2-chloro-3-iodo-1-azaazulene | 503865-68-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 2-chloro-3-iodo-1-azaazulene
• 英文别名: 2-Chloro-3-iodocyclohepta[b]pyrrole；2-chloro-3-iodocyclohepta[b]pyrrole
• CAS: 503865-68-7
• 化学式: C₉H₅ClIN
• 分子量: 289.503
• InChiKey: UKVULMWRAVIGDW-UHFFFAOYSA-N

物化性质

• 沸点：
  323.6±42.0 °C(Predicted)
• 密度：
  1.90±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-chloro-3-iodo-1-azaazulene 、 2-(4,4,5,5-四甲基-1,3,2-二杂氧戊硼烷-2-基)苯酚 在 bis-triphenylphosphine-palladium(II) chloride 、 caesium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以60%的产率得到cyclohepta[d]benzo[4,5]furano[2,3-b]pyrrole
  参考文献：
  名称：

  Synthesis of Novel Benzofuran Fused 1-Azaazulene Derivative by Tandem Intermolecular Suzuki Coupling/Intramolecular Buchwald-Hartwig Type Coupling

  摘要：

  Synthesis of benzofuran fused 1-azaazulene derivative (cyclohepta[d]benzo[4,5]furano[2,3-b]pyrrole) (4) was achieved successfully by tandem intermolecular Suzuki coupling/intramolecular Buchwald-Hartwig type coupling of 2-chloro-3-iodo-1-azaazulene with 2-hydroxyphenylboronic acid pinacolate in the presence of Pd catalyst. The compound 4 was also obtained by the reaction of 2-chloro-1-azaazulene with 2-iodophenol in the presence of Pd catalyst in one pot. It was considered that the obtained tetra-cyclic heterocycles would consist 18 pi peripheral conjugated system by the studies of UV/Vis spectra and H-1 NMR spectra, together with DFT calculation.

  DOI：

  10.3987/com-13-s(s)59
• 作为产物：
  描述：

  2-chloro-1-azaazulene 在 N-碘代丁二酰亚胺 作用下， 生成 2-chloro-3-iodo-1-azaazulene
  参考文献：
  名称：

  Synthesis and Reactions of 3- and 8-Ethynyl-1-azaazulenes

  摘要：

  DOI：

  10.3987/com-02-s(m)18

文献信息

• 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.
• Synthesis of Aryl Conjugated (1-Azaazulenyl)acetylenes and Facile Synthesis of Thiophene Fused 1-Azaazulenes
  作者：Noritaka Abe、Yohei Harada、Yukiko Imachi、Hiroyuki Fujii、Akikazu Kakehi、Motoo Shiro

  DOI：10.3987/com-06-s(k)37

  日期：——

  3-Ethynyl-1-azaazulene derivatives were obtained by Sonogashira-Hagihara reaction of 3-iodo-2-chloro-1-azaazulenes, and 2-(phenylethynyl)-1-azaazulenes were obtained by the reaction of 2-bromo-1-azaazulenes. Glaser reaction of 2-chloro-3-ethynyl-1-azaazulenes gave 1,4-bis(2-chloro-1-azaazulen-3-yl)-1,3-butadiyne. Treatment of 2-chloro-3-ethynyl-1-azaazulene derivatives with sodium hydrosulfide gave corresponding 1-thia-9-azacyclopent[a]azulene derivatives in good yield.
• Synthesis of Novel Benzofuran Fused 1-Azaazulene Derivative by Tandem Intermolecular Suzuki Coupling/Intramolecular Buchwald-Hartwig Type Coupling
  作者：Hiroyuki Fujii、Noritaka Abe、Kazuya Sanada、Yu Kawai、Reiko Ikeda、Takeo Konakahara

  DOI：10.3987/com-13-s(s)59

  日期：——

  Synthesis of benzofuran fused 1-azaazulene derivative (cyclohepta[d]benzo[4,5]furano[2,3-b]pyrrole) (4) was achieved successfully by tandem intermolecular Suzuki coupling/intramolecular Buchwald-Hartwig type coupling of 2-chloro-3-iodo-1-azaazulene with 2-hydroxyphenylboronic acid pinacolate in the presence of Pd catalyst. The compound 4 was also obtained by the reaction of 2-chloro-1-azaazulene with 2-iodophenol in the presence of Pd catalyst in one pot. It was considered that the obtained tetra-cyclic heterocycles would consist 18 pi peripheral conjugated system by the studies of UV/Vis spectra and H-1 NMR spectra, together with DFT calculation.
• Synthesis and Reactions of 3- and 8-Ethynyl-1-azaazulenes
  作者：Noritaka Abe、Hiroyuki Fujii、Noritaka Umeda、Akikazu Kakehi

  DOI：10.3987/com-02-s(m)18

  日期：——