Abstract
A short and facile synthesis of a series of 1,2-dihydroquiazolin-4(3H)-ones was accomplished in good yields via the novel reductive cyclisation of o-nitrobenzamides with aldehydes or ketones promoted by the TiCl4/Sm system. Structures were established on the basis of elemental analysis, IR, 1H NMR and confirmed by a single-crystal X-ray diffraction analysis. The advantages of our method are easily accessible starting materials, convenient manipulation and moderate to high yields.
References
1.
(a)
McMurry J.E.
, Acc. Chem. Res. 1974 , 7 , 281 .
2.
McMurry J.E.
, Acc. Chem. Res. 1983 , 16 , 405 .
3.
McMurry J.E.
, Chem. Rev. 1989 , 89 , 1513 .
4.
Lenoir D.
, Synthesis 1989 , 883 .
5.
Fiirstner A.
, and
Bogdanovi B.
, Angew. Chem., Int. Ed. 1996 , 35 , 2443 .
6.
Shi D.Q.
,
Chen J. X.
,
Chai W. Y.
,
Chen W. X.
, and
Kao T. Y.
, Tetrahedron Lett. 1993 , 34 , 2963 .
7.
Zhou L.H.
,
Shi D. Q.
,
Gao Y.
,
Shen W. B.
,
Dai G. Y.
, and
Chen W. X.
, Tetrahedron Lett. 1997 , 38 , 2729 .
8.
Zhou L.H.
,
Tu S. J.
,
Shi D. Q.
,
Dai G. Y.
, and
Chen W. X.
, Synthesis , 1998 , 851 .
9.
(a)
Gravier D.
,
Dupin J. P.
,
Casadebaig F.
,
Hou G.
,
Boisseau M.
, and
Bernard H.
, Pharmazie , 1992 , 47 , 91 .
10.
Baker B.R.
,
Schaub R. E.
,
Joseph J. P.
,
McEvoy F. J.
, and
Williams J. H.
, J. Org. Chem. 1953 , 18 , 133 .
11.
Wolfe J.F.
,
Rathman T. L.
,
Sleevi M. C.
,
Campbell J. A.
, and
Greenwood T. D.
, J. Med. Chem. 1990 , 33 , 161 .
12.
(a)
Bogert M.T.
, and
Hand W. F.
, J. Am. Chem. Soc. 1902 , 24 , 1032 .
13.
Bogentoft C.
,
Kronberg L.
, and
Danielsson B.
, Acta. Pharm. Suec. 1969 , 6 , 485 .
14.
Stephen H.
, and
Wadge G.
, J. Chem. Soc. 1956 , 4420 .
15.
(a)
Takeuchi H.
,
Haguvara S.
, and
Eguchi S.
, Tetrahedron , 1989 , 45 , 6375 .
16.
Takeuchi H.
,
Haguvara S.
, and
Eguchi S.
, J. Org. Chem. 1991 , 56 , 1535 .
17.
(a)
Von Niementowski S.
, J. Prakt. Chem. 1895 , 51 , 564 .
18.
Gotthelf P.
, and
Bogert M. T.
, J. Am. Chem. Soc. 1901 , 23 , 611 .
19.
Endicott M.M.
,
Wick E.
,
Mercury M. L.
, and
Sherrill M.
, J. Am. Chem. Soc. 1946 , 68 , 1299 .
