The Novel N,S-Substituted Halonitrodienes from the Reactions of Thiosubstituted Nitrodiene with Piperazine and Morpholine

The substituted 1,2-dibromomethanethio nitrodiene 2 was obtained from the addition of bromine to S-substituted nitrodien 1 in carbon tetrachloride. N, S-substituted compounds 4a–h were synthesized from the reactions of compound 2 with several substituted piperazine derivatives 3a–h in dichloromethane. N, S-substituted compounds 6 and 8 were synthesized from the reaction of 2 with morpholine ( 5 ) and thiomorpholine ( 7 ) in dichloromethane, respectively. Dibutadienyl piperazines 10 , 12 , and 14 were synthesized from the reactions of 2 with homopiperazine ( 9 ), piperazine ( 11 ), and 2,5-dimethylpiperazine ( 13 ), respectively.     

DIBUTADIENYL PIPERAZINE,DIBUTADIENYL HOMOPIPERAZINES AND BUTADIENYL-SUBSTITUTED PIPERIDINES FROM MONOSUBSTITUTED HALODIENES

Compounds 3a–k were obtained from the reactions of compounds 1a–k with homopiperazine (2) in CH ₂ Cl ₂ . Compounds 1a–b, 1d–f, and 1h–l gave compounds 5a–b, 5d–f, and 5h–l with 2-methylpiperazine (4) in dichloromethane. Compounds 7c and 9c were obtained from the reactions of compound 1c with 4-ethoxycarbonyl piperazine (6) and 4-piperidinol (8) in CH ₂ Cl ₂ . Compounds 1a and 1f gave compounds 11a and 11f with 4-methylpiperazine (10), and compound 13f was obtained from the reactions of compound 1f with 4-methylpiperidine (12) in CH ₂ Cl ₂ .     

New N,S-Substituted Dienes from Mono(thio)substituted-2-nitrohalo-1,3-diene and Some Amines

Mono(thio)substituted nitrodiene compound 1 reacted with 2a–f and yielded 3a–f in methylene chloride. Compound 1 gave 7 by the reaction with 6. Compounds 5a–c were obtained by the reactions of 4a–c with 1. 3a also has been structurally characterized using single-crystal X-ray diffraction analyses.