2024-03-29T09:48:37Z
https://soar-ir.repo.nii.ac.jp/oai
oai:soar-ir.repo.nii.ac.jp:00019889
2022-12-14T04:16:30Z
1169:1170
Synthesis of 2-amino- and 2-arylazoazulenes via nucleophilic aromatic substitution of 2-chloroazulenes with amines and arylhydrazines
Shoji, Taku
Sugiyama, Shuhei
Araki, Takanori
Ohta, Akira
Sekiguchi, Ryuta
Ito, Shunji
Mori, Shigeki
Okujima, Tetsuo
Yasunami, Masafumi
© 2017 Royal Society of Chemistry
The SNAr reaction of 2-chloroazulene derivative 1 with ethoxycarbonyl groups at the 1,3-positions of the azulene ring with several amines afforded the corresponding 2-aminoazulenes 3-9 in excellent yields. 2-Chloroazulene (2) without the electron-withdrawing groups reacted with highly nucleophilic cyclic amines (i.e., morpholine, piperidine and pyrrolidine) under the high-temperature conditions in a sealed tube to produce the corresponding 2-aminoazulenes 10-12 in good yields. 2-Aminoazulenes 10-14 without the electron-withdrawing groups were also obtained in good yields by the treatment of compounds 3-7 with 100% H3PO4, but in the cases of the reaction of 8 and 9 with a secondary amine function, the decomposition of the products resulted. The synthesis of 2-arylazoazulenes 15-18 was also established via the SNAr reaction of 1 with arylhydrazines. The optical and electrochemical properties of the 2-arylazoazulene derivatives were examined by UV/Vis spectroscopy, theoretical calculations and voltammetric experiments.
Article
ORGANIC & BIOMOLECULAR CHEMISTRY. 94(10):3917-3923 (2017)
ROYAL SOC CHEMISTRY
2017-05-14
eng
journal article
AM
http://hdl.handle.net/10091/00020650
https://soar-ir.repo.nii.ac.jp/records/19889
http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?CMD=search&DB=pubmed&term=28426084
28426084
https://doi.org/10.1039/c7ob00691h
10.1039/c7ob00691h
1477-0520
AA1168650X
ORGANIC & BIOMOLECULAR CHEMISTRY
15
18
3917
3923
https://soar-ir.repo.nii.ac.jp/record/19889/files/Org_Biomol_Chem_15_3917-3923.pdf
application/pdf
444.9 kB
2018-06-13