Abstract
A simple, convenient and practical protocol to synthesise 5-substituted 1H-tetrazoles from alcohols or aldehydes is reported. Using ammonia and sodium azide as nitrogen sources and Cu(NO3)2 as catalyst, benzylic alcohols and benzaldehydes were directly converted into 5-substituted 1H-tetrazoles in a one-pot procedure.
Keywords
References
1.
Hiskey M.
,
Chavez D.E.
,
Naud D.L.
,
Son S.F.
,
Berghout H.L.
, and
Bome C.A.
, Proc. Int. Pyrotech. Semin. , 2000 , 27 , 3 .
2.
Tuites R.C.
,
Whiteley T.E.
, and
Minsk L.M.
, US Patent 1,245,614 (1971 ).
3.
Koldobskii G.I.
, and
Ostrovskii V.A.
, Russ. Chem. Rev. , 1994 , 63 , 797 .
4.
Moderhack D.
, J. Prakt. Chem. , 1998 , 340 , 687 .
5.
Novakova V.
,
Roh J.
,
Gela P.
,
Kunes J.
, and
Zimcik P.
, Chem. Commun. , 2012 , 48 , 4326 .
6.
Aureggi V.
, and
Sedelmeier G.
, Angew. Chem. Int. Ed. , 2007 , 46 , 8440 .
7.
Sisido K.
,
Nabika K.
,
Isida T.
, and
Kozima S.
, J. Organomet. Chem. , 1971 , 33 , 337 .
8.
Duncia J.V.
,
Pierce M.E.
, and
Santella J.B.
, J. Org. Chem. , 1991 , 56 , 2395 .
9.
Garipova G.
,
Gautier A.
, and
Piettre S.R.
, Tetrahedron , 2005 , 61 , 4755 .
10.
Ettenhuber E.
, and
Ruhlmann K.
, Chem. Ber. , 1968 , 101 , 743 .
11.
Jin T.
,
Kitahara F.
,
Kamijo S.
, and
Yamamoto Y.
, Tetrahedron Lett. , 2008 , 49 , 2824 .
12.
Bonnamour J.
, and
Bolm C.
, Chem. Eur. J. , 2009 , 15 , 4543 .
13.
Cantillo D.
,
Gutmann B.
, and
Kappe C.O.
, J. Am. Chem. Soc. , 2011 , 133 , 4465 .
14.
Demko Z.P.
, and
Sharpless K.B.
, J. Org. Chem. , 2001 , 66 , 7945 .
15.
Himo F.
,
Demko Z.P.
,
Noodleman L.
, and
Sharpless K.B.
, J. Am. Chem. Soc. , 2003 , 125 , 9983 .
16.
Patil U.B.
,
Kumthekar K.R.
, and
Nagarkar J.M.
, Tetrahedron Lett. , 2012 , 53 , 3706 .
17.
Akhlaghinia B.
, and
Rezazadeh S.
, J. Braz. Chem. Soc. , 2012 , 23 , 2197 .
18.
Khan K.M.
,
Fatima I.
,
Saad S.M.
,
Taha M.
, and
Voelter W.
, Tetrahedron Lett. , 2016 , 57 , 523 .
19.
Kantam M.L.
,
Shiva Kumar K.B.
, and
Sridhar C.
, Adv. Synth. Catal. , 2005 , 347 , 1212 .
20.
Lang L.
,
Li B.
,
Liu W.
,
Jiang L.
,
Xu Z.
, and
Yin G.
, Chem. Commun. , 2010 , 46 , 448 .
21.
Sreedhar B.
,
Kumar A.S.
, and
Yada D.
, Tetrahedron Lett. , 2011 , 52 , 3565 .
22.
Yapuri U.
,
Palle S.
,
Gudaparthi O.
,
Narahari S.R.
,
Rawat D.K.
,
Mukkanti K.
, and
Vantikommu J.
, Tetrahedron Lett. , 2013 , 54 , 4732 .
23.
Aridoss G.
, and
Laali K.K.
, Eur. J. Org. Chem. , 2011 , 6343 .
24.
Abdollahi-Alibeik M.
, and
Moaddeli A.
, New J. Chem. , 2015 , 39 , 2116 .
25.
Yin W.Y.
,
Wang C.M.
, and
Huang Y.
, Org. Lett. , 2013 , 15 , 1850 .
26.
Heravi M.M.
,
Fazeli A.
,
Oskooie H.A.
,
Beheshtiha Y.S.
, and
Valizadeh H.
, Synlett , 2012 , 23 , 2927 .
27.
Tao C.Z.
,
Liu W.W.
,
Lv A.F.
,
Sun M.M.
,
Tian Y.
,
Wang Q.
, and
Zhao J.
, Synlett , 2010 , 21 , 1355 .
28.
Tao C.Z.
,
Lv A.F.
,
Zhao N.
,
Yang S.
,
Liu X.L.
,
Zhou J.
,
Liu W.W.
, and
Zhao J.
, Synlett , 2011 , 22 , 134 .
29.
Xu H.J.
,
Zhao Y.Q.
,
Feng T.
, and
Feng Y.S.
, J. Org. Chem. , 2012 , 77 , 2878 .
30.
Yang C.T.
,
Zhang Z.Q.
,
Liu Y.C.
, and
Liu L.
, Angew. Chem. Int. Ed. , 2011 , 50 , 3904 .
31.
Yang C.T.
,
Zhang Z.Q.
,
Liang J.
,
Liu J.H.
,
Lu X.Y.
,
Chen H.H.
, and
Liu L.
, J. Am. Chem. Soc. , 2012 , 134 , 11124 .
32.
Wang G.
,
Jiang J.
,
Bu X.
,
Dai J.
,
Xu J.
,
Fu Y.
, and
Xu H.
, Org. Lett. , 2015 , 17 , 3682 .
33.
Ebrahim-Alkhalil A.
,
Zhang Z.
,
Gong T.
,
Su W.
,
Lu X.
,
Xiao B.
, and
Fu Y.
, Chem. Commun. , 2016 , 52 , 4891 .
34.
Allen S.E.
,
Walvoord R.R.
,
Padilla-Salinas R.
, and
Kozlowski M.C.
, Chem. Rev. , 2013 , 113 , 6234 .
35.
Tao C.Z.
,
Liu F.
,
Zhu Y.M.
,
Liu W.W.
, and
Cao Z.L.
, Org. Biomol. Chem. , 2013 , 11 , 3349 .
36.
Nammalwar B.
,
Muddala N. P.
,
Pitchimani R.
, and
Bunce R.A.
, Molecules , 2015 , 20 , 22757 .
37.
Sharghi H.
,
Ebrahimpourmoghaddam S.
, and
Doroodmand M.M.
, J. Organomet. Chem. , 2013 , 738 , 41 .
38.
Butler R.N.
, and
McEvoy T.M.
, J. Chem. Soc., Perkin Trans. 2 , 1978 , 1087 .
39.
Wang Z.
,
Liu Z.
, and
Cheon S.H.
, Bull. Korean Chem. Soc. , 2015 , 36 , 198 .
40.
Sridhar M.
,
Mallu K.K.R.
,
Jillella R.
,
Godala K.R.
,
Beeram C.R.
, and
Chinthala N.
, Synthesis , 2013 , 45 , 507 .
