2-bromobenzo[4,5]imidazo[2,1-b]quinazolin-12(6H)-one | 923951-12-6

• 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: 2-bromobenzo[4,5]imidazo[2,1-b]quinazolin-12(6H)-one
• 英文别名: 2-bromobenz[4,5]imidazo[2,1-b]quinazolin-12(6H)-one；2-bromobenzimidazo[2,1-b]quinazoline-12(6H)-one；2-bromobenzimidazo[2,1-b]quinazolin-12(6H)one；2-bromo-6H-benzimidazolo[2,1-b]quinazolin-12-one
• CAS: 923951-12-6
• 化学式: C₁₄H₈BrN₃O
• 分子量: 314.141
• InChiKey: UKNGUFYNGKRBSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  2-bromobenzo[4,5]imidazo[2,1-b]quinazolin-12(6H)-one 、 2-(氯羰基)苯甲酸甲酯 生成 6-(2-Carbomethoxybenzoyl)-2-bromobenzimidazo[2,1-b]quinazolin-12(6H)one
  参考文献：
  名称：

  Immunosuppressants

  摘要：

  苯并咪唑[2,1-b]喹唑啉-12(6H)酮，是一种免疫抑制剂和治疗自身免疫性疾病的药物，可通过以下方法制备：(1)将2-氯苯并咪唑与蒽酰氨或酯反应；(2)在三氟乙酸存在下，将2-氨基苯并咪唑与蒽酰氨或酯反应；(3)将2-甲基硫代苯并咪唑与蒽酰卤化物水合物反应。

  公开号：

  US04000275A1
• 作为产物：
  描述：

  在 barium hydroxide octahydrate 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.43h， 以435 mg的产率得到2-bromobenzo[4,5]imidazo[2,1-b]quinazolin-12(6H)-one
  参考文献：
  名称：

  Microwave-Mediated Heterocyclization to Benzimidazo[2,1-b]quinazolin-12(5H)-ones

  摘要：

  An effective route to benzimidazo[2,1-b]quinazolin-12(5H)-ones from commercially available o-aryl isothiocyanate esters and o-phenylenediamines is reported. This method accommodates a variety of substituents on either starting material and proceeds under microwave irradiation in the presence of barium hydroxide, conditions that do not hydrolyze methyl ester substituents. The pharmacologically pertinent benzimidazoquinazolinone heterocycle is delivered in excellent yield and purity via both solution- and solid-phase protocols, the latter involving traceless release from the resin.

  DOI：

  10.1021/jo0618066

文献信息

• Copper-Catalyzed Domino Synthesis of Benzimidazo[2,1-b]quin- azolin-12(6H)-ones Using Cyanamide as a Building Block
  作者：Daoshan Yang、Yuyuan Wang、Haijun Yang、Tao Liu、Hua Fu

  DOI：10.1002/adsc.201100580

  日期：2012.2

  A convenient copper-catalyzed domino method for the synthesis of benzimidazo[2,1-b]quinazolin-12(6H)-ones has been developed via reactions of readily available substituted 2-bromo-N-(2-halophenyl)benzamides with cyanamide, in which cyanamide acts as a useful building block.

  通过容易获得的取代的2-溴-N-（2-卤代苯基）苯甲酰胺与苯的反应，开发了一种方便的铜催化多米诺骨牌合成苯并咪唑并[2,1 - b ]喹唑啉-12（6 H）-酮的方法。氰酰胺，其中氰酰胺可作为有用的结构单元。
• Divergent Approach for Regioselective Synthesis of Linearly and Angularly Fused Benzoimidazoquinazolinones from Isatoic Anhydrides
  作者：Mookda Pattarawarapan、Dolnapa Yamano、Surat Hongsibsong、Wong Phakhodee

  DOI：10.1021/acs.joc.2c02317

  日期：2022.12.2

  regioselective syntheses of a wide range of linearly and angularly fused benzoimidazoquinazolinones. The selectivity of the products relies on the generation of either highly electrophilic oxyphosphonium or less reactive imidate intermediates. A direct amine attack at the C-2 position of the oxyphosphonium intermediate presumably drives the reaction toward the linearly fused products, whereas an attack of

  Ph 3 P–I 2介导的靛红酸酐和邻苯二胺的缩合反应已被开发用于区域选择性合成各种线性和角稠合的苯并咪唑并喹唑啉酮。产品的选择性取决于高度亲电性氧磷或反应性较低的亚胺酸酯中间体的产生。胺直接攻击氧膦中间体的 C-2 位可能会推动反应向线性稠合产物的方向发展，而二胺在原位生成的环状亚胺酸酯的 C-4 位的攻击会导致有角稠合的衍生物。该策略可作为有效合成其他相关杂环的实用方法。
• N-(2-Carboxyphenyl)oxalamides in the synthesis of the quinazoline central nervous system depressant methaqualone and fused biheterocyclic systems
  作者：V. L. Mamedova、T. A. Kushatov、N. A. Tikhomirova、O. G. Sinyashin、V. A. Mamedov

  DOI：10.1007/s11172-024-4319-2

  日期：2024.7

  A synthesis of the quinazolin-4-one pharmacological agent methaqualone from N-(2-carboxyphenyl)oxalamide was developed. A new method for the reductive cyclization of 3-(2-nitrophenyl)quinazolin-4-ones to benzimidazo[2,1-b]quinazolin-12(6H)-ones, the 6-deoxo-6-aza analogs of natural alkaloid tryptanthrine, was suggested and new derivatives of poorly available quinoxalinoquinazolinone fused system were

  开发了以N- (2-羧基苯基)草酰胺为原料合成喹唑啉-4-酮药物甲喹酮的方法。 3-(2-硝基苯基)喹唑啉-4-酮还原环化为天然产物6-脱氧-6-氮杂类似物苯并咪唑[2,1 -b ]喹唑啉-12(6 H )-酮的新方法提出了生物碱色胺酮，并合成了难以利用的喹喔啉喹唑啉酮稠合系统的新衍生物。
• MATERIALS FOR ELECTRONIC DEVICES
  申请人：Stoessel Philipp

  公开号：US20130092922A1

  公开（公告）日：2013-04-18

  The present invention relates to an electronic device comprising anode, cathode and at least one organic layer which comprises a compound of the formula (I) to (IV). The invention furthermore encompasses the use of compounds of the formula (I) to (IV) in an electronic device and to a compound of the formula (Ic) to (IVc).
• US4000275A
  申请人：——

  公开号：US4000275A

  公开（公告）日：1976-12-28