7-amino-6-cyano-5-methylthio-s-triazolo<1,5-a>pyrimidine | 98190-26-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三唑并嘧啶类
• 英文名称: 7-amino-6-cyano-5-methylthio-s-triazolo<1,5-a>pyrimidine
• 英文别名: 7-Amino-5-methylsulfanyl-[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitrile
• CAS: 98190-26-2
• 化学式: C₇H₆N₆S
• 分子量: 206.231
• InChiKey: FVGZQLZHGMBNIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7-amino-6-cyano-5-methylthio-s-triazolo<1,5-a>pyrimidine 、 丁炔二酸二乙酯 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 以23%的产率得到4H-1,4,7,8,10,10a-Hexaaza-cyclopenta[a]phenalene-2,3,5,6-tetracarboxylic acid tetraethyl ester
  参考文献：
  名称：

  Synthesis of Polycyclic Nitrogen-containing Heterocycles: One Pot Formation of 1,6-Naphthyridine Ring System by Reaction of Amino-cycano-methylyhio-heterocycles with Dialkyl Acetylenedicarboxylates

  摘要：

  The reaction of 5-amino-6-cyano-1,3-dimethyl-7-methylthiopyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (1c) with dimethyl acetylenedicarboxylate (DMAD) in the presence of potassium carbonate in dimethyl sulfoxide gave tetramethyl 8,9,10,11-tetrahydro-8,10-dimethyl-9,10-dioxo-4H-pyrimido[4',5':5,6]pyrido[2,3,4-cb][1,6]naphthyridine-2,3,5,6-tetracarboxylate (2c). The reaction of other heterocycles bearing amino, cyano, and methylthio groups with DMAD or DEAD under the same reaction conditions gave the corresponding tetracyclic heterocycles containing the fundamental 1,6-naphthyridine ring system.

  DOI：

  10.3987/com-95-s13
• 作为产物：
  描述：

  3-氨基-1,2,4-三氮唑 、 [双(甲硫基)亚甲基]丙烷二腈 反应 1.5h， 以70%的产率得到7-amino-6-cyano-5-methylthio-s-triazolo<1,5-a>pyrimidine
  参考文献：
  名称：

  Pyrimidine and fused pyrimidine derivatives. III. Synthesis of s-triazolo(1,5-a)pyrimidine derivatives by using ketene dithioacetals.

  摘要：

  3-amino-s-triazole (1) 与酮烯二硫代乙醛 (2) 反应得到 5-methylthio-s-triazolo [1, 5-a] pyrimidine 衍生物，产率令人满意。此外，还介绍了 7-氨基-s-三唑并[1, 5-a]嘧啶衍生物的合成。

  DOI：

  10.1248/cpb.33.962

文献信息

• Pyrimidine and fused pyrimidine derivatives. III. Synthesis of s-triazolo(1,5-a)pyrimidine derivatives by using ketene dithioacetals.
  作者：YOSHINORI TOMINAGA、SHUICHIRO SAKAI、SHINYA KOHRA、JUNKO TSUKA、YOSHIRO MATSUDA、GORO KOBAYASHI

  DOI：10.1248/cpb.33.962

  日期：——

  The reaction of 3-amino-s-triazole (1) with ketene dithioacetals (2) gave 5-methylthio-s-triazolo [1, 5-a] pyrimidine derivatives in satisfactory yields. The synthesis of 7-amino-s-triazolo-[1, 5-a] pyrimidine derivatives is also described.

  3-amino-s-triazole (1) 与酮烯二硫代乙醛 (2) 反应得到 5-methylthio-s-triazolo [1, 5-a] pyrimidine 衍生物，产率令人满意。此外，还介绍了 7-氨基-s-三唑并[1, 5-a]嘧啶衍生物的合成。
• Synthesis of polycyclic nitrogen-containing heterocyclic: One pot formation of 1,6-naphthyridine ring system by reaction of amino-cyano-methylthio-heterocycles with dialkyl acetyeledicarboxylates
  作者：Yoshinori Tominaga、Kenichi Nomoto、Noriko Yoshioka

  DOI：10.1002/jhet.5570380518

  日期：2001.9

  Reaction of 3-amino-3-methylthio-2-cyanoacrylonitrile (1) with excess dimethyl acetylenedi-carboxylate(DMAD) in the presence of potassium carbonate in dimethyl sulfoxide gave a novel tricyclic heterocycle, hexamethyl lH-1,4,7-triazaphenalene-2,3,5,6,8,9-hexacarboxylate (5a). When one equivalent of DMAD was used in this reaction, dimethyl 4-amino-3-cyano-2-methylthiopyridine-5,6-dicarboxylate (3a),

  在碳酸钾存在下，使3-氨基-3-甲硫基-2-氰基丙烯腈（1）与过量的乙炔基二羧酸二甲酯（DMAD）反应，生成新的三环杂环，六甲基l H -1,4,7-三氮杂萘-2,3,5,6,8,9-六羧酸盐（5a）。当在该反应中使用一当量的DMAD时，获得4-氨基-3-氰基-2-甲基硫代吡啶二甲基-5,6-二羧酸二甲酯（3a），其为5a的关键中间体。
• TOMINAGA, YOSHINORI;SAKAI, SHUICHIRO;KOHRA, SHINYA;TSUKA, JUNKO;MATSUDA, +, CHEM. AND PHARM. BULL., 1985, 33, N 3, 962-970
  作者：TOMINAGA, YOSHINORI、SAKAI, SHUICHIRO、KOHRA, SHINYA、TSUKA, JUNKO、MATSUDA, +

  DOI：——

  日期：——
• Synthesis of Polycyclic Nitrogen-containing Heterocycles: One Pot Formation of 1,6-Naphthyridine Ring System by Reaction of Amino-cycano-methylyhio-heterocycles with Dialkyl Acetylenedicarboxylates
  作者：Yoshinori Tominaga、Noriko Yoshioka

  DOI：10.3987/com-95-s13

  日期：——

  The reaction of 5-amino-6-cyano-1,3-dimethyl-7-methylthiopyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (1c) with dimethyl acetylenedicarboxylate (DMAD) in the presence of potassium carbonate in dimethyl sulfoxide gave tetramethyl 8,9,10,11-tetrahydro-8,10-dimethyl-9,10-dioxo-4H-pyrimido[4',5':5,6]pyrido[2,3,4-cb][1,6]naphthyridine-2,3,5,6-tetracarboxylate (2c). The reaction of other heterocycles bearing amino, cyano, and methylthio groups with DMAD or DEAD under the same reaction conditions gave the corresponding tetracyclic heterocycles containing the fundamental 1,6-naphthyridine ring system.