Ethyl 5-pyrrolidin-1-ylthiadiazole-4-carboxylate | 342782-49-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: Ethyl 5-pyrrolidin-1-ylthiadiazole-4-carboxylate
• CAS: 342782-49-4
• 化学式: C₉H₁₃N₃O₂S
• 分子量: 227.287
• InChiKey: LQRWEAFUQHOWRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  83.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Ethyl 5-pyrrolidin-1-ylthiadiazole-4-carboxylate 在 manganese(IV) oxide 、 sodium tetrahydroborate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (1-Benzyl-1H-[1,2,3]triazol-4-yl)-pyrrolidin-1-yl-methanethione
  参考文献：
  名称：

  Reactions of 5-dialkylamino-1,2,3-thiadiazole-4-carbaldehydes with amines as a method for the synthesis of 1,2,3-triazole-4-carbothioamides

  摘要：

  A method for the synthesis of previously inaccessible 5-dialkylamino-substituted 1,2,3-thiadiazole-4-carbaldehydes was developed. Ring transformation in these compounds induced by primary aliphatic and aromatic amines, hydroxylamines, and N-substituted hydrazines resulted in the synthesis of a broad range of 1,2,3-triazole-4-carbothioamide.

  DOI：

  10.1023/b:rucb.0000042292.19119.3d
• 作为产物：
  描述：

  四氢吡咯 、 5-氯-1,2,3-噻二唑-4-羧酸乙酯 以 乙醇 为溶剂， 反应 0.5h， 以47%的产率得到Ethyl 5-pyrrolidin-1-ylthiadiazole-4-carboxylate
  参考文献：
  名称：

  Reactions of 5-dialkylamino-1,2,3-thiadiazole-4-carbaldehydes with amines as a method for the synthesis of 1,2,3-triazole-4-carbothioamides

  摘要：

  A method for the synthesis of previously inaccessible 5-dialkylamino-substituted 1,2,3-thiadiazole-4-carbaldehydes was developed. Ring transformation in these compounds induced by primary aliphatic and aromatic amines, hydroxylamines, and N-substituted hydrazines resulted in the synthesis of a broad range of 1,2,3-triazole-4-carbothioamide.

  DOI：

  10.1023/b:rucb.0000042292.19119.3d

文献信息

• The effect of the C5-substituent on regioselectivity in the Rh(<scp>i</scp>)-catalyzed intermolecular transannulation of 1,2,3-thiadiazoles with phenylacetylene
  作者：Marina A. Tokareva、Indrek Pernik、Barbara A. Messerle、Tatiana V. Glukhareva、Sinead T. Keaveney

  DOI：10.1039/d3cy00290j

  日期：——

  Despite the growing use of denitrogenative reactions of 1,2,3-thiadiazoles in heterocycle synthesis, the origin of the varied reactivity and divergent regioselectivity observed in their transannulation reactions is not well understood. To address this limitation, systematic studies on the reactivity and regioselectivity in the Rh(I)-catalyzed intermolecular transannulation between a range of substituted

  尽管在杂环合成中越来越多地使用 1,2,3-噻二唑的脱氮反应，但在它们的环化反应中观察到的不同反应性和不同的区域选择性的起源尚不清楚。为了解决这一局限性，对 Rh( I)-催化的一系列取代的 1,2,3-噻二唑和苯乙炔之间的分子间环化反应已经进行。我们的实验数据表明，1,2,3-噻二唑环上 C5-取代基的电子性质显着影响反应性。此外，取代基的性质对反应的区域选择性有显着影响，供电子基团产生 2,3,4- 取代的噻吩，强吸电子基团有利于 2,3,5-替代产品。使用密度泛函理论计算支持和合理化确定的实验趋势。
• Reactions of 5-dialkylamino-1,2,3-thiadiazole-4-carbaldehydes with amines as a method for the synthesis of 1,2,3-triazole-4-carbothioamides
  作者：T. V. Glukhareva、Yu. Yu. Morzherin、L. V. Dyudya、K. V. Malysheva、A. V. Tkachev、A. Padva、V. A. Bakulev

  DOI：10.1023/b:rucb.0000042292.19119.3d

  日期：2004.6

  A method for the synthesis of previously inaccessible 5-dialkylamino-substituted 1,2,3-thiadiazole-4-carbaldehydes was developed. Ring transformation in these compounds induced by primary aliphatic and aromatic amines, hydroxylamines, and N-substituted hydrazines resulted in the synthesis of a broad range of 1,2,3-triazole-4-carbothioamide.