ethyl 2-dimethylaminothiazole-5-carboxylate | 75427-05-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 2-dimethylaminothiazole-5-carboxylate
• 英文别名: Ethyl 2-(dimethylamino)thiazole-5-carboxylate；ethyl 2-(dimethylamino)-1,3-thiazole-5-carboxylate
• CAS: 75427-05-3
• 化学式: C₈H₁₂N₂O₂S
• 分子量: 200.261
• InChiKey: FSYRFLKQQXNKDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  70.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  溴乙酸乙酯 、 N,N-Dimethyl-N'-(dimethylamino-thiocarbonyl)-formamidin 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以81%的产率得到ethyl 2-dimethylaminothiazole-5-carboxylate
  参考文献：
  名称：

  Orthoamide. IL. Umsetzungen von Orthoamid-Derivaten mit Schwefel und Selen, Synthesen von 1,3-Thiazol- und 1,3-Selenazolderivaten

  摘要：

  N,N-Dimethylformamide acetal reacts with elemental selenium to give a mixture of selenocarbonic acid derivatives 2 and 3, which can be converted to the pure N,N-dimethylcarbamidic acid Se-methylester 2 by treatment with methyl iodide. Analogously from the orthoformic acid derivatives 5 and 6 and selenium the N,N,N',N'-tetramethyl-selenurea 7 can be prepared. In the reaction of 12 with elemental sulfur and selenium the amidines 14 and 15, respectively, are formed. By treatment of 14 and 15 with alpha-halogenated carbonyl compounds and triethylamine the 1,3-thiazoles 18 and 1,3-selenazoles 19 can be prepared. The synthesis of the propynoic acid orthoamide 26b is described. 26b reacts with the guanidinium salt 24b to give the bis-orthoamide of butynedioic acid 20b. Other orthoamides of butynedioic acid 20b-20e can be synthesized from the orthoamide 20a by transamination. The thiolation of the orthoamides affords the bis-amidinium-dithiolates 21a-c, which can be alkylated to give the bis-amidinium salts 27. By treatment with alpha-halogene carbonyl compounds and triethylamine the dithiolates 21a-e are cyclized to give thieno [3,2b] thiophenes 28a-n. The quadrupoles 21 undergo cycloadditions with dimethyl-butynedioate which afford the bis(3H-thiophene-2 ylidenes) 29a-c. Treatment of 29a with methyl tosylate gives rise to the dithiophene 30a. The dithiophene 30b can be obtained by heating 21b with dimethylbutynedionate.

  DOI：

  10.1002/prac.19963380180

文献信息

• Convenient Synthesis of 2,3-Dihydro-1,2,4-thiadiazoles, 4,5-Dihydro-1,3-thiazoles, and 1,3-Thiazoles through a [4+1]-Type Oxidative Ring Closure of 1,3-Thiaza-1,3-butadienes
  作者：Kazuaki Shimada、Megumi Isogami、Kitami Maeda、Rei Nishinomiya、Toshinobu Korenaga

  DOI：10.3987/com-20-14244

  日期：——

  1,3-Thiaza-1,3-butadienes bearing an N,N-dimethylamino group at the C-2 position were efficiently converted into 5H-1,2,4-oxathiazoles, 2,3-dihydro-1,2,4-thiadiazoles, 4,5-dihydro-1,3-thiazoles, and 1,3-thiazoles through an oxidative ring closure by treating with mCPBA, chloramine-T, metal carbenoids, or dichlorocarbene, respectively, via the ring closure of in situ generated heterocumulene-type reactive species involving thione S-oxides, thione S-imides, and thiocarbonyl ylides.
• Kaye, Perry T.; Meakins, G. Denis; Smith, Anthony K., Journal of the Chemical Society. Perkin transactions I, 1983, # 8, p. 1677 - 1680
  作者：Kaye, Perry T.、Meakins, G. Denis、Smith, Anthony K.、Tirel, Malcolm D.

  DOI：——

  日期：——
• KAYE, P. T.;MEAKINS, G. D.;SMITH, A. K.;TIREL, M. D., J. CHEM. SOC. PERKIN TRANS., 1983, N 8, 1677-1680
  作者：KAYE, P. T.、MEAKINS, G. D.、SMITH, A. K.、TIREL, M. D.

  DOI：——

  日期：——