1,3,8,8-tetramethyl-6,7-dihydropyrimido<4,5-b>quinoline-2,4,6(1H,3H,7H)-trione

• 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: 1,3,8,8-tetramethyl-6,7-dihydropyrimido<4,5-b>quinoline-2,4,6(1H,3H,7H)-trione
• 英文别名: 1,3,8,8-tetramethyl-1,2,3,4,6,7,8,9-octahydropyrimidino[4,5-b]quinoline-2,4,6-trione；1,3,8,8-tetramethyl-8,9-dihydropyrimido[4,5-b]quinoline-2,4,6(1H,3H,7H)-trione；1,3,8,8-tetramethyl-7,9-dihydropyrimido[4,5-b]quinoline-2,4,6-trione
• 化学式: C₁₅H₁₇N₃O₃
• 分子量: 287.318
• InChiKey: JPZQHEGWVRKLSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  70.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (5-(4-(dimethylamino)phenyl)-1,3,8,8-tetramethyl-7,8,9,10-tetrahydropyrimido[4,5-b]quinoline-2,4,6(1H,3H,5H)-trione) 在 溶剂黄146 作用下， 反应 2.0h， 以95%的产率得到1,3,8,8-tetramethyl-6,7-dihydropyrimido<4,5-b>quinoline-2,4,6(1H,3H,7H)-trione
  参考文献：
  名称：

  芳基化脱芳基对4-（二甲基氨基）苯甲醛，环己烷-1,3-二酮和一些1,3- [N，C]二亲核试剂的汉茨环缩合反应

  摘要：

  4-（二甲基氨基）苯甲醛，环己烷-1,3-二酮和一些1,3- [N，C]-二亲核试剂（5-氨基-3-甲基-1-苯基吡唑，3， 5-二甲氧基苯胺和4-氨基-1,3-二甲基嘧啶-2,6-二酮）在沸腾的乙酸中进行分解，分离出N，N-二甲基苯胺，并形成带有γ-未取代的吡啶环的缩合杂环系统（吡唑并[3,4- b ]喹啉，a啶和嘧啶并[4,5- b ]喹啉）。

  DOI：

  10.1007/s10593-009-0250-6

文献信息

• An Efficient synthesis of pyrimido[4,5-<i>b</i>]quinoline and indeno[2′,1′:5,6]pyrido[2,3-<i>d</i>]pyrimidine derivatives via multicomponent reactions in ionic liquid
  作者：Shun-Jun Ji、Sai-Nan Ni、Fang Yang、Jing-Wen Shi、Guo-Lan Dou、Xiao-Yue Li、Xiang-Shan Wang、Da-Qing Shi

  DOI：10.1002/jhet.5570450310

  日期：2008.5

  A series of pyrimido[4,5-b]quinoline and indeno[2′,1′:5,6]pyrido[2,3-d]pyrimidine derivatives were synthesized via the three-component reaction of an aldehyde, 6-aminopyrimidine-2,4-dione and 5,5-dimethyl-1,3-cyclohexanedione or 1,3-indanedione in ionic liquid 1-n-butyl-3-methylimidazolium bromide ([bmim]Br). This protocol has the advantages of easier work-up, milder reaction conditions, high yields

  通过醛6-氨基嘧啶的三组分反应合成了一系列嘧啶并[4,5- b ]喹啉和茚并[2'，1'：5,6]吡啶[2,3- d ]嘧啶衍生物离子液体1 - n-丁基-3-甲基咪唑鎓溴化物（[bmim] Br）中的-2,4-二酮和5,5-二甲基-1,3-环己二酮或1,3-茚满二酮。与其他方法相比，该方案的优点是后处理容易，反应条件温和，收率高且对环境无害。
• Synthesis, characterization, DFT, QSAR, antimicrobial, and antitumor studies of some novel pyridopyrimidines
  作者：Zeinab Hussain、Magdy A. Ibrahim、Nasser M. El-Gohary、Al-Shimaa Badran

  DOI：10.1016/j.molstruc.2022.133870

  日期：2022.12

  compounds revealed good to excellent activities against colon carcinoma cell lines (HCT-116) and human Hepatocellular carcinoma cell lines (HePG-2). Compounds 5 and 10-12 showed higher antiproliferative activity (from 2.68 to 16.82 µg/mL) against the two types of cancer cell lines as compared with the reference drug (5-fluoeouracil). Quantitative structure activity relationship (QSAR models) were created

  6-Amino-5-formyluracil ( 1 ) 被有效地用于构建多种新型异环嘧啶。化合物1与一些环状活性亚甲基酮（包括 1,3-环己二酮、二甲酮、1,3-茚满二酮、取代的吡唑啉酮、1,3-噻唑烷-2,4-二酮和硫代巴比妥酸）的Friedländer 缩合反应得到多种稠合杂环吡啶并[2,3-d]嘧啶。化合物1与5-氨基-3-甲基-1 H-吡唑、6-氨基尿嘧啶和6-氨基-1,3-二甲基尿嘧啶等环状烯胺反应生成吡唑并[4',3':5,6]吡啶并[ 2,3-d]嘧啶和嘧啶并[5',4':5,6]吡啶并[2,3-d]嘧啶。此外，化合物1的反应与一些杂环烯醇即 4-hydroxycoumarin、1-ethyl-4-hydroxyquinolin-2(1 H )-one 和 2-hydroxy-4 H -pyrido[1,2-a]pyrimidin-4-one 产生多种 polyfused系统。在
• Acid catalysed enamine induced transformations of 1,3-dimethyl-5-formyluracil. A unique annulation reaction with enaminones
  作者：Harjit Singh Dolly、Swapandeep Singh Chimni、Subodh Kumar

  DOI：10.1016/0040-4020(95)00831-r

  日期：1995.11

  1,3-Dimethyl-5-formyluracil (1) with enaminones, 3-amino-5,5-dimethylcyclohex-2-enone and 3-aminocyclohex-2-enone in CH3CN - TFA (10 : 0.1) gives annulation products pyrimido[4,5-b]quinolin-2,4,6(1H, 3H, 7H)-trione derivatives along with Hantzsch type 1,4-dihydropyridine derivatives. However, 1 with ethyl beta-aminocrotonate and 6-amino-1.3-dimethyluracil, enamine ester and amide respectively, provides subsequent transformation products.
• El-Ahl, Abdel Aziz S.; El Bialy, Serry A.A.; Ismail, Mohamed A., Heterocycles, 2001, vol. 55, # 7, p. 1315 - 1321
  作者：El-Ahl, Abdel Aziz S.、El Bialy, Serry A.A.、Ismail, Mohamed A.

  DOI：——

  日期：——
• Aromatization with dearylation on Hantzsch cyclocondensation of 4-(dimethylamino)benzaldehyde, cyclohexane-1,3-diones, and some 1,3-[N,C]dinucleophiles
  作者：I. B. Dzvinchuk、N. A. Tolmachova、A. N. Chernega、M. O. Lozinskii

  DOI：10.1007/s10593-009-0250-6

  日期：2009.2

  three-component cyclization of 4-(dimethylamino)benzaldehyde, cyclohexane-1,3-diones, and some 1,3-[N,C]-dinucleophiles (5-amino-3-methyl-1-phenylpyrazole, 3,5-dimethoxyaniline, and 4-amino-1,3-dimethylpyrimidine-2,6-dione) proceeds in boiling acetic acid with the splitting off N,N-dimethylaniline and the formation of polycondensed heterocyclic sytems with a γ-unsubstituted pyridine ring (pyrazolo[3,4-b]quinoline

  4-（二甲基氨基）苯甲醛，环己烷-1,3-二酮和一些1,3- [N，C]-二亲核试剂（5-氨基-3-甲基-1-苯基吡唑，3， 5-二甲氧基苯胺和4-氨基-1,3-二甲基嘧啶-2,6-二酮）在沸腾的乙酸中进行分解，分离出N，N-二甲基苯胺，并形成带有γ-未取代的吡啶环的缩合杂环系统（吡唑并[3,4- b ]喹啉，a啶和嘧啶并[4,5- b ]喹啉）。