ethyl 2-chloro-3-oxo-3,4-dihydro-2H-1,4-benzothiazin-2-carboxylate | 742062-60-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: ethyl 2-chloro-3-oxo-3,4-dihydro-2H-1,4-benzothiazin-2-carboxylate
• 英文别名: 2-Chloro-2-ethoxycarbonyl-4h-benzo[1,4]thiazine-3-one；ethyl 2-chloro-3-oxo-4H-1,4-benzothiazine-2-carboxylate
• CAS: 742062-60-8
• 化学式: C₁₁H₁₀ClNO₃S
• 分子量: 271.724
• InChiKey: NZBNRBGWQYMMAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-chloro-3-oxo-3,4-dihydro-2H-1,4-benzothiazin-2-carboxylate 在 盐酸 、 一水合肼 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 6.5h， 生成 N,N'-[dithiobis(2,1-phenylene)]bis(3-oxo-2,3,5,6,7,8-hexahydrocinnoline-4-carboxamide)
  参考文献：
  名称：

  New 2-functionalized 2H-3,4-dihydro-1,4-benzothiazin-3-ones and their application in the synthesis of spiro heterocycles

  摘要：

  The reaction of 2-chloro-3,4-dihydro-2H-1,4-benzothiazin-3-ones 1 with enamines is an efficient synthetic method to produce 2-substituted derivatives. The resulting bifunctional compounds such as 6a, b, 7c, d and 8b react with hydrazines to furnish the spiro derivatives of N-aminopyrrole or 3-pyridazinone depending on the direction of the primary nucleophilic attack and the nature of the nucleophile. Under the reaction conditions, spiro pyridazinones 13 are converted into the 3-pyridazinone-4-carboxylic acid derivatives 9 via the 1,4-thiazine ring opening. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.04.084
• 作为产物：
  描述：

  3-Oxo-3,4-dihydro-2H-1,4-benzothiazin-2-carbonsaeure-ethylester 在 磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以85%的产率得到ethyl 2-chloro-3-oxo-3,4-dihydro-2H-1,4-benzothiazin-2-carboxylate
  参考文献：
  名称：

  2-Hetaryl Derivatives of 3-Oxo-3,4-dihydro-2H-1,4-benzothiazine

  摘要：

  描述了一种合成3-氧-3,4-二氢-2H-1,4-苯并噻嗪的2-杂芳衍生物的新方法。2-氯衍生物2a和2b在碱性催化（略微过量的三乙胺）下与富电子的杂环化合物3-14反应，得到取代产物16-36。在2b与14和15的反应中，氨基和乙氧基羧基之间发生了分子间环化，分别生成了螺旋化合物35和36。

  DOI：

  10.1055/s-2004-822375

文献信息

• Synthesis of 1,4-benzothiazin-2-yl derivatives of 1,3-dicarbonyl compounds and benzothiazinone spiro derivatives by the reaction of 2-chloro-1,4-benzothiazin-3-ones with ‘push–pull’ enamines
  作者：Konstantin G. Nazarenko、Nataliya A. Shtil、Sergey A. Buth、Alexander N. Chernega、Miron O. Lozinskii、Andrey A. Tolmachev

  DOI：10.1016/j.tet.2008.02.049

  日期：2008.5

  The reaction of 2-chloro-3-oxo-3,4-dihydro-2H-1,4-benzothiazines with ‘push–pull’ enamines was investigated. The reaction with the enamines occurs at the β-carbon atom in the presence of a small excess of triethylamine. As a result, a set of 3-oxo-3,4-dihydro-2H-1,4-benzothiazin-2-yl derivatives of 1,3-dicarbonyl compounds and benzothiazinone spiro derivatives was prepared. On acidic hydrolysis of

  研究了2-氯-3-氧代-3,4-二氢-2 H -1,4-苯并噻嗪与“推挽”烯胺的反应。在少量过量的三乙胺存在下，与烯胺的反应发生在β-碳原子上。结果，制备了一组1，3-二羰基化合物的3-氧代-3，4-二氢-2 H -1，4-苯并噻嗪-2-基衍生物和苯并噻嗪酮螺衍生物。在对2-乙基-3-（甲基亚氨基）-2-（3-氧代-3,4-二氢-2 H -1,4-苯并噻嗪-2-基）丁酸乙酯进行酸性水解后，得到了新的重排结构，得到乙基11-发现了-2,3-二甲基-4-氧代-2,3,4,5-四氢-1 H -2,5-甲基-6,1,3-苯并噻二唑并辛基-11羧酸乙酯。讨论了可能的反应机理和影响反应过程的因素。
• 2-Hetaryl Derivatives of 3-Oxo-3,4-dihydro-2<i>H</i>-1,4-benzothiazine
  作者：Konstantin G. Nazarenko、Nataliya A. Shtil、Alexander N. Chernega、Miron O. Lozinskii、Andrey A. Tolmachev

  DOI：10.1055/s-2004-822375

  日期：——

  A new approach for the synthesis of 2-hetaryl derivatives of 3-oxo-3,4-dihydro-2H-1,4-benzothiazines is described. 2-Chloro derivatives of 2a,b were reacted with electron-rich heterocycles 3-14 under basic catalysis (with a slight excess of Et3N) to provide the substitution products 16-36. In the reaction of 2b with 14 and 15, an intermolecular cyclization took place between the amino and ethoxycarbonyl groups, resulting in spiro compounds 35 and 36, respectively.

  描述了一种合成3-氧-3,4-二氢-2H-1,4-苯并噻嗪的2-杂芳衍生物的新方法。2-氯衍生物2a和2b在碱性催化（略微过量的三乙胺）下与富电子的杂环化合物3-14反应，得到取代产物16-36。在2b与14和15的反应中，氨基和乙氧基羧基之间发生了分子间环化，分别生成了螺旋化合物35和36。
• New 2-functionalized 2H-3,4-dihydro-1,4-benzothiazin-3-ones and their application in the synthesis of spiro heterocycles
  作者：K.G. Nazarenko、N.A. Shtil、M.O. Lozinskii、A.A. Tolmachev

  DOI：10.1016/j.tet.2007.04.084

  日期：2007.8

  The reaction of 2-chloro-3,4-dihydro-2H-1,4-benzothiazin-3-ones 1 with enamines is an efficient synthetic method to produce 2-substituted derivatives. The resulting bifunctional compounds such as 6a, b, 7c, d and 8b react with hydrazines to furnish the spiro derivatives of N-aminopyrrole or 3-pyridazinone depending on the direction of the primary nucleophilic attack and the nature of the nucleophile. Under the reaction conditions, spiro pyridazinones 13 are converted into the 3-pyridazinone-4-carboxylic acid derivatives 9 via the 1,4-thiazine ring opening. (c) 2007 Elsevier Ltd. All rights reserved.