Some new N,S-substituted 2-nitrodiene compounds from relations of mono(p-fluorarylthio)substituted dienes with amines

Abstract

2-Nitrodiene compound 1 was stirred with p-fluorothiophenol for a long time and compound 3 was obtained. Compound 1 gave bis(thio)substituted 2-nitrodiene compound 4 and tris(thio)substituted compound 5 with 2 moles of p-fluorothiophenol in the presence of NaOH in ethanol. The compounds 9a-g have been prepared from 8a-g and 3. Compound 7 was obtained from the reaction of mono(thio)substituted 2-nitrodiene with morpholine. Compound 3 gives 11a-d in the reaction with piperidines in CH2Cl2 (or ether). Compound 13a-b have been obtained from the reaction of compound 3 with primary amines 12a-b. Compound 3 gives 15 and 16 in the reaction with 2,5dimethylpiperazine in CH2Cl2.