The Synthesis of N,S-Substituted compounds from the reactions of 2-Nitrohalobuta-1,3-diene with Mercaptocoumarin

Abstract

4-Bromo-1,3,4-trichloro-2-nitro-1-(7-coumarinthio-4-methyl)-1,3-butadiene (3), and 4-Bromo-3,4-dichloro-2-nitro-1,1-bis (7-coumarinthio-4-methyl)-1,3-butadiene (4) were synthesized from the reactions of 4-bromo-1,1,3,4-tetrachloro-2-nitro-1,3-butadiene (1) with 7-mercapto-4-methylcoumarin (2). Afterwards, new N,S- substituted dienes( 6a-j, 8a-d, 10 and 12) were obtained by the reactions of derivatives of piperazine [4-(fluorophenyl) piperazine, phenyl piperazine, 1-(2-methoxyphenyl)-piperazine, ethoxycarbonyl piperazine, formylpiperazine,2-(fluorophenyl)-piperazine, 4-(nitrophenyl)-piperazine, diphenylmethyl piperazine, 4-(hydroxyphenyl)- piperazine, 4-(hydroxyphenyl)- piperazine]; piperidine [4-methyl piperidinyl, 4-benzyl piperidinyl, 4-hydroxy piperidinyl]; morpholin and 1,4-dioxoazospiro [4,5] decan with the mono(thio)substituted nitrodien compound 3. Structures of the novel compounds were characterized by using microanalysis, FT-IR, UV-Vis, 1H-NMR, APT and MS spectroscopy methods.