A New Synthetic Route to Heteroanthracenes

A New Synthetic Route to Heteroanthracenes Full article

Journal

European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690

Output data

Year: 2018, Volume: 2018, Number: 10, Pages: 1265-1273 Pages count : 9 DOI: 10.1002/ejoc.201701689

Tags

Synthetic methods; Macrocycles; Cyclotrimerization; Nitrogen heterocycles; Hydrazones

Authors

Glukhacheva Vera S. ¹ , Il'yasov Sergey G. ¹ , Obraztsov Alexander A. ¹ , Gatilov Yuri V. ^2,3 , Eltsov Ilia V. ³

Affiliations

1	(Данные Web of science) Russian Acad Sci, Inst Problems Chem & Energet Technol, Siberian Branch, Biisk 659322, Russia
2	(Данные Web of science) Russian Acad Sci NIOCh SB RAS, NN Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Branch, Novosibirsk 630090, Russia
3	(Данные Web of science) Novosibirsk State Univ, Novosibirsk 630090, Russia

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 degrees C as well as by the hydrolytic decomposition of glyoxal bis(nitrosemicarbazone) in aqueous medium at 70 degrees 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.

Glukhacheva V.S. , Il'yasov S.G. , Obraztsov A.A. , Gatilov Y.V. , Eltsov I.V.
A New Synthetic Route to Heteroanthracenes
European Journal of Organic Chemistry. 2018. V.2018. N10. P.1265-1273. DOI: 10.1002/ejoc.201701689 WOS Scopus РИНЦ

Published print:	Mar 14, 2018
Published online:	Mar 14, 2018

Web of science	WOS:000427473000011
Scopus	2-s2.0-85043693108
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