5-nitroso-6-phenylimidazo[2,1-b][1,3]thiazole | 16311-34-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-nitroso-6-phenylimidazo[2,1-b][1,3]thiazole
• 英文别名: 5-nitroso-6-phenylimidazo[2,1-b]thiazole；5-nitroso-6-phenyl-imidazo[2,1-b]thiazole；5-Nitroso-6-phenyl-imidazo<2,1-b>thiazol；5-Nitroso-6-phenyl-imidazo<2.1-b>thiazol；6-Phenyl-5-nitroso-imidazo<2,1-b>thiazol
• CAS: 16311-34-5
• 化学式: C₁₁H₇N₃OS
• mdl: MFCD07427163
• 分子量: 229.262
• InChiKey: RDQRJYUNUOBHRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-nitroso-6-phenylimidazo[2,1-b][1,3]thiazole 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以61%的产率得到8-Hydroxy-8-phenyl-8H-[1,2,4]oxadiazolo[3,4-c][1,4]thiazin-3-one
  参考文献：
  名称：

  Cardiovascular Characterization of [1,4]Thiazino[3,4-c][1,2,4]oxadiazol-1-one Derivatives:  Selective Myocardial Calcium Channel Modulators

  摘要：

  As an extension of previous investigations (Tetrahedron 1999, 55, 5433-5440; J. Heterocycl. Chem. 2000, 37, 875-878), a series of 21 [1,4]thiazino[3,4-c][1,2,4]oxadiazolones, which has already been synthesized (except for compounds 5a, 5b, 6), was evaluated as calcium entry blockers by functional studies, namely, in isolated guinea-pig left and right atria and K+-depolarized aortic strips. With the aim of investigating the effect of a condensed benzene ring on the molecular structure and the influence of substituents on the 8-phenyl ring of 4a, ab initio computations (RHF/3-21*G) were performed on compounds 3, 4a-d, 4f, and 4k. The results obtained show that many of the compounds studied are potent and selective negative inotropic agents; in particular, compounds 4e and 4f are about 3- and 2-fold more potent than diltiazem, respectively.

  DOI：

  10.1021/jm020815d
• 作为产物：
  描述：

  6-苯基-咪唑并[2,1-b]噻唑 在 亚硝酸特丁酯 作用下， 以 二氯甲烷 为溶剂， 以90 %的产率得到5-nitroso-6-phenylimidazo[2,1-b][1,3]thiazole
  参考文献：
  名称：

  连续流动和无外部光催化剂、氧化剂和添加剂条件下咪唑并[1,2-a]吡啶的光催化 C3–H 亚硝基化

  摘要：

  本研究报告了一种在可见光照射和连续流相结合的情况下，在没有任何外部光催化剂的情况下，在 C3 位置对咪唑并[1,2- a ]吡啶支架进行高度区域选择性光催化 C-H 亚硝基化的方案。该方案涉及温和、安全的条件，对空气和水表现出良好的耐受性，以及出色的官能团相容性和位点选择性，在光催化剂、氧化剂和添加剂的作用下以优异的产率生成各种3-亚硝基咪唑并[1,2- a ]吡啶值得注意的是，由于亚硝基化的强光吸收特性，所提出的亚硝基化反应将发色团NO引入咪唑并[1,2- a ]吡啶支架中，在可见光照射下有效发生，无需任何额外的光催化剂产品。这项研究可以指导未来开发具有广泛潜在应用的绿色有机合成策略的研究。

  DOI：

  10.1021/acs.joc.4c00173

文献信息

• Regioselective synthesis of nitrosoimidazoheterocycles using tert-butyl nitrite
  作者：Kamarul Monir、Monoranjan Ghosh、Sourav Jana、Pallab Mondal、Adinath Majee、Alakananda Hajra

  DOI：10.1039/c5ob01345c

  日期：——

  A simple and practical method has been developed for the regioselective nitrosylation of imidazopyridines via C(sp²)–H bond functionalization using tert-butyl nitrite under mild reaction conditions.

  一种简单实用的方法已经被开发出来，用于在温和的反应条件下通过C(sp²)–H键功能化使用叔丁基硝酸酯对咪唑吡啶进行区域选择性的亚硝化。
• Metal-Free Oxidative Deamination Cross-Coupling of Imidazo­heterocycles with 2-Aminobenzothiazoles
  作者：Ri-Yuan Tang、Xiao-Ming Ji、Li Xu、Yun Yan、Fan Chen

  DOI：10.1055/s-0035-1560395

  日期：——

  metal-free oxidative deamination–cross-coupling of imidazoheterocycles with 2-aminobenzothiazoles in the presence of tert-butyl nitrite is reported for the first time. This simple protocol tolerates a wide range of functional groups to afford various benzothiazole–imidazoheterocycles in moderate to excellent yields, with the release of nitrogen and water as benign byproducts. A metal-free oxidative deam

  摘要 首次报道了在亚硝酸叔丁酯存在下，咪唑杂环与2-氨基苯并噻唑的无金属氧化脱氨交联反应。这个简单的方案可耐受各种官能团，以中等至极好的收率提供各种苯并噻唑-咪唑杂环，并释放出氮和水作为良性副产物。 首次报道了在亚硝酸叔丁酯存在下，咪唑杂环与2-氨基苯并噻唑的无金属氧化脱氨交联反应。这个简单的方案可耐受各种官能团，以中等至极好的收率提供各种苯并噻唑-咪唑杂环，并释放出氮和水作为良性副产物。
• Novel pyrido-imidazo-indoles, compositions and method therewith
  申请人：——

  公开号：US04143142A1

  公开（公告）日：1979-03-06

  Compounds of the formula: ##STR1## AND PHARMACEUTICALLY ACCEPTABLE ACID ADDITION SALTS THEREOF WHEREIN R, R.sub.1, R.sub.2, R.sub.3, are selected from the group consisting of hydrogen, halogen and lower-alkyl of from one to four carbon atoms, inclusive; with the proviso that taken together they constitute the following substituents on the tetracyclic ring, 10-halo, 8,10-dihalo, 8,9-di-lower-alkyl, and 7,9-dilower-alkyl; R', R'.sub.1, R'.sub.2, and R'.sub.3 are selected from the group consisting of hydrogen, halogen and lower alkyl of from one to four carbon atoms, inclusive, with the proviso that when taken together they constitute the following substituents, 1-halo, 2-halo, 3-halo, 4-halo, 1-lower-alkyl, 2-lower-alkyl, 3-lower-alkyl, 4-lower-alkyl, 1,3-dihalo, 2,3-dihalo, 2,4-dihalo, 3,4-dihalo, 1,3-di-lower-alkyl, 2,3-di-lower-alkyl, 1,4-di-lower-alkyl; R.sub.4, R.sub.5, R.sub.6, and R.sub.7 are selected from the group consisting of hydrogen, halogen and lower-alkyl of from one to four carbon atoms, inclusive, with the proviso that when taken together they constitute the following substituents on the tetracyclic ring, 9-halo, 8-halo, 7-halo, 6-halo, 9-lower-alkyl, 8-lower-alkyl, 7-lower-alkyl, 6-lower-alkyl, 7,9-dihalo, 7,8-dihalo, 6,8-dihalo, 6,7-dihalo, 7,9-di-lower-alkyl, 7,9-di-lower-alkyl, 7,8-di-lower-alkyl, and 4,6-di-lower-alkyl. R.sub.8 is selected from the group consisting of hydrogen, lower-alkyl of from one to four carbon atoms, inclusive, and R.sub.9 is selected from the group consisting of hydrogen and halo. These compounds are useful as anti-hypertensive agents in mammals. This is a division of application Ser. No. 726,390, filed Sept. 24, 1976, now abandoned.

  该公式化合物为：## STR1 ## 及其药用可接受的酸盐，其中R，R.sub.1，R.sub.2，R.sub.3选择自氢，卤素和碳数为1至4的低碳基，包括; 前提是它们一起构成四环环上的以下取代基，10卤素，8,10二卤素，8,9-二低碳基和7,9-二低碳基; R'，R'.sub.1，R'.sub.2和R'.sub.3选择自氢，卤素和碳数为1至4的低碳基，包括，前提是当它们一起构成以下取代基时，1卤素，2卤素，3卤素，4卤素，1-低碳基，2-低碳基，3-低碳基，4-低碳基，1,3-二卤素，2,3-二卤素，2,4-二卤素，3,4-二卤素，1,3-二低碳基，2,3-二低碳基，1,4-二低碳基; R.sub.4，R.sub.5，R.sub.6和R.sub.7选择自氢，卤素和碳数为1至4的低碳基，包括，前提是当它们一起构成四环环上的以下取代基时，9卤素，8卤素，7卤素，6卤素，9-低碳基，8-低碳基，7-低碳基，6-低碳基，7,9-二卤素，7,8-二卤素，6,8-二卤素，6,7-二卤素，7,9-二低碳基，7,9-二低碳基，7,8-二低碳基和4,6-二低碳基。R.sub.8选择自氢，碳数为1至4的低碳基，包括，R.sub.9选择自氢和卤素。这些化合物在哺乳动物中作为抗高血压剂有用。这是申请号为726,390，于1976年9月24日提交的申请的分案，现已废弃。
• Derivatives of imidazo[2,1-b] thiazole
  申请人：——

  公开号：US04204067A1

  公开（公告）日：1980-05-20

  Compounds of the formula: ##STR1## and pharmaceutically acceptable acid addition salts thereof wherein R, R.sub.1, R.sub.2, R.sub.3, are selected from the group consisting of hydrogen, halogen and lower-alkyl of from one to four carbon atoms, inclusive; with the proviso that taken together they constitute the following substituents on the tetracydic ring, 10-halo, 8,10-dihalo, 8,9-di-lower-alkyl, and 7,9-dilower-alkyl; R', R'.sub.1, R'.sub.2, and R'.sub.3 are selected from the group consisting of hydrogen, halogen and lower alkyl of from one to four carbon atoms, inclusive, with the proviso that when taken together they constitute the following substituents, 1-halo, 2-halo, 3-halo, 4-halo, 1-lower-alkyl, 2-lower-alkyl, 3-lower-alkyl, 4-lower-alkyl, 1,3-dihalo, 2,3-dihalo, 2,4-dihalo, 3,4-dihalo, 1,3-di-lower-alkyl, 2,3-di-lower-alkyl, 1,4-di-lower-alkyl; R.sub.4, R.sub.5, R.sub.6, and R.sub.7 are selected from the group consisting of hydrogen, halogen and lower-alkyl of from one to four carbon atoms, inclusive, with the proviso that when taken together they constitute the following substituents on the tetracyclic ring, 9-halo, 8-halo, 7-halo, 6-halo, 9-lower-alkyl, 8-lower-alkyl, 7-lower-alkyl, 6-lower-alkyl, 7,9-dihalo, 7,8-dihalo, 6,8,-dihalo, 6,7-dihalo, 79-di-lower-alkyl, 7,9-di-lower-alkyl, 7,8-di-lower-alkyl, and 4,6-di-lower-alkyl. R.sub.8 is selected from the group consisting of hydrogen, lower-alkyl of from one to four carbon atoms, inclusive, and R.sub.9 is selected from the group consisting of hydrogen and halo. These compounds are useful as anti-hypertensive agents in mammals.

  化合物的式子为：##STR1##以及其药学上可接受的酸盐，其中R、R.sub.1、R.sub.2、R.sub.3从氢、卤素和含1至4个碳原子的低碳基中选择；但要注意它们在四环状环上的取代基是10-卤代、8,10-双卤代、8,9-二-低碳基和7,9-二-低碳基；R'、R'.sub.1、R'.sub.2和R'.sub.3从氢、卤素和含1至4个碳原子的低碳基中选择，但要注意当它们一起组成以下取代基时，即1-卤代、2-卤代、3-卤代、4-卤代、1-低碳基、2-低碳基、3-低碳基、4-低碳基、1,3-双卤代、2,3-双卤代、2,4-双卤代、3,4-双卤代、1,3-二-低碳基、2,3-二-低碳基、1,4-二-低碳基；R.sub.4、R.sub.5、R.sub.6和R.sub.7从氢、卤素和含1至4个碳原子的低碳基中选择，但要注意当它们一起组成以下取代基时，即9-卤代、8-卤代、7-卤代、6-卤代、9-低碳基、8-低碳基、7-低碳基、6-低碳基、7,9-双卤代、7,8-双卤代、6,8,-双卤代、6,7-双卤代、79-二-低碳基、7,9-二-低碳基、7,8-二-低碳基和4,6-二-低碳基。R.sub.8从氢和含1至4个碳原子的低碳基中选择，而R.sub.9从氢和卤素中选择。这些化合物在哺乳动物中可用作降压剂。
• Pyl,T. et al., Justus Liebigs Annalen der Chemie, 1962, vol. 657, p. 113 - 120
  作者：Pyl,T. et al.

  DOI：——

  日期：——