Gökşin Aydinli

New N,S-Substituted Dienes from the Reactions of Some Aliphatic Mono(thio)substituted Nitrodienes with Aromatic Primary Amines and Cyclic Amines

Reaction of 2-nitropentachlorobutadiene with thiols and amines gave new N,S- and S,S-substituted nitrodiene compounds is discussed.

The Synthesis of New S- and N,S-Substituted Halo Nitro Dienes by the Reactions of 1-Bromo-1,2,4,4-tetrachloro-3-nitrobuta-1,3-diene with Thiols and Cyclic Amines

The substituted products alkyl(aryl)thio-tetrahalo-3-nitrobuta-1,3-dienes 3a–b were obtained from the reactions of 1-bromo-1,2,4,4-tetrachloro-3-nitrobuta-1,3-diene (1) with thiols. Further reactions of the substituted product alkyl(aryl)thio-tetrahalo-3-nitrobuta-1,3-dienes 3a–b in dichloromethane reacted with piperazine derivatives and morpholine to generate 5a–b and 7a–l. The structures of the new compounds were determined by microanalysis and spectroscopic data.

DIE SYNTHESE VON EINIGEN NEUEN S-, S,S- UND N,S-SUBSTITUIERTEN 1,3-HALONITRODIENEN

Abstract Mono(thio)substituted butadiene compounds 3a-c are prepared by mixing 2-nitropentachlo-robutadiene (1) with thiols (2a-c). 2-Nitrodiene 1 gives bis(thio)substituted 4a and 4d by the reaction with the same thiols in EtOH containing sodium hydroxide. N,S-Substituted 1,3-butadienes 6a-h were obtained by the reactions of 3a-c with primary amines. S-Substituted nitrodiene compounds 3a-c give 8a-c and 10a-c by the reaction with piperazines 7 and 9 in ether. Die Mono(thio)substituierten Butadien-Verbindungen 3a-c werden durch Umsetzung von 2-Nitropentachlorobutadiene (1) mit Thiolen (2a-c) präpariert. Bei der Reaktion von 2-Nitrodiene 1 mit denselben Thiolen in EtOH entstehen bis(thio)-substituierte 4a und 4d. N,S-Substituierte 1,3-Butadienen 6a-h sind durch Umsetzung von 3a-c mit primären Aminen gewonnen worden. S-Substituierte Nitrodienverbindungen 3a-c geben bei der Reaktion mit den Piperazinen 7 und 9 in Ether 8a-c und 10a-c.

Crystal Structures of 4-Methyl-1-(3,4,4-trichloro-1-cyclohexylsulfanyl-2-nitro-buta-1,3-dienyl) Piperidine and 4-(3,4,4-Trichloro-1-decylsulfanyl-2-nitro-buta-1,3-dienyl) Morpholine and Spectroscopic Properties

ABSTRACT 4-Methyl-1-(3,4,4-trichloro-1-cyclohexylsulfanyl-2-nitro-buta-1,3-dienyl) piperidine (2a) and 4-(3,4,4-trichloro-1-decylsulfanyl-2-nitro-buta-1,3-dienyl) morpholine (3b) were synthesized, and their crystal structures were determined. The compound 2a is monoclinic, with space group P21/n, a = 13.2874(8), b = 9.7584(4), c = 15.9479(9) Å, β = 109.110(3)°. V = 1953.91(18) Å3, Z = 4. The cyclohexyl and piperidine rings adopt chair conformation. The compound 3b is monoclinic, with space group P 1 21/c 1, a = 15.7741(3), b = 8.9335(10), c = 16.7775(4) Å, β = 100.7382(13)°. V = 2322.85(8)Å3, Z = 4. The morpholine ring is in a chair conformation. The butadiene unit assumed a configuration close to cissoid in both structures, and their spectroscopic properties were investigated.

Novel N,S- and S,S-Substituted Dienes Synthesized from Mercapto Triazole and Some Amine Derivatives

2-Nitrodiene 1 reacted with 3-mercapto-1,2,4-triazole and cyclohexyl thiol to yield compounds 3 and 4 , respectively. Compounds 7a – d were obtained by reactions of 6a – d with 2 . The novel N,S-substituted dienes 9a – c were obtained by treatment of compound 6b with the piperazine derivatives 8a–c . Compound 6b was reacted with 10 to give compound 11 as a new morpholine derivative. Compound 6b gave a new monobutadienyl homopiperazine 13 when reacted with homopiperazine in methylene chloride. Compound 4 was structurally characterized by single-crystal X-ray diffraction.

Mono-, Bis- and Tris (Thio) Substituted Nitrobutadienes from 2-Nitrodiene with 7-Mercapto-4-Methyl Coumarin and N,S-Substituted Dienes from Mono(Thio)-Substituted Dienes with Amines

Thiosubstituted nitrodien compounds 3a and 4a were prepared by mixing compound 1 with thiol 2a. 1 gave 5a by the reaction with coumarin derivative 2a in EtOH containing sodium hydroxide. Mono(thio)substituted diene compound 3 reacted with 10 and 12 and yielded 11 and 13 in CH2Cl2. 7a–h and 9a–d were obtained by the reactions of 6a–h and 8a–d with compound 3a.

SOME NEW S-, S,S- AND N,S-SUBSTITUTED 2-NITRODIENES AND BUTADIENYL-SUBSTITUTED PIPERAZINES

Nitrodiene 1 reacted with 2a, b and gave the novel compounds 3a, b, 4a, b, and 5a. Monosubstituted diene compound 3a gave the compounds 9a with morpholine, 11a with piperidine, and 13a with homopiperazine. Compound 3a gives the thioether compound 15 by the reaction with the dithiol (HS─(CH2)2─O─(CH2)2─SH) in ethanol containing sodium hydroxide.

2,4,4-Tris(benzyl-sulfan-yl)-1,1-dichloro-3-nitro-buta-1,3-diene.

In the title compound, C25H21Cl2NO2S3, the three phenyl rings are inclined to each other at dihedral angles of 68.4 (1), 79.5 (1) and 37.0 (1)°.

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.