2-formylamino-thiazole-5-carbonitrile | 51640-42-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-formylamino-thiazole-5-carbonitrile
• 英文别名: 5-cyano-2-formamidothiazole；2-Formamidothiazol-5-carbonitril；N-(5-cyano-1,3-thiazol-2-yl)formamide
• CAS: 51640-42-7
• 化学式: C₅H₃N₃OS
• 分子量: 153.164
• InChiKey: ZJHORDRXUABFKF-UHFFFAOYSA-N

物化性质

• 沸点：
  342.6±34.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  94
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-formylamino-thiazole-5-carbonitrile 在 盐酸 作用下， 以 乙醇 为溶剂， 以88%的产率得到2-氨基-5-氰基噻唑
  参考文献：
  名称：

  Phenyl thiazolyl urea and carbamate derivatives as new inhibitors of bacterial cell-wall biosynthesis

  摘要：

  Over 50 phenyl thiazolyl urea and carbamate derivatives were synthesized for evaluation as new inhibitors of bacterial cell-wall biosynthesis. Many of them demonstrated good activity against MurA and MurB and gram-positive bacteria including MRSA, VRE and PRSP. 3,4-Difluorophenyl 5-cyanothiazolylurea (3p) with clog P of 2.64 demonstrated antibacterial activity against both gram-positive and gram-negative bacteria. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.082
• 作为产物：
  描述：

  甲酸 、 2-氨基-5-醛基噻唑 在 盐酸羟胺 、 sodium formate 作用下， 生成 2-formylamino-thiazole-5-carbonitrile
  参考文献：
  名称：

  一些2-硝基噻唑

  摘要：

  用三氟乙酸酐或光气和环氧丙烷将2-硝基噻唑-5-甲醛甲醛（1）脱水，得到腈（2），该腈已转化为3-（2-硝基噻唑-5-基）-1,2 ，4-恶二唑（4）。肟（1）被乙酸酐转化为2-乙酰氧基噻唑-5-腈（5），亚硫酰氯转化为2-氯噻唑-5-腈（6）。3-（2-氨基噻唑-5-基）-1,2,4-恶二唑（7）在铜存在下与亚硝酸反应生成硝基化合物（4）和脱氨基化合物3-（噻唑-5-基）-1，2，4-恶二唑（8）。已经观察到一些类似的脱氨基。

  DOI：

  10.1039/p19730002769

文献信息

• Some 2-nitrothiazoles
  作者：Alan D. Borthwick、Michael W. Foxton、Brian V. Gray、Gordon I. Gregory、Peter W. Seale、Willam K. Warburton

  DOI：10.1039/p19730002769

  日期：——

  3-(2-Aminothiazol-5-yl)-1,2,4-oxadiazole (7) reacts with nitrous acid in the presence of copper to give the nitro-compound (4), together with the deaminated compound 3-(thiazol-5-yl)-1,2,4-oxadiazole (8). Some similar deaminations have been observed.

  用三氟乙酸酐或光气和环氧丙烷将2-硝基噻唑-5-甲醛甲醛（1）脱水，得到腈（2），该腈已转化为3-（2-硝基噻唑-5-基）-1,2 ，4-恶二唑（4）。肟（1）被乙酸酐转化为2-乙酰氧基噻唑-5-腈（5），亚硫酰氯转化为2-氯噻唑-5-腈（6）。3-（2-氨基噻唑-5-基）-1,2,4-恶二唑（7）在铜存在下与亚硝酸反应生成硝基化合物（4）和脱氨基化合物3-（噻唑-5-基）-1，2，4-恶二唑（8）。已经观察到一些类似的脱氨基。
• 2-Amino-5-cyanothiazoles and their preparation
  申请人：Eastman Kodak Company

  公开号：US04324899A1

  公开（公告）日：1982-04-13

  Disclosed are novel 2-amino-5-cyanothiazoles and the preparation thereof by a novel, two-step process. The cyanothiazoles have the formula ##STR1## wherein R.sup.1 is selected from hydrogen; straight or branched alkyl of 1-20 carbons which may be substituted with 1-3 halogens; phenyl and phenyl substituted with 1-3 halogens, straight or branched alkyl of 1-20 carbons, straight or branched alkoxy of 1-20 carbons, cyano, nitro or trifluoromethyl; 2-thiophene; and .alpha.-pyridine. These compounds are useful, for example, as the diazo moiety of azo dyes prepared through diazotization and coupling with compounds such as aniline type couplers. The process for their manufacture comprises reacting in substantially anhydrous formic acid at from about 50.degree. to about 110.degree. C., hydroxylamine, preferably the salts thereof such as [NH.sub.3 OH]Cl, [NH.sub.3 OH]HSO.sub.4, [NH.sub.3 OH].sub.2 SO.sub.4, and [NH.sub.3 OH]NO.sub.3, and the corresponding 2-amino-5-formylthiazole or a salt thereof in a mole ratio of said reactants of, for example, from about 1:1 to about 2:1, and hydrolyzing the intermediate 5-cyano-2-formamidothiazole to the amine with or without prior isolation thereof.

  本发明涉及一种新型的2-氨基-5-氰基噻唑及其制备方法，该方法采用一种新的两步法。所述氰基噻唑的化学式为##STR1##其中R.sup.1选自氢；1-20个碳原子的直链或支链烷基，其可以被1-3个卤素取代；苯基和1-3个卤素取代的苯基，1-20个碳原子的直链或支链烷基，1-20个碳原子的直链或支链烷氧基，氰基，硝基或三氟甲基；2-噻吩；和α-吡啶。这些化合物可用作通过重氮化和与类苯胺偶联剂等化合物偶联制备的偶氮染料中的重氮基。其制造方法包括在基本无水的甲酸中，在大约50°C到大约110°C的温度下反应羟胺，优选其盐如[NH.sub.3 OH]Cl，[NH.sub.3 OH]HSO.sub.4，[NH.sub.3 OH].sub.2SO.sub.4和[NH.sub.3 OH]NO.sub.3，以及相应的2-氨基-5-甲酰基噻唑或其盐，其摩尔比为从大约1:1到大约2:1的反应物摩尔比，并且将中间体5-氰基-2-甲酰胺基噻唑水解为胺，可以在先前隔离或不隔离的情况下进行。
• Phenyl thiazolyl urea and carbamate derivatives as new inhibitors of bacterial cell-wall biosynthesis
  作者：Gerardo D. Francisco、Zhong Li、J.Donald Albright、Nancy H. Eudy、Alan H. Katz、Peter J. Petersen、Pornpen Labthavikul、Guy Singh、Youjun Yang、Beth A. Rasmussen、Yang-I Lin、Tarek S. Mansour

  DOI：10.1016/j.bmcl.2003.09.082

  日期：2004.1

  Over 50 phenyl thiazolyl urea and carbamate derivatives were synthesized for evaluation as new inhibitors of bacterial cell-wall biosynthesis. Many of them demonstrated good activity against MurA and MurB and gram-positive bacteria including MRSA, VRE and PRSP. 3,4-Difluorophenyl 5-cyanothiazolylurea (3p) with clog P of 2.64 demonstrated antibacterial activity against both gram-positive and gram-negative bacteria. (C) 2003 Elsevier Ltd. All rights reserved.