Abstract
This brief review article describes the progress made in the
synthesis of 1,2,3-triazole-fused heterocycles, over the last ten years,
mainly by azide-alkyne cycloaddition reactions. In this
article, the emphasis is on the various aspects of 1,3-dipolar cycloaddition
reactions, especially intramolecular azide-alkyne dipolar cycloaddition
reactions.
1 Introduction
2 Synthesis of Fused Triazoles
2.1 Synthesis of 1,2,3-Triazole-Fused Heterocycles by Huisgen (Thermal)
1,3-Cycloaddition Reactions
2.2 Microwave-Assisted 1,3-Dipolar Cycloaddition Reactions for
the Synthesis of Condensed Triazoles
2.3 Copper-Catalyzed Cycloaddition Reactions for the Synthesis
of Condensed Triazoles
2.4 Copper/Other-Metal-Catalyzed Cycloaddition Reactions for
the Synthesis of Condensed Triazoles
2.5 Synthesis of Triazole-Containing Macrocycles by Azide-Alkyne
1,3-Dipolar Cycloaddition Reactions
3 Conclusion
Key words
1,2,3-triazole - azide - alkyne - cycloaddition - heterocycles
References 1 Present address: Department of Chemical
Sciences, Tezpur University, Napaam, Tezpur 784 028, Assam, India.
2a
Alvarez R.
Valaquez S.
San F.
Aquaro S.
De C.
Penro CF.
Karlsson A.
Balzarini J.
Camarasa MJ.
J. Med. Chem.
1994,
37:
4185
2b
Valquez S.
Alvarez R.
Perez C.
Cago F.
De C.
Balzarini J.
Camarasa MJ.
Antiviral
Chem. Chemother.
1998,
9:
481
3
Buckle DR.
Rockell CJM.
Smith H.
Spicer BA.
J.
Med. Chem.
1986,
29:
2262
4a
Vicentini CB.
Brandolini V.
Guarneri M.
Giori P.
Farmaco
1992,
47:
1021
4b
Fung-Tomc JC.
Huczko E.
Minassion B.
Bonner DP.
Antimicrob.
Agents Chemother.
1998,
42:
313
5
Palhagen S.
Canger R.
Henriksen O.
van Paryes JA.
Riviere ME.
Karolchyk MA.
Epilepsy
Res.
2001,
43:
115
6
Genin MJ.
Allwine DA.
Anderson DJ.
Barbachyn MR.
Emmert DE.
Garmon SA.
Graber DR.
Grege KC.
Hester JB.
Hutchinson DK.
Morris J.
Reischer RJ.
Ford CW.
Zurenko GE.
Hamel JC.
Schaadt RD.
Stapert D.
Yagi BH.
J.
Med. Chem.
2000,
43:
953
7
Bourne Y.
Kolb HC.
Radic Z.
Sharpless KB.
Taylor P.
Marchot P.
Proc. Natl. Acad. Sci. U.S.A.
2004,
101:
1449
8
Fan W.-Q.
Katritzky AR. In Comprehensive Heterocyclic Chemistry II
Vol.
4:
Katritzky AR.
Rees CW.
Seriven EFV.
Elsevier Science;
Oxford:
1996.
p.1-26
9a
Huisgen R.
Knorr R.
Moebius L.
Szeimies G.
Chem. Ber.
1965,
98:
4014
9b
Huisgen R.
In 1,3-Dipolar Cycloaddition Chemistry
Padwa A.
Wiley;
New York:
1984.
p.1-176
10a
Rostovtsev VV.
Green LG.
Fokin VV.
Sharpless KB.
Angew. Chem. Int. Ed.
2002,
41:
2596
10b
Tornøe CW.
Meldal M.
Peptidotriazoles: Copper(I)-Catalyzed 1,3-Dipolar
Cycloadditions on Solid-Phase , In The Wave of the Future
Lebl M.
Houghten RA.
American
Peptide Society;
San Diego:
2001.
p.263
10c
Tornøe CW.
Christensen C.
Meldal M.
J. Org. Chem.
2002,
67:
3057
11a
Boren BC.
Narayan S.
Rasmussen LK.
Zhang L.
Zhao H.
Lin Z.
Jia G.
Fokin VV.
J.
Am. Chem. Soc.
2008,
130:
8923
11b
Zhang L.
Chen X.
Xue P.
Sun HHY.
Williams ID.
Sharpless KB.
Fokin VV.
Jia G.
J. Am. Chem.
Soc.
2005,
127:
15998
12
Declerck V.
Toupet L.
Martinez J.
Lamity F.
J. Org. Chem.
2009,
74:
2004
13
Sudhir VS.
Nasir Baig RB.
Chandrasekaran S.
Eur. J. Org. Chem.
2008,
2423
14
Sudhir VS.
Phani Kumar NY.
Nasir Baig RB.
Chandrasekaran S.
J.
Org. Chem.
2009,
74:
7588
15
Brawn PA.
Welzel M.
Lowe JT.
Panek JS.
Org. Lett.
2010,
12:
336
16
Mohapatra DK.
Maity PK.
Gonnade RG.
Chorghade MS.
Gurjar MK.
Synlett
2007,
1893
17
Couty F.
Durrat F.
Prim D.
Tetrahedron
Lett.
2004,
45:
3725
18
Oliva AI.
Christmann U.
Font D.
Cuevas F.
Ballester P.
Buschmann H.
Torrens A.
Yenes S.
Paricãs MA.
Org. Lett.
2008,
10:
1617
19
Li R.
Jansen DJ.
Datta A.
Org.
Biomol. Chem.
2009,
7:
1921
20a
Weijers CAGM.
Könst PM.
Franssen MCR.
Sudhölter EJR.
Org.
Biomol. Chem.
2007,
5:
3106
20b
Fringuelli F.
Piermatti O.
Pizzo F.
Vaccaro L.
J. Org. Chem.
1999,
64:
6094
21
Ko SH.
Lee K.-J.
J. Heterocycl. Chem.
2004,
41:
613
22
Majumdar KC.
Ray K.
Ganai S.
Ghosh T.
Synthesis
2010,
858
23
Majumdar KC.
Ray K.
Ganai S.
Synthesis
2010,
2101
24
Chambers CS.
Patel N.
Hemming K.
Tetrahedron
Lett.
2010,
51:
4859
25
Donald JR.
Martin SF.
Org. Lett.
2011,
13:
852
26
Gracias V.
Darczak D.
Gasiecki AF.
Djuric SW.
Tetrahedron Lett.
2005,
46:
9053
27
Park SP.
Ahn S.-H.
Lee K.-J.
Tetrahedron
2010,
66:
3490
28
Kim MS.
Yoon HJ.
Lee BK.
Kwon JH.
Lee WK.
Kim Y.
Ha H.-J.
Synlett
2005,
2187
29
Akritopoulou-Zanze I.
Gracious V.
Djuric SW.
Tetrahedron
Lett.
2004,
45:
8439
30
Röper S.
Franz MH.
Wartchow R.
Hoffmann HMR.
Org. Lett.
2003,
5:
2773
31
Hotha S.
Anegundi RI.
Natu AA.
Tetrahedron Lett.
2005,
46:
4585
32a
Beryozkina T.
Appukkuttan P.
Mont N.
Van der Eyken E.
Org. Lett.
2006,
8:
487
32b
Mont N.
Mehta VP.
Appukkuttan P.
Beryozkina T.
Toppet S.
Hecke KV.
Meervelt LV.
Voet A.
deMaeyer M.
Van der Eycken K.
J.
Org. Chem.
2008,
73:
7509
33
Chandrasekhar S.
Seenaiah M.
Kumar A.
Reddy CR.
Mamidyala SK.
Kumar CG.
Balasubramanian S.
Tetrahedron Lett.
2011,
52:
806
34
Hu Y.-Y.
Hu J.
Wang X.-C.
Guo LN.
Shu X.-Z.
Niu Y.-N.
Liang YM.
Tetrahedron
2010,
66:
80
35
Chowdhury C.
Mandal SB.
Achari B.
Tetrahedron
Lett.
2005,
46:
8531
36
Chowdhury C.
Mukherjee S.
Das B.
Achari B.
J. Org. Chem.
2009,
74:
3612
37
Chowdhury C.
Sasmal AK.
Dutta PK.
Tetrahedron Lett.
2009,
50:
2678
38
Yanai H.
Taguchi T.
Tetrahedron Lett.
2005,
46:
8639
39
van Maarseveen JH.
Horne WS.
Ghadiri MR.
Org. Lett.
2005,
7:
4503
40
Chandrasekhar S.
Rao CL.
Nagesh C.
Reddy CR.
Sridhar B.
Tetrahedron
Lett.
2007,
48:
5869
41
Ray A.
Manoj K.
Bhadbhade MM.
Mukhopadhyay R.
Bhattacharjya A.
Tetrahedron
Lett.
2006,
47:
2775
42
Pirali T.
Tron GC.
Zhu J.
Org.
Lett.
2006,
8:
4145
43
Crews P.
Manes LV.
Boehler M.
Tetrahedron
Lett.
1986,
27:
2797
44
Zabriskie TM.
Klocke JA.
Ireland CM.
Marcus AH.
Molinski TF.
Faulkner DJ.
Xu C.
Clardy J.
J.
Am. Chem. Soc.
1986,
108:
3123
45
Hu T.-S.
Tannert R.
Arndt H.-D.
Waldmann H.
Chem. Commun.
2007,
3942
46
Kelly AR.
Wei J.
Kesavan S.
Marié J.-C.
Windmon N.
Young DW.
Marcaurelle LA.
Org.
Lett.
2009,
11:
2257
47
Shafran EA.
Bakulev VA.
Rozin YA.
Shafran YM.
Chem.
Heterocycl. Compd. (Engl. Transl.)
2008,
44:
1040