Abstract
N-acetylureas were synthesised regioselectively from 1,3-disubstituted selenoureas and zinc acetate. Regioselectivity was dependent on the pKa of the amine attached to the selenourea and occurred towards the amine with the lower pKa. The approach provided a simple, mild and efficient way to construct various N-acetylureas regioselectively in moderate to good yields (53–88%). A plausible mechanism was proposed for the formation of N-acetylureas.
References
1.
Katritzky A.R.
,
Kirichenko N.
,
Rogovoy B.V.
,
Kister J.
, and
Tao H.
, Synthesis , 2004 , 11 , 1799 .
2.
Singh C.B.
,
Murru S.
,
Kavala V.
, and
Patel B.K.
, Org. Lett. , 2006 , 8 , 5397 .
3.
Singh C.B.
,
Murru S.
,
Kavala V.
, and
Patel B.K.
, J. Chem. Res. , 2007 , 136 .
4.
Murru S.
,
Singh C.B.
,
Kavala V.
, and
Patel B.K.
, Tetrahedron , 2008 , 64 , 1931 .
5.
Sommen G.L.
,
Linden A.
, and
Heimgartner H.
, Tetrahedron , 2006 , 62 , 3344 .
6.
Toyoda Y.
,
Garud D.R.
, and
Koketsu M.
, Heterocycles , 2009 , 78 , 449 .
7.
Koketsu M.
,
Suzuki N.
, and
Ishihara H.
, J. Org. Chem. , 1999 , 64 , 6473 .
8.
Welling K.
,
Mulder R.
, and
van Daalen J. J.
, Agric. Food Chem. , 1973 , 21 , 348 .
9.
Nakagawa Y.
,
Kitahara K.
,
Nishioka T.
,
Iwamura H.
, and
Fujita T.
, Pestic. Biochem. Physiol. , 1984 , 21 , 309 .
10.
Goodman L.S.
, and
Gilman A.
, The pharmacological basis of therapeutics. MacMillan , New York , 1980 , 6th edn.
11.
Kricheldorf H.R.
, and
Stober O.
, Eur. Polym. J. , 1992 , 28 , 1377 .
12.
Kishikawa K.
,
Yamamoto M.
,
Kohmoto S.
, and
Yamada K.
, J. Org. Chem. , 1989 , 54 , 2428 .
13.
Abdel-Aziz A.A.M.
,
Matsunaga H.
, and
Kunieda T.
, Tetrahedron Lett. , 2001 , 42 , 6565 .
14.
Brambilla E.
,
Di Salle E.
,
Briatico G.
,
Mantegani S.
, and
Temperilli A.
, Eur. J. Med. Chem. , 1989 , 24 , 421 .
15.
Akcamur Y.
,
Sener A.
,
Ipekoglu A.M.
, and
Kollenz G.
, J. Heterocycl. Chem. , 1997 , 34 , 221 .
16.
Mu X.J.
,
Zou J.P.
,
Qian Q.F.
, and
Zhang W.
, Tetrahedron Lett. , 2006 , 47 , 2323 .
17.
Singh C.B.
,
Ghosh H.
,
Murru S.
, and
Patel B.K.
, J. Org. Chem. , 2008 , 73 , 2924 .
18.
Ghosh H.
,
Sarkar S.
, and
Patel B.K.
, J. Sulfur Chem. , 2010 , 31 , 1 .
