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A New Synthetic Route to Heteroanthracenes
Author(s) -
Glukhacheva Vera S.,
Il'yasov Sergey G.,
Obraztsov Alexander A.,
Gatilov Yuri V.,
Eltsov Ilia V.
Publication year - 2018
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.201701689
Subject(s) - glyoxal , chemistry , hydrazone , dimer , tautomer , aqueous solution , hydrolysis , derivative (finance) , lactam , anthracene , aqueous medium , stereochemistry , medicinal chemistry , organic chemistry , polymer chemistry , financial economics , economics
In this report, we describe the synthesis of 2,3,4a,6,7,8a,9,10‐octaaza‐4,8‐dioxo‐3,4,4a,7,8,8a,9,9a,10,10a‐decahydroanthracene, an octaaza derivative of reduced anthracene, through the reaction of glyoxal bis(nitrosemicarbazone) with glyoxal bis(hydrazone) in aqueous medium at 70 °C as well as by the hydrolytic decomposition of glyoxal bis(nitrosemicarbazone) in aqueous medium at 70 °C in a one‐pot transformation. The structure of the resultant compound was confirmed by physicochemical analytical methods and X‐ray diffraction. We also obtained the first representative of the cyclic monohydrazone dimer 1,2,4,5,8,9,11,12‐octaazacyclotetradeca‐5,7,12,14‐tetraene‐3,10‐dione, which exists as lactam and lactim tautomers, through the reaction of glyoxal bis(nitrosemicarbazone) with glyoxal bis(hydrazone) in alkaline aqueous medium.