May 10, 2017
Synthesis of 2-amino- and 2-arylazoazulenes via nucleophilic aromatic substitution of 2-chloroazulenes with amines and arylhydrazines.
Organic & biomolecular chemistry
- ,
- ,
- ,
- ,
- ,
- ,
- ,
- ,
- Volume
- 15
- Number
- 18
- First page
- 3917
- Last page
- 3923
- Language
- English
- Publishing type
- Research paper (scientific journal)
- DOI
- 10.1039/c7ob00691h
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.
- Link information
- ID information
-
- DOI : 10.1039/c7ob00691h
- ISSN : 1477-0520
- Pubmed ID : 28426084
- Web of Science ID : WOS:000401147200015