: 88-97
Lviv Polytechnic National University
Lviv Polytechnic National University
Lviv Polytechnic National University
Lviv Polytechnic National University
Lviv Polytechnic National University

The nucieophilic properties of amino group in the 2-position of the 1,4-naphthoquinone
in the reactions of alkylation, acylation, and also in interaction with sulfinyl chlorides and
sulfonyl chlorides in comparison with the nucieophilic properties of the amino groups in the 6-
and 7-position has been investigated. It was found that in the presence of an amino group in
the molecule of substituted 1,4-naphthoquinone there is a displacement of the electron density
in the direction of the 1,4-naphthoquinone ring with an appropriate charge change on the
carbon atoms in a certain position, thus the reactivity of the amino group in the alkylation
reaction is highest at the 7-th carbon atom, some the lower activity of the amino group in the 6-
th position and the lowest in the 2-position of the 1,4-naphthoquinone

1. F. Giroud, R. Milton, B. Tan, et al. Simplifying Enzymatic Biofuel Cells: Immobilized
Naphthoquinone as a Biocathodic Orientational Moiety and Bioanodic Electron Mediator // ACS Catal. –
2015, 5, P. 1240–1244. 2. V. Tandon, D. Yadav, R. Singh, et al. Synthesis and biological evaluation of
novel (L)-α-amino acid methyl ester, heteroalkyl, and aryl substituted 1,4-naphthoquinone derivatives as
antifungal and antibacterial agents // Bioorg. Med. Chem. Letters – 2005. – No. 15. – P. 5324–5328.
3. S. Sandur, H. Ichikawa, G. Sethi et al. Plumbagin (5-Hydroxy-2-methyl-1,4-naphthoquinone) Suppresses
NF-B Activation and NF-kB-regulated Gene Products Through Modulation of p65 and IkBα Kinase
Activation, Leading to Potentiation of Apoptosis Induced by Cytokine and Chemotherapeutic Agents //
J. Biological Chemistry – 2006. – No. 25. – Vol. 281. – P. 17023–17033. 4. Fries K., Pense W., Peters O.
Uber lin Benzo-p-thiazino-chinone // Ber. – 1928. – No. 61. – P. 1395–1401. 5. Бучкевич І. Р., Платонов
М. О., Стасевич М. В., Лубенець В. І., Мусянович Р. Я. Синтез нових азотовмісних похідних 2,3,6-
трихлор-1,4-нафтохінону // Вісник Національного університету „Львівська політехніка” Хімія,
технологія речовин та їх застосування. – 2009. – № 644. – С. 111–114. 6. Шишкина Р. П., Маматюк
В. П., Фокин Е. И. Сульфирование и сульфохлорирование 2,3-дихлор-1,4-нафтохинона. // Изв. Сиб.
Отд. АН СССР. Сер. Химия. – 1984. – № 3. – C. 855–857. 7. Pingaew R., Prachayasittikul V.,
Worachartcheewan A. et al. Novel 1,4-naphthoquinone-based sulfonamides: synthesis, QSAR, anticancer
and antimalarial studies / Euro. J.Med. Chem. – 2015. – No. 103. – P. 446–459. 8. Buchkevych I.,
Stasevych M., Musyanovych R. et al. S- and N,S-Containing heterocycles based on sulfenyl chlorides of
substituted 1,4-naphthoquinone // Chemistry of Heterocyclic Compounds. – 2010. – Vol. 46(4). –
P. 502–504. 9. Satheshkumar A., Elango K. Spectroscopic and theoretical studies on the nucleophilic
substitution of 2,3-dichloronaphthoquinone with para-substituted anilines in solid state via initial charge
transfer complexation // Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. –
2012. – Vol. 98. – P. 378–383. 10. Ластухін Ю. О., Воронов С. А. Органічна хімія. – Львів: Центр
Європи, 2001. – 864 с. 11. Bolibrukh K., Polovkovych S., Khoumeri O. et al. Synthesis and anti-platelet
activity of thiosulfonate derivatives containing a quinone moiety // Scientia Pharmaceutica. – 2015. –
Vol. 83 (2). – P. 221–231. 12. PASS (Prediction of Activity Spectra for Substances) [електронний ресурс] /
режим доступу до ресурсу: Online/.