Synthesis of 1,2‐Dicyano‐3‐arylcyclazines – First 1,2‐Dicarbonitriles Based on Cyclazine Heterocycle

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, whi...

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Published inEuropean journal of organic chemistry Vol. 2020; no. 36; pp. 5852 - 5856
Main 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
Format Journal Article
LanguageEnglish
Published Weinheim Wiley Subscription Services, Inc 01.09.2020
Subjects
Azines
Chemical compounds
Chlorination
Derivatives
Dicarboxylic acids
Fluorescence
Toluene
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Summary: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.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202000958