The coumarin-3-cinnamoyl derivatives
2a-d were prepared via Claisen-Schmidt condensation of 3-acetylcoumarin
1 with different aromatic aldehydes. Cycloaddition reaction of
2b,e with guanidine and thiourea yielded the corresponding aminopyrmimidine
3a,b and thioxypyrimidine derivatives
4a,b, respectively. Compounds
4a,b were condensed with chloroacetic acid or 3-bromopropionic
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The coumarin-3-cinnamoyl derivatives
2a-d were prepared via Claisen-Schmidt condensation of 3-acetylcoumarin
1 with different aromatic aldehydes. Cycloaddition reaction of
2b,e with guanidine and thiourea yielded the corresponding aminopyrmimidine
3a,b and thioxypyrimidine derivatives
4a,b, respectively. Compounds
4a,b were condensed with chloroacetic acid or 3-bromopropionic acid to yield coumarin 3-thiazolo-pyrimidine
5a,b and thiazinopyrimidine
6a,b derivatives, respectively. Compounds
4a,b were condensed with chloroacetic acid and aromatic aldehyde to yield the aryl methylene derivatives
7a,b which could be prepared directly by condensation of compounds
5a,b with aromatic aldehydes. Compounds
2a-e were condensed with malononitrile or ethyl cyano acetate in presence of ammonium acetate to yield cyanopyridine
8a,b and cyanopyridone
9a-d derivatives, respectively, which were prepared by condensation of 3-acetylcoumarin
1, malononitrile or ethylcyanoacetate and aromatic aldehydes in presence of ammonium acetate. Condensation of compounds
2a,b,e with o-phenylenediamine in refluxing ethanol led to the formation of
10a-c as intermediate, followed by cleavage by thermolysis to benzimidazole derivative
11 along with compounds
12a-c as mixture, which were obtained directly by fusion of a,&unsaturated ketones
2 with ophenylene diamine at 200-220°C, while compound
11 could be prepared in pure form by fusion of
1 with o-phenylene diamine at the same temperature. The pharmacological screening showed that many of these obtained compounds have good antidepressant activity comparable to Tranylcypromine® as reference drugs.
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