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Synthesis of 1,2‐Dicyano‐3‐arylcycl[3.2.2]azines – First 1,2‐Dicarbonitriles Based on Cyclazine Heterocycle
Author(s) -
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.
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000958
Subject(s) - chemistry , thionyl chloride , azine , toluene , electrophile , organic chemistry , chloride , medicinal chemistry , photochemistry , catalysis
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 (S E Ar) 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.