3,10-dihydro-2H-imidazo[2,1-b]quinazolin-5-one | 32725-30-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3,10-dihydro-2H-imidazo[2,1-b]quinazolin-5-one
• 英文别名: 2,3-dihydro-3H-imidazo[2,1-b]quinazolin-1(10)H-5-one；2,3-dihydroimidazo[2,1-b]quinazolin-10H-5-one；2,3-dihydro-1(10)H-imidazo[2,1-b]quinazolin-5-one
• CAS: 32725-30-7
• 化学式: C₁₀H₉N₃O
• mdl: MFCD00838601
• 分子量: 187.2
• InChiKey: HSHIBZRPJZBQRU-UHFFFAOYSA-N

物化性质

• 熔点：
  262-264 °C(Solv: methanol (67-56-1))
• 沸点：
  350.9±25.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  44.7
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,10-dihydro-2H-imidazo[2,1-b]quinazolin-5-one 在 phosphorous (V) sulfide 作用下， 以 吡啶 为溶剂， 以84%的产率得到2,3-Dihydro-5H,10H-imidazo<2,1-b>chinazolin-5-thion
  参考文献：
  名称：

  Leistner, Siegfried; Wagner, Guenther; Hentschel, Karin, Zeitschrift fur Chemie, 1980, vol. 20, # 4, p. 143 - 144

  摘要：

  DOI：

文献信息

• Divergent 2‐Chloroquinazolin‐4(3 <i>H</i> )‐one Rearrangement: Twisted‐Cyclic Guanidine Formation or Ring‐Fused <i>N</i> ‐Acylguanidines via a Domino Process
  作者：Gang Yan、Bereket L. Zekarias、Xiaoyu Li、Victor A. Jaffett、Ilia A. Guzei、Jennifer E. Golden

  DOI：10.1002/chem.201905219

  日期：2020.2.21

  rearrangement/intramolecular cyclization, gated through (E)‐twisted‐cyclic guanidines, to afford ring‐fused N‐acylguanidines. This scalable, structurally tolerant transformation generated 55 guanidines and delivered twisted‐cyclic guanidines with robust plasma stability and an abbreviated total synthesis of an antitumor ring‐fused guanidine (4 steps, 55 % yield).

  开发了一种高效的 2-氯喹唑啉-4(3 H )-酮重排，可预测地在一次操作中产生扭曲的环状或稠合的胍，这取决于伴随的二胺试剂中伯胺与仲胺的存在。2-氯喹唑啉酮与仲二胺的配对导致扭曲环状胍的独特形成。使用含伯胺的二胺允许多米诺喹唑啉酮重排/分子内环化，通过 ( E )-扭曲的环状胍进行门控，得到环稠合的N‐酰基胍。这种可扩展的、结构耐受的转化产生了 55 种胍，并提供了具有强大血浆稳定性的扭曲环状胍和一种抗肿瘤环稠合胍的简化全合成（4 步，55% 收率）。
• Synthesis of 2,4-Diaminoquinazolines and Tricyclic Quinazolines by Cascade Reductive Cyclization of Methyl <i>N</i>-Cyano-2-nitrobenzimidates
  作者：Ping Yin、Nan Liu、Yu-Xing Deng、Yue Chen、Yong Deng、Ling He

  DOI：10.1021/jo2023697

  日期：2012.3.16

  An efficient route to N4-substituted 2,4-diaminoquinazolines has been developed by employing tandem condensation of cyanoimidate–amine and reductive cyclization in iron–HCl system. This method is tolerant of a following intramolecular N-alkylation and produces two fused heterocycles in a one-pot procedure. This protocol is a facile two-step synthesis of tricyclic quinazolines, which is effected by

  通过使用氰基亚氨酸酯-胺的串联缩合和铁-HCl体系中的还原环化，已开发出一种高效的N 4取代的2,4-二氨基喹唑啉路线。该方法耐受随后的分子内N-烷基化，并在一锅法中产生两个稠合的杂环。该协议是三环喹唑啉的两步合成方法，该方法可通过有效的氰基亚酰胺化作用和2-硝基苯甲醛的串联还原环化作用来实现。此外，已经从开环/闭环级联的角度研究了三环喹唑啉的形成过程。发现以高收率制备三环喹唑啉酮依赖于碱或酸体系中三环喹唑啉的选择性水解。
• Mechanism of the reaction of neutral and anionic N-nucleophiles with α-halocarbonyl compounds
  作者：A. S. Morkovnik、L. N. Divaeva、V. A. Anisimova

  DOI：10.1007/s11172-007-0182-1

  日期：2007.6

  N-Acylalkylation of neutral and anionic N-nucleophiles with α-halocarbonyl compounds was investigated by quantum chemical methods in terms of the density functional theory and by experimental methods for 2,3-dihydroimidazo[2,1-b]quinazolin-1(10)H-5-one, its N-anion, and simpler model structures. High reactivity of these reagents is determined primarily by stabilization of transition states (TS) by bridge bonds involving halogen or nitrogen atoms rather than by conjugation, as has been commonly accepted. Bridged TS are formed by both the substitution mechanism S N 2 and the addition-elimination mechanism. α-Haloalkyl-substituted zwitterions, which are potential intermediates of stepwise N-acylalkylation of neutral N-nucleophiles, do not exist in the isolated state, but they are rather efficiently stabilized upon solvation. These zwitterions, as well as analogous O-anions generated from anionic N-nucleophiles, can serve as intermediates of N-acylalkylation, as was demonstrated by localization of the corresponding TS.

  通过量子化学方法研究了中性和阴离子 N-核亲和剂与 α-卤代羰基化合物的 N-酰烷基化反应，包括密度泛函理论以及 2,3-二氢咪唑并[2,1-b]喹唑啉-1(10)H-5-酮、其 N-阴离子和更简单的模型结构的实验方法。这些试剂的高反应活性主要是由涉及卤素原子或氮原子的桥键对过渡态（TS）的稳定作用决定的，而不是像人们通常认为的那样是由共轭作用决定的。桥键过渡态可通过取代机理 S N 2 和加成-消除机理形成。α-卤代烷基取代型三聚氰胺是中性 N-亲核物逐步 N-酰烷基化的潜在中间体，它们在孤立状态下并不存在，但在溶解后会有效地稳定下来。这些齐聚物以及由阴离子 N-亲核物生成的类似 O-阴离子可以作为 N-酰基烷基化的中间体，相应 TS 的定位也证明了这一点。
• A rapid and convenient synthesis of novel 1-imino-2,3-dihydro-1H-pyrazino[2,1,-b]quinazolin-5-ones
  作者：Maria de Fatima Pereira、François René Alexandre、Valérie Thiéry、Thierry Besson

  DOI：10.1016/j.tetlet.2004.02.095

  日期：2004.4

  Exploring original approaches for the synthesis of therapeutic agents having a quinazoline part, we discovered that novel 3,4-dihydro-2H-pyrazino[2,1,-b]quinazolines (3) may be rapidly and easily obtained via the chemistry of 4,5-dichloro-1,2,3-dithiazolium chloride (1). Our synthetic approach of this reaction is described with the aim of obtaining a well-controlled access to this very rarely described

  探索合成具有喹唑啉部分的治疗剂的原始方法，我们发现可以通过化学反应快速，轻松地获得新型3,4-二氢-2 H-吡嗪并[2,1，-b ]喹唑啉（3）。 4,5-二氯-1,2,3-二噻唑鎓盐（1）。描述了我们对该反应的合成方法，其目的是获得对这种很少描述的吡嗪并[2,1，-b ]喹唑啉骨架的良好控制通道。
• Synthesis of novel 2,3-substituted quinazolin-4-ones by condensation of alkyl or aromatic diamines with 5-(N-arylimino)-4-chloro-5H-1,2,3-dithiazoles
  作者：Maria de Fatima Pereira、Valérie Thiéry、Thierry Besson

  DOI：10.1016/j.tet.2006.11.028

  日期：2007.1

  N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-anthranilates to afford quinazolines, which are very interesting starting materials for the access to novel 2,3-condensed quinazolin-4-ones. On the other side, aromatic amines allow the synthesis of polycyclic molecules, which are structurally close to the model natural products (e.g., rutaecarpine, luotonine, tryptanthrine and vasicinone).

  本文描述的工作是Appel盐在新型杂环概念中的效用的另一个示例。我们证实，伯烷基二胺可能容易与N-（4-氯-5 H -1,2,3-二噻唑-5-亚甲基）-邻氨基苯甲酸甲酯反应生成喹唑啉，这是获得新颖化合物的非常有趣的起始原料2,3-缩合的喹唑啉-4-酮。另一方面，芳族胺允许合成多环分子，该多环分子在结构上接近模型天然产物（例如，芸香芸香碱，色氨酸，色氨酸和血管紧张素）。