Abstract
The reaction of 1,4-naphthoquinone with a mixture of urea and ethylcyanoacetate in ethanol containing a piperidine catalyst afforded compound
1
, which reacted with acetonitrile and steam of hydrogen chloride to yield compound 2, which readily condensed with different aromatic amine to give
3a-c
. Compound
3a-c
reacted with chloroacetyl chloride and/or mercaptoacetic acid to give spiro β-Lactam
4a-c
, and spiro thiazolidinone
5a-c
also isolated β-Lactam and thiazolidinone
7a-d
and
8a-d
prepared from a reaction of isolated schiff base
6a-d
with chloroacetyle chloride and mercaptoacetic acid. Compound
2
reacted with ethyl iodide to give compound
9
, which used to synthesis of new shiff bases
10a-c
and
13a-d
. The new schiff bases
10a-c
and
13a-d
reacted with chloroacetyl chloride or mercaptoacetic acid to give B-Lactams
11a-c
and
14a-d
and thiazolidinone derivatives
12a-c
and
15a-d
.