2-amino-1-imino-9,10-dimethoxy-13-phenyl-2,6,7,13-tetrahydro-1H-pyrimido[5',4':5,6]pyrido-[2,1-a]isoquinoline-12-carbonitrile | 1137166-82-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶并嘧啶类
• 英文名称: 2-amino-1-imino-9,10-dimethoxy-13-phenyl-2,6,7,13-tetrahydro-1H-pyrimido[5',4':5,6]pyrido-[2,1-a]isoquinoline-12-carbonitrile
• 英文别名: 5-Amino-6-imino-13,14-dimethoxy-8-phenyl-1,3,5-triazatetracyclo[8.8.0.02,7.011,16]octadeca-2(7),3,9,11,13,15-hexaene-9-carbonitrile；5-amino-6-imino-13,14-dimethoxy-8-phenyl-1,3,5-triazatetracyclo[8.8.0.02,7.011,16]octadeca-2(7),3,9,11,13,15-hexaene-9-carbonitrile
• CAS: 1137166-82-5
• 化学式: C₂₄H₂₂N₆O₂
• 分子量: 426.478
• InChiKey: SBGWBRDFSDZTQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-amino-1-imino-9,10-dimethoxy-13-phenyl-2,6,7,13-tetrahydro-1H-pyrimido[5',4':5,6]pyrido-[2,1-a]isoquinoline-12-carbonitrile 在 一水合肼 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 9,10-dimethoxy-1-(2-(4-methoxybenzylidene)hydrazinyl)-13-phenyl-7,13-dihydro-6H-pyrimido[5',4':5,6]pyrido[2,1-a]isoquinoline-12-carbonitrile
  参考文献：
  名称：

  吡啶并[2,1-a]异喹啉-4-基甲亚氨酸酯衍生物的合成与反应及分离产物的抗菌活性

  摘要：

  亚芳丙二腈的治疗2A - c ^与1- cyanomethylisoquinoline 1，得到4-氨基-2- arylpyrido [2,1-一个]异喹啉-1,3-二腈衍生物5A - Ç，其转化为formimidates 6A - Ç 经由反应与原甲酸三乙酯。用水合肼处理后一化合物，得到相应的氨基亚氨基化合物7A – C，将其进行Dimroth重排，得到13-芳基-1-肼基嘧啶基[5'，4'：5,6]吡啶基[2,1- a ] ]异喹啉-12-腈8A – C。后者与醛反应生成9a - i。后一种化合物9a - i的氧化环化反应得到[1,2,4] triazolo [4“，3”：1'，6']-嘧啶[5'，4'：5,6] pyrido [2,1- a ]异喹啉10a，d，g。此类化合物异构化为热力学上更稳定的异构体[1,2,4]三唑[1“，5”：1'，6']嘧啶[5'，4'：5,6]-吡啶[2

  DOI：

  10.1002/jhet.2891
• 作为产物：
  描述：

  ethyl N-(1,3-dicyano-9,10-dimethoxy-2-phenyl-6,7-dihydro-2H-benzo[a]quinolizin-4-yl)methanimidate 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以63%的产率得到2-amino-1-imino-9,10-dimethoxy-13-phenyl-2,6,7,13-tetrahydro-1H-pyrimido[5',4':5,6]pyrido-[2,1-a]isoquinoline-12-carbonitrile
  参考文献：
  名称：

  Synthesis of Tetra- and Pentaheterocyclic Compounds Incorporated Isoquinoline Moiety

  摘要：

  7-Amino-2,3-dimethoxy-9-phenyl-5,6,9,6a-tetrahydropyridino[2,1-a]isoquinoline-8,10-dicarbonitrile 5 was prepared via Michael addition reaction of benzylidenemalononitrile 2 with isoquinoline-1-carbonitrile 1. Reaction of 5 with triethyl orthoformate and formamide led to the formation of the corresponding 4-ethoxymethylene and 4-aminopyrimidine derivatives of benzo[a]quinolizines 6 and 7, respectively. Compound 6 reacted with hydrazine to give imino-amino compound 8. The latter compound reacted with formic acid, triethyl orthoformate, acetic anhydride or benzoyl chloride to give the triazolopyrimidine derivatives 9, 10 and 11, respectively. Compound 8 reacted with hydrazonoyl halides 12, 13 and diethyl oxalate to give triazinopyrimidine and triazolopyrimidine derivatives 16, 17 and 20, respectively.

  DOI：

  10.3987/com-08-11481

文献信息

• Synthesis of Tetra- and Pentaheterocyclic Compounds Incorporated Isoquinoline Moiety
  作者：Tayseer A. Abdallah、Hamdi M. Hassaneen、Hyam A. Abdelhadi

  DOI：10.3987/com-08-11481

  日期：——

  7-Amino-2,3-dimethoxy-9-phenyl-5,6,9,6a-tetrahydropyridino[2,1-a]isoquinoline-8,10-dicarbonitrile 5 was prepared via Michael addition reaction of benzylidenemalononitrile 2 with isoquinoline-1-carbonitrile 1. Reaction of 5 with triethyl orthoformate and formamide led to the formation of the corresponding 4-ethoxymethylene and 4-aminopyrimidine derivatives of benzo[a]quinolizines 6 and 7, respectively. Compound 6 reacted with hydrazine to give imino-amino compound 8. The latter compound reacted with formic acid, triethyl orthoformate, acetic anhydride or benzoyl chloride to give the triazolopyrimidine derivatives 9, 10 and 11, respectively. Compound 8 reacted with hydrazonoyl halides 12, 13 and diethyl oxalate to give triazinopyrimidine and triazolopyrimidine derivatives 16, 17 and 20, respectively.
• Synthesis and Reactions of Pyrido[2,1-<i>a</i>]isoquinolin-4-yl Formimidate Derivatives and Antimicrobial Activities of Isolated Products
  作者：Hamdi M. Hassaneen、Wagnat W. Wardakhan、Yasmin Sh. Mohammed

  DOI：10.1002/jhet.2891

  日期：2017.9

  4‐amino‐2‐arylpyrido[2,1‐a]isoquinoline‐1,3‐dicarbonitrile derivatives 5A–C, which converted to formimidates 6A–C via reaction with triethylorthoformate. Treatment of the latter compounds with hydrazine hydrate gave the corresponding amino–imino compounds 7A–C, which underwent Dimroth rearrangement to afford 13‐aryl‐1‐hydrazinylpyrimido[5′,4′:5,6]pyrido[2,1‐a]isoquinoline‐12‐carbonitrile 8A–C. The latter

  亚芳丙二腈的治疗2A - c ^与1- cyanomethylisoquinoline 1，得到4-氨基-2- arylpyrido [2,1-一个]异喹啉-1,3-二腈衍生物5A - Ç，其转化为formimidates 6A - Ç 经由反应与原甲酸三乙酯。用水合肼处理后一化合物，得到相应的氨基亚氨基化合物7A – C，将其进行Dimroth重排，得到13-芳基-1-肼基嘧啶基[5'，4'：5,6]吡啶基[2,1- a ] ]异喹啉-12-腈8A – C。后者与醛反应生成9a - i。后一种化合物9a - i的氧化环化反应得到[1,2,4] triazolo [4“，3”：1'，6']-嘧啶[5'，4'：5,6] pyrido [2,1- a ]异喹啉10a，d，g。此类化合物异构化为热力学上更稳定的异构体[1,2,4]三唑[1“，5”：1'，6']嘧啶[5'，4'：5,6]-吡啶[2