2-chloro-8-(2-pyridyl)-1-azaazulene | 797057-42-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-chloro-8-(2-pyridyl)-1-azaazulene
• 英文别名: Cyclohepta[b]pyrrole, 2-chloro-8-(2-pyridinyl)-；2-chloro-8-pyridin-2-ylcyclohepta[b]pyrrole
• CAS: 797057-42-2
• 化学式: C₁₄H₉ClN₂
• 分子量: 240.692
• InChiKey: WSTPBEWMORFHEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-溴吡啶 、 2-chloro-8-(2-pyridyl)-1-azaazulene 在 正丁基锂 、 邻四氯苯醌 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 17.25h， 以58%的产率得到2-chloro-6,8-di(2-pyridyl)-1-azaazulene
  参考文献：
  名称：

  Synthesis of [Poly(2-pyridyl)-Substituted]-1-azaazulenes

  摘要：

  2-(2-Pyridyl)-1-azaazulenes were derived from 2-bromo- or 2-iodo-1-azaazulenes and 3-(2-pyridyl)-1-azaazulenes were derived from 3-iodo-1-azaazulenes by Suzuki coupling. Reaction of 3-iodo-1-azaazulenes with B(NPDEA) gave corresponding 3-(2-pyridyl)-1-azaazulenes together with 3-borylated-2-chloor-1-azaazulene (9a) or 3,3'-bi(2-methoxy-1-azaazulene) (10b). Reactions of 8-(2-pyridyl)-1-azaazulene with 2-pyridyllithium gave 4,8-di(2-pyridyl)- and 6,8-di(2-pyridyl)-1-azaazulenes. Reactions of 4,8-di(2-pyridyl)-1-azaazulene with 2-pyridyl lithium gave 4,6,8-tri(2-pyridyl)-1-azaazulene. The reactivity of the seven-menbered ring is C8 > C6 > C4. Reaction of 3-(2-pyridyl)-1-azaazulenes with 2-pyridyllithium gave 3,4-di(2-pyridyl)- and 3,8-di(2-pyridyl)-1-azaazulenes.

  DOI：

  10.3987/com-08-s(f)8
• 作为产物：
  描述：

  2-溴吡啶 、 2-chloro-1-azaazulene 以73%的产率得到2-chloro-8-(2-pyridyl)-1-azaazulene
  参考文献：
  名称：

  Effective Methods for Introducing Some Aryl and Heteroaryl Substituent onto 1-Azaazulene Nuclei

  摘要：

  Introduction of aryl and heteroaryl groups onto 1-azaazulene ring was achieved by addition-elimination reaction and Suzuki coupling. Reaction of 2-chloro-1-azaazulenes with 2-aryllithium and 2-heteroaryllithium followed by dehydrogenation with o-chloranil gave 8-aryl- and 8-heteroaryl-2-chloro-1-azaazulene in good yields. Suzuki coupling of 3-iodo-1-azaazulenens with phenylboronic acid in the presence of Pd catalyst afforded 3-phenyl-1-azaazulenes in excellent yield. Suzuki coupling of 2-bromo-1-azaazulenes with phenylboronic acid gave 2-phenyl-1-azaazulenes. Suzuki coupling of 2,3-dibromo-1-azaazulene with phenylboronic acid preferentially occurred at C-2. Reaction of 3-iodo-1-azaazulene with bis(pinacolato)diboron produced 3,3'-bis(1-azaazulene) derivative.

  DOI：

  10.3987/com-05-s(k)10

文献信息

• Synthesis of 2-Chloro-8-(2-pyridyl)-1- azaazulene and Its Metal Complexes
  作者：Noritaka Abe、Eri Hashimoto、Hiroyuki Fujii、Yoshiko Murakami、Shoji Tagashira、Akikazu Kakehi

  DOI：10.3987/com-04-10182

  日期：——

  Reaction of 2-chloro-1-azaazulenes with 2-pyridyllithium followed by dehydrogenation by chloranil gave 8-(2-pyridyl) -1-azaazulene (2). Formation of metal complexes (M = Cu, Fe, Pd) of 2 was achieved. The reaction of 2 with Cu(I) gave 1:1 -complex (3) and 2:1-complex (4). Complex (3) was deduced to have a polymeric chain structure with the copper center is +1. The ESR spectrum study of 4 showed that the copper center is +2. The structure of 4 was decided by X-Ray structural analysis and it is shown that the complex takes a trigonal bi-pyramidal structure.
• Effective Methods for Introducing Some Aryl and Heteroaryl Substituent onto 1-Azaazulene Nuclei
  作者：Noritaka Abe、Megumi Tanaka、Takeshi Maeda、Hiroyuki Fujii、Akikazu Kakehi

  DOI：10.3987/com-05-s(k)10

  日期：——

  Introduction of aryl and heteroaryl groups onto 1-azaazulene ring was achieved by addition-elimination reaction and Suzuki coupling. Reaction of 2-chloro-1-azaazulenes with 2-aryllithium and 2-heteroaryllithium followed by dehydrogenation with o-chloranil gave 8-aryl- and 8-heteroaryl-2-chloro-1-azaazulene in good yields. Suzuki coupling of 3-iodo-1-azaazulenens with phenylboronic acid in the presence of Pd catalyst afforded 3-phenyl-1-azaazulenes in excellent yield. Suzuki coupling of 2-bromo-1-azaazulenes with phenylboronic acid gave 2-phenyl-1-azaazulenes. Suzuki coupling of 2,3-dibromo-1-azaazulene with phenylboronic acid preferentially occurred at C-2. Reaction of 3-iodo-1-azaazulene with bis(pinacolato)diboron produced 3,3'-bis(1-azaazulene) derivative.
• Synthesis of [Poly(2-pyridyl)-Substituted]-1-azaazulenes
  作者：Noritaka Abe、Tomoyuki Ariyoshi、Satomi Watarai、Shoji Tagashira、Tomonori Noda、Yoshiko Murakami、Hiroyuki Fujii

  DOI：10.3987/com-08-s(f)8

  日期：——

  2-(2-Pyridyl)-1-azaazulenes were derived from 2-bromo- or 2-iodo-1-azaazulenes and 3-(2-pyridyl)-1-azaazulenes were derived from 3-iodo-1-azaazulenes by Suzuki coupling. Reaction of 3-iodo-1-azaazulenes with B(NPDEA) gave corresponding 3-(2-pyridyl)-1-azaazulenes together with 3-borylated-2-chloor-1-azaazulene (9a) or 3,3'-bi(2-methoxy-1-azaazulene) (10b). Reactions of 8-(2-pyridyl)-1-azaazulene with 2-pyridyllithium gave 4,8-di(2-pyridyl)- and 6,8-di(2-pyridyl)-1-azaazulenes. Reactions of 4,8-di(2-pyridyl)-1-azaazulene with 2-pyridyl lithium gave 4,6,8-tri(2-pyridyl)-1-azaazulene. The reactivity of the seven-menbered ring is C8 > C6 > C4. Reaction of 3-(2-pyridyl)-1-azaazulenes with 2-pyridyllithium gave 3,4-di(2-pyridyl)- and 3,8-di(2-pyridyl)-1-azaazulenes.