
Stangl H.
Szeimies G.
Vernon JM.
Chem. Ber.
1965,
98:
3992
<A NAME="RM10204SS-25">25 </A>
Ondrus TT.
Knaus EE.
Giam CS.
Can. J. Chem.
1979,
57:
2342
<A NAME="RM10204SS-26">26 </A>
Warren BK.
Knaus EE.
J. Med. Chem.
1981,
24:
462
<A NAME="RM10204SS-27">27 </A>
Alvarez SG.
Alvarez MT.
Synthesis
1997,
413
<A NAME="RM10204SS-28">28 </A>
Mordini A.
Russo F.
Valacchi M.
Zani L.
Degl’Innocenti A.
Reginato G.
Tetrahedron
2002,
58:
7153
<A NAME="RM10204SS-29">29 </A>
Guanti G.
Riva R.
Tetrahedron: Asymmetry
2001,
12:
1185
<A NAME="RM10204SS-30">30 </A>
Lee LV.
Mitchell ML.
Huang S.-J.
Fokin VV.
Sharpless KB.
Wong C.-H.
J. Am. Chem. Soc.
2003,
125:
9588
<A NAME="RM10204SS-31">31 </A>
Gibson FS.
Park MS.
Rapoport H.
J. Org. Chem.
1994,
59:
7503
<A NAME="RM10204SS-32">32 </A>
Garcia Martinez A.
Martinez Alvarez R.
Arranz Aguirre J.
Subramanian LR.
J. Chem. Soc., Perkin Trans. 1
1986,
1595
<A NAME="RM10204SS-33">33 </A>
Kraus GA.
Krolski ME.
Sy J.
Org. Synth.
1988,
57:
202
<A NAME="RM10204SS-34">34 </A> See footnote 77 in:
Kolb HC.
Finn MG.
Sharpless KB.
Angew. Chem. Int. Eng.
2001,
41:
2004
<A NAME="RM10204SS-35">35 </A>
Fleming I.
Frontier Orbitals and Organic Reactions
Wiley;
London:
1976.
p.148
<A NAME="RM10204SS-36">36 </A>
Kulp SS.
J. Chem. Educ.
1988,
65:
742
<A NAME="RM10204SS-37">37 </A>
Penning TD.
Talley JJ.
Bertenshaw SR.
Carter JS.
Collins PW.
Doctor S.
Graneto MJ.
Lee LF.
Malecha JW.
Miyashiro JM.
Rogers RS.
Rogier DJ.
Yu SS.
Anderson GD.
Burton EG.
Cogburn JN.
Gregory SA.
Koboldt CM.
Perkins WE.
Seibert K.
Veenhuizen AW.
Zhang YY.
Isakson PC.
J. Med. Chem.
1997,
40:
1347
<A NAME="RM10204SS-38">38 </A>
Demko ZP.
Sharpless KB.
J. Org. Chem.
2001,
66:
7945
<A NAME="RM10204SS-39">39 </A>
L’abbe G.
Van Essche G.
Bull. Soc. Chim. Belg.
1991,
100:
289
