Abstract
A series of styryl substituted semicarbazides were synthesised by reaction of trans-styryl isocyanate, prepared by Curtius rearrangement of cinnamoyl azide, with acid hydrazides under microwave irradiation using a one-pot procedure. The effects of microwave irradiation in promoting the condensation of trans-styryl isocyanate with hydrazides were investigated alongside a conventional heating method (oil bath at 120 °C). When compared with classical methods, microwave irradiation has the advantages of mild conditions, easy handling, and high yields. The products have been characterised by analytical and spectral (IR and 1H NMR) data.
References
1.
Bose A.K.
,
Manhas M.S.
,
Ganguly S.N.
,
Sharma A.H.
, and
Banik B.K.
, Synthesis , 2002 , 32 , 1579 .
2.
Wang X.C.
,
Wang M.G.
,
Quan Z.J.
, and
Li Z.
, Synth. Commun. , 2005 , 35 , 2881 .
3.
Li Z.
,
Yu J.L.
,
Ding R.B.
,
Wang Z.Y.
, and
Wang X.C.
, Synth. Commun. , 2005 , 35 , 2981 .
4.
Takumi M.
,
Takanobu K.
,
Takatoshi I.
, and
Toshiyuki M.
, Synth. Commun. , 2000 , 30 , 1675 .
5.
Vidalu J.L.
,
Calmel F.
, and
Bigg D.
, J. Med. Chem. , 1994 , 37 , 689 .
6.
Gil M.J.
,
Mañú M.A.
, and
Arteaga C.
, Bioorg. Med. Chem. Lett. , 1999 , 16 , 2321 .
7.
Chalina E.G.
,
Chakarova L.
, and
Staneva D.T.
, Eur. J. Med. Chem. , 1998 , 33 , 985 .
8.
Arrieta A.
, and
Palomo C.
, Tetrahedron Lett. , 1981 , 22 , 1729 .
9.
Batey R.A.
,
Santhakumar V.
,
Yoshina-Ishii C.
, and
Taylor S.D.
, Tetrahedron Lett. , 1998 , 39 , 6267 .
10.
Chai L.Q.
,
Zhang H.S.
,
Zhang Y.L.
, and
Cui K.
, J. Chem. Res. , 2012 , 36 , 12 .
11.
Wang X.C.
,
Chai L.Q.
,
Wang M.G.
,
Quan Z.J.
, and
Li Z.
, Synth. Commun. , 2006 , 36 , 645 .
12.
Chai L.Q.
,
Zhang H.S.
,
Dong W.K.
, and
Zhao Y.L.
, Phosphorus, Sulfur, Silicon , 2010 , 185 , 1332 .
13.
Chai L.Q.
,
Chen Y.X.
,
Chen W.P.
, and
Ding Q.
, Phosphorus, Sulfur, Silicon , 2009 , 184 , 453 .
14.
Chai L.Q.
,
Chen W.P.
,
Wang X.Q.
, and
Ge J.L.
, Phosphorus, Sulfur, Silicon , 2007 , 182 , 2491 .
15.
Tanaka S.
, J. Am. Chem. Soc. , 1951 , 73 , 872 .
16.
Fan N.T.
, Dictionary of organic synthesis , Beijing University of Technology Publishing House , Beijing , 1992 , pp. 214 .
17.
Husain M.I.
, and
Amir M.
, J. Ind. Chem. Soc. , 1986 , 63 , 317 .
18.
Forster M.O.
, J. Chem. Soc. , 1909 , 95 , 437 .
19.
Jones L.W.
, and
Mason J.P.
, J. Am. Chem. Soc. , 1927 , 49 , 2531 .
20.
Li Z.G.
, Preparation of organic intermediates , Chemical Industry Publishing House , Beijing , 2001 , pp. 76 –77 .