Abstract
A series of asymmetric semicarbazides were synthesised using 3-coumarin isocyanate, which was prepared from 3-coumarinyl azide by Curtius rearrangement, with acid hydrazides under microwave irradiation using a one-pot procedure. This method has the advantages of mild conditions, easy handling and high yields. The products, which have been characterised by analytical and spectral data, have many medicinal and agrochemical applications.
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.
Wu J.
, and
Yang Z.
, J. Org. Chem. , 2001 , 66 , 7875 .
9.
Wu J.
,
Liao Y.
, and
Yang Z.
, J. Org. Chem. , 2001 , 66 , 3642 .
10.
Chenera B.
,
West M.L.
,
Finkel-stein J.A.
, and
Dreyer G.B.
, J. Org. Chem. , 1993 , 58 , 5605 .
11.
Arrieta A.
, and
Palomo C.
, Tetrahedron Lett. , 1981 , 22 , 1729 .
12.
Batey R.A.
,
Santhakumar V.
,
Yoshina-Ishii C.
, and
Taylor S.D.
, Tetrahedron Lett. , 1998 , 39 , 6267 .
13.
Wang X.C.
,
Chai L.Q.
,
Wang M.G.
,
Quan Z.J.
, and
Li Z.
, Synth. Commun. , 2006 , 36 , 645 .
14.
Chai L.Q.
,
Chen W.P.
,
Wang X.Q.
, and
Ge J.L.
, Phosphorus, Sulfur , 2007 , 182 , 2491 .
15.
Fan N. T.
, Dictionary of organic synthesis , Beijing University of Technology Publishing House , Beijing , 1992 , pp. 214 .
16.
Husain M.I.
, and
Amir M.
, J. Indian Chem. Soc. , 1986 , 63 , 317 .
