Abstract
Reaction between azides and acetylenes catalysed by ZnO nanoparticles (ZnO NPs) in solvent EtOH at room temperature provide a simple and efficient one-pot route for the synthesis of 1,4-disubstituted 1,2,3-triazoles in excellent yields. 1,2,3-Triazoles are used in various agricultural, industrial and medical fields.
References
1.
Kolb H.C.
,
Sharpless K.B.
, Drug Discov. Today , 2003 , 8 , 1128 .
2.
Yanase Y.
,
Yoshikawa Y.
,
Kawashima H.
,
Takashi A.
,
Akase T.
, Jpn. Kokai Tokkyo Koho JP 2001072507 ; Chem. Abstr. , 2001, 134 , 233062.
3.
Abdennabi A.M.S.
,
Abdulhadi A.I.
,
Abu-Orabi S.T.
,
Saricimen H.
, Corros. Sci. , 1996 , 38 , 1791 .
4.
Rody J.
,
Slongo M.
, Eur. Pat. 80 810 394 , 1981; Chem. Abstr. , 1981 , 95 , 187267 .
5.
Guenther D.
,
Nestler H.J.
,
Roesher G.
,
Schinzel E.
, Ger. Pat. 615164 , 1980; Chem. Abstr. , 1980 , 93 , 73786 .
6.
Alvarez R.
,
Velazquez S.
,
San F.
,
Aquaro S.
,
De C.
,
Perno C.
,
Karlsson A.
,
Balzarin J.
,
Camarasa M.J.
, J. Med. Chem. , 1994 , 37 , 4185 .
7.
Sanghvi Y.S.
,
Bhattacharya B.K.
,
Kini G.D.
,
Matsumoto S.S.
,
Larson S.B.
,
Jolley W.B.
,
Robins R.K.
,
Revankar G.R.
, J. Med. Chem. , 1990 , 33 , 336 .
8.
Makabe O.
,
Suzuki H.
,
Umezawa S.
, Bull. Chem. Soc. Jpn , 1977 , 50 , 2689 .
9.
Hupe D.J.
,
Boltz R.
,
Cohen C.J.
,
Felix J.
,
Ham E.
,
Miller D.
,
Soderman D.
,
Skiver D.V.
, J. Biolog. Chem. , 1991 , 266 , 10136 .
10.
Bascal Z.
,
Holden-dye L.
,
Willis R.J.
,
Dmith S.W.G.
,
Walker R.J.
, Parasitology , 1996 , 112 , 253 .
11.
Biagi G.
,
Giorgi I.
,
Livi O.
,
Lucacchini A.
,
Martini C.
,
Scartoni V.
, J. Pharm. Sci. , 1993 , 82 , 893 .
12.
Peto C.
,
Batta G.
,
Gyorgydeak Z.
,
Sztaricskai F.
, J. Carbohydrate Chem. , 1996 , 15 , 465 .
13.
Kume M.
,
Kubota T.
,
Kimura Y.
,
Nakashimisu H.
,
Motokawa K.
,
Nakano M.
, J. Antibiotics , 1993 , 46 , 177 .
14.
Mearman R.C.
,
Newall C.E.
,
Tonge A.P.
, J. Antibiotics , 1984 , 37 , 885 .
15.
Buckle D.R.
,
Rockell C.J.M.
,
Smith H.
,
Spicer B.A.
, J. Med. Chem. , 1986 , 29 , 2262 .
16.
Finley K.T.
, The chemistry of heterocyclic compounds , Vol 39 .
Montgomery J.A.
ed.; New York , John Wiley & Sons , 1980 .
17.
Huisgen R.
, 1,3-Dipolar cycloaddition chemistry.
Padwa A.
ed., New York , John Wiley , 1984 , pp. 1 –176 .
18.
Rostovtsev V.V.
,
Green L.G.
,
Fokin V.V.
,
Sharpless K.B.
, Angew. Chem. Int. Ed. , 2002 , 41 , 2596 .
19.
Lee L.V.
,
Mitchell L.
,
Huang S.J.
,
Fokin V.V.
,
Sharpless K.B.
,
Wong C.H.
, J. Am. Chem. Soc. , 2003 , 125 , 9588 .
20.
Feldman A.K.
,
Colasson B.
,
Fokin V.V.
, Org. Lett. , 2004 , 6 , 3897 .
21.
Appukkuttan P.
,
Dehaen W.
,
Fokin V.V.
,
Eycken E.V.
, Org. Lett. , 2004 , 6 , 4223 .
22.
Wang Q.
,
Chan T.R.
,
Hilgraf R.
,
Fokin V.V.
,
Sharpless K.B.
,
Finn M.G.
, J. Am. Chem. Soc. , 2003 , 125 , 3192 .
23.
Pachón L.D.
,
Maarseveen J.H.
,
Rothenberg G.
, Adv. Synth. Catal. , 2005 , 347 , 811 .
24.
Reddy K.R.
,
Rajgopal K.
,
Kantam M.L.
, Synlett , 2006 , 957 .
25.
Zhang L.
,
Chen X.
,
Xue P.
,
Sun H.H.Y.
,
Williams I.D.
,
Sharpless K.B.
,
Fokin V.V.
,
Jia G.
, J. Am. Chem. Soc. , 2005 , 127 , 15998 .
26.
Leadbeater N.E.
,
Marco M.
,
Tominack B.
J. Org. Lett. , 2003 , 5 , 3919 .
27.
Scriven E.F.V.
,
Turnbull K.
, Chem. Rev. , 1988 , 88 , 297 .
28.
Maksikova A.V.
,
Serebryakova E.S.
,
Tikhonova L.G.
,
Vereshagin L.I.
, Chem. Heterocycl. Compd , 1980 , 1284 .
29.
Kacprzak K.
, Synlett , 2005 , 943 .
30.
Sadeghi B.
,
Mirjalili B.F.
,
Hashemi M.M.
, Tetrahedron Lett. , 2008 , 48 , 8554 .
31.
Mirjalili B.F.
,
Hashemi M.M.
,
Sadeghi B.
,
Emtiazi H.
, J. Chin. Chem. Soc. , 2009 , 56 , 386 .
32.
Tang E.
,
Tian B.
,
Zheng E.
,
Fu C.
,
Cheng G.
, Chem. Eng. Comm. , 2008 , 195 , 479 .
33.
L'abbé G.
,
Bruynseels M.
,
Delbeke P.
, and
Toppet S.
, J. Heterocycl. Chem. , 1990 , 27 , 2021 .
34.
Odlo K.
,
Andre Hydahl E.
,
Vidar Hansen T.
, Tetrahedron Lett. , 2007 , 48 , 2097 .
35.
Anderson W.K.
,
Jones A.N.
, J. Med. Chem. , 1984 , 27 , 1559 .
36.
Oliva C.G.
,
Jagerovic N.
,
Goya P.
,
Alkorta I.
,
Elguero J.
,
Cuberes R.
,
Dordal A.
, Arkivok , 2010 , (ii ), 127 .
37.
Sarmiento-Sánchez J.I.
,
Ochoa-Terán A.
,
Rivero I.A.
, Arkivok , 2010 , (ix ), 177 .
