<原報>Thiazoline および Thiazolidine 誘導体の合成〔X〕 : 3-(Alkylthiocarbamoyl)-2-iminothiazolidines, 3-(Alkylthiocarbamoyl)-2-oxothiazolidines, 2-Alkylthioureido-2-thiazolines の合成

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概要

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• Synthesis of 3-Alkylthiocarbamoyl-2-iminothiazolines [III], 2-Alkylthioureido-2-thiazolines [IV] and 3-Alkylthiocarbamoyl-2-oxothiazolines [VI] were studied by several methods shown in Chart I. In method [A], treatment of 2-Aminothiazoline [I] with Alkylisocyanate [II] gave the main product [III] with some amount or isomeric one [IV], and they can be separated by chromatography. [III] converted into [IV] by heating in Benzene or Pyridine. [VI] was also obtained by the hydrolysis of [III] in 15% H_2SO_4 aq. solution at 96-97℃. As shown in Table I, identification of these compounds were made by Urtraviolet (UV) absorption spectrum and Infrared (IR) absorption spectrum. Data of Mass spectrum (MS) and Elemental analysis supported this results. On the TLC, Rf values of [III] and [VI], having 3-thiocarbamoyl group, are higher than that of [IV]. Using these Rf values [III], [VI], and [IV] can be distinguished. In the method [B], treatment of Alkyldithiobiuret [VII] with 1,2-Dibromoethane in ethanol solution gave [III]. The NMR spectral date of [IIIa, b], [IVa, b], and [VIa, b] in CD(Cl)_3 are summarized Table II, and also the spectra of [IIIb, IVb, VIb] are shown in Fig. I, II, III. As expected, the signals of methylene group (C^4) of thiazolidine having thiocarbonyl group at the ring nitrogen atom [IIIa, b], [VIa, b] appear at a lower field than those of the corresponding methylene group of [IVa, b]. The chemical shift differences of the proton signals attaching to nitrogen atom between 3-methyl-2-iminothiazolidine and 2-amino-2-thiazoline [I] are not so marked, indicating that imino or amino structures have little effect on the chemical shifts of their protons. However, the proton signals attaching to nitrogen atom of [IIIa, b] shifted about 2 ppm more to downfield than those [I] and 3-methyl-2-iminothiazolidine. This deshielding effect should be due to the substitution of thiocarbonyl group at ring nitrogen.

• 共立薬科大学の論文
• 1973-12-25

著者

• 与田 玲子

  共立薬科大学

• 山本 有一

  Kyoritsu College of Pharmacy

関連論文

• キャピラリー電気泳動によるアスピリン軟膏中のアスピリンの迅速定量
• Synthesis and Properties of ω-Aminooxyalkyliminodiacetic Acids, Bifunctional Chelating Agents for Carbonyl Labeling
• Preparation of 2-Aminooxyethyliminodiacetic Acid, a Bifunctional Chelating Agent for Carbonyl Labeling
• Solvolysis of Pyridoxal Hydrochloride in Alcohols
• Palladium (II) Chelates of 1,1-Dimethyl-3-(4-methyl-2-thiazolyl) thiourea and Related Thioureas
• Products of the Nitration of 2-Thiazolylureas and 2-Thiazolylthioureas
• 新有機試薬N,N-ジメチル-N'-(4-フェニル-2-チアゾリル)チオ尿素によるパラジウムの吸光光度定量法
• Proton-Induced Ring Transformation of 2-Imino-3-thiocarbamoyl-4-thiazoline
• 3-(N, N-Dimethylthiocarbamoyl)-2-alkyl(or phenyl)imino-4-methylthiazole の転位反応(その 2)
• 3-(N, N-Dimethylthiocarbamoyl)-2-alkyl (or phenyl) imino-4-methylthiazole の転位反応
• Thiazole 誘導体の研究 (VI) : 2-Dialkylthioureidothiazole の合成
• チオウレイド誘導体に関する分析化学的研究 I : スクリーニングテスト(66 種金属イオン)
• Studies on Thiazole and Thiazoline Derivatives XII : Synthesis of 2-Carbamoyl, 2-(N-alkylcarbamoyl) and 2-(N-alkylthiocarbamoyl)-3,4-dimethyl-4-thiazoline
• N-(2-Thiazolyl) thioureas and Their Copper (II) Chelates. Molecular Species in Solution
• Pyrolytic S→N Methyl Migration of N, N-Dimethyl-N'-(4-methyl-2-thiazolyl)-S-methylisothiourea
• (2-thiazolyl) urea および thiourea 誘導体のニトロ化について
• N, N-Dialkyl-N'-(3-alkyl or 3,4-dialkylthiazolyl-2)-S-methylisothiourea の methyltrasfer について
• N, N-Dimethyl-N'-(4-phenyl-2-thiazolyl) thiourea の誘導体について
• 新有機試薬 1,1-ジメチル-3-(4-フェニル-2-チアゾリル)チオウレアによるパラジウムの定量法
• Thiazolidine-2-one (1) と N, N-Dimethylthiocarbamoylchloride (2) との反応による Unusual Product
• Studies on Thiazole and Thiazoline Derivatives (XVII) : Methylation of N-Alkyl (or N, N-dialkyl)-N'-(2-thiazolyl) thiourea derivatives
• 2-Aminothiazole, 2-Methylaminothiazole 及び 2-Thiazoline 誘導体と N, N-Dimethylthiocarbamoyl chloride の反応について
• N, N-Dimethyl-2,4-dithiobiuret とα-haloketone による 2,5'-bithiazole 誘導体の one step synthesis について
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• Studies on Thiazoline Derivatives (XVI) : Synthesis of N-Alkyl-N'-cyano-N"-(3,4-dimethyl-4-thiazoline-2-ylidene) guanidine
• Studies on Thiazoline Derivatives (XV) : Reactions of 2-Phenyl and 2-Methylamino-2-thiazolines with Methyl and Phenylisothiocyanates
• Thiazole 誘導体の研究〔VII〕 2-Dialkylthioureido-thiazols 誘導体の合成
• Thiazole誘導体の研究2-Alkylureidothiazoleの合成
• Thiazole 誘導体の研究 2-Laurylamino-4-methyl thiazole の合成
• Thiazole 誘導体の研究 (II) : 2-Phenylthioureido-4-methylthiazole の無水酢酸による分解反応等について
• 2-Amino-2-thiazoline 及び 2-Imino-3-methylthiazolidine 等と CS_2 の反応について
• The Structure of Pd Complexes of 2-(N-methylthiocarbamoyl) amino-4-methyl-thiazole and 2-(N, N-dimethylthiocarbamoyl) amino-4-methylthiazole
• 2-Amino-2-thiazoline 及び 2-Methylamino-2-thiazoline と N, N-dimethylthiocarbamoyl chloride の反応について
• Oxazoline および Oxazolidine 誘導体の合成
• 2-(N-Alkyl (or Aryl) thiocarbamoyl) alkylamino-4-alkylthiazole の熱転位反応について
• 2-thiocarbamoylaminothiazole 誘導体のPd錯体の構造
• Thiazoline 及び Thiazolidine 誘導体の合成 XIII : 2-Imino-3-methylcarbamoylthiazolidine 及び関連化合物の合成
• Studies on Thiazoline and Thiazolidine Derivatives. XI. Synthesis of 3-N-Alkylthiocarbamoyl-2-alkyliminothiazolidines
• 3-N-Alkylthiocarbamoyl-2-Alkyliminothiazolidines 誘導体の合成
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• Thiazoline および Thiazolidine 誘導体の合成〔X〕 : 3-(Alkylthiocarbamoyl)-2-iminothiazolidines, 3-(Alkylthiocarbamoyl)-2-oxothiazolidines, 2-Alkylthioureido-2-thiazolines の合成
• Thiazolidine 誘導体の研究〔IX〕 : 3-Thiocarbamoyl-2-iminothiazolidine, 3-Thiocarbamoyl-2-oxothiazolidine, 2-(Alkylthiocarbamoylimino)-3-methylthiazolidines の合成
• Thiazole 誘導体の研究〔VIII〕 : 2-Thioureidothiazole 誘導体の合成
• Thiazole 誘導体の研究 (V) : チアゾール環を有する Alkylthioethers の合成
• 環境応答性高分子を用いたHPLC用充填剤

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