Synthesis of some NH- and NH,S- substituted 1,4-quinones | Zendy

Ayşecik Kaçmaz | Zendy

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Synthesis of some NH- and NH,S- substituted 1,4-quinones

Author(s) -

Ayşecik Kaçmaz

Publication year - 2021

Publication title -

turkish journal of chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.239

H-Index - 46

eISSN - 1303-6130

pISSN - 1300-0527

DOI - 10.3906/kim-2011-3

Subject(s) - chemistry , bromine , chloranil , yield (engineering) , nucleophile , medicinal chemistry , ethylamine , chlorine , naphthoquinone , carbon 13 nmr , 1,4 naphthoquinone , quinone , proton nmr , organic chemistry , catalysis , materials science , metallurgy

A series of NH-substituted-1,4-quinones, possessing one, two, three or not chlorine, were synthesized by the reaction between different quinones ( p -chloranil ( 1 ), p -toluquinone ( 2 ), or 2,3-dichloro-1,4-naphthoquinone ( 3 )) and (-)- cis -myrtanylamine ( 5 ) via nucleophilic reactions. Moreover, 2-bromo-1,4-naphthoquinone ( 4 ) was reacted with 2-(methylthio)ethylamine ( 11 ) to produce amino-substituted naphthoquinones ( 12 and 13 ), bearing with bromine and not bromine. In addition, 2-bromo-1,4-naphthoquinone ( 4 ) was reacted with 4'-aminodibenzo-18-crown-6 ( 14 ) and 4'-aminobenzo-18-crown-6 ( 16 ) to yield crown-containing 1,4-naphthoquinones ( 15 and 17 ), respectively. New compounds were characterized, providing 1 H NMR, 13 C NMR, FTIR, MS-ESI, UV/Vis and elemental analysis.

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