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- Title
Synthesis of 1,2‐Dicyano‐3‐arylcycl[3.2.2]azines – First 1,2‐Dicarbonitriles Based on Cyclazine Heterocycle.
- Authors
Starikov, Andrei S.; Kalashnikov, Valery V.; Tarakanov, Pavel A.; Simakov, Anton O.; Simonov, Sergey V.; Tkachev, Valery V.; Yarkov, Alexander V.; Kazachenko, Vladimir P.; Chernyak, Alexander V.; Zhurkin, Fedor E.; Tomilova, Larisa G.; Pushkarev, Victor E.
- Abstract
The first 1,2‐dicarbonitriles have been prepared for cyclazine systems. In particular, a synthetic procedure to 1,2‐dicyano‐3‐arylcycl[3.2.2]azines has been developed. Unexpected chlorination of 3‐arylcycl[3.2.2]azine‐1,2‐dicarboxylic acid derivatives by thionyl chloride at 4‐position was found, which according to theoretical considerations can proceed by the electrophilic (SEAr) mechanism. The compounds are blue fluorophores in 450–480 nm region with quantum yields in toluene of ca. 30 % for non‐chlorinated derivatives, which decrease to 3–4 % for chlorinated ones.
- Subjects
THIONYL chloride; ACID derivatives; AZINES; CHLORINATION; FLUOROPHORES; TOLUENE
- Publication
European Journal of Organic Chemistry, 2020, Vol 2020, Issue 36, p5852
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.202000958