Novel N,S-Substituted naphthoquinone analogues from aminonaphthoquinones

Halil Ozdinc; Nihal Onul; Funda Ozkok

doi:10.62063/ecb-13

Authors

Halil Ozdinc Istanbul University-Cerrahpaşa, Faculty of Engineering, Department of Chemistry, Avcilar-Istanbul, Türkiye https://orcid.org/0009-0003-3140-6206
Nihal Onul Istanbul University-Cerrahpaşa, Faculty of Engineering, Department of Chemistry, Avcilar-Istanbul, Türkiye https://orcid.org/0000-0002-0101-1735
Funda Ozkok Istanbul University-Cerrahpaşa, Faculty of Engineering, Department of Chemistry, Avcilar-Istanbul, Türkiye https://orcid.org/0000-0001-7263-1977

DOI:

https://doi.org/10.62063/ecb-13

Keywords:

Aminonaphthoquinone, Naphthoquinone, Thionaphthoquinone

Abstract

In this study, novel N,S-substituted naphthaquinone analogues (2, 4, 6, and 8) were synthesized from the reactions of previously known aminonaphthaquinone derivatives (1, 3, 5, and 7) with allyl mercaptan. 2-(allylthio)-3-(4-phenylpiperazin-1-yl)naphthalene-1,4-dione (2), 2-(allylthio)-3-(4-(2-fluorophenyl)piperazin-1-yl)naphthalene-1,4-dione (4), 2-(allylthio) -3-(4-benzylpiperidin-1-yl)naphthalene-1,4-dione (6) and 2-(4-chlorophenylamino)-3-(allylthio)naphthalene-1,4-dione (8) were obtained from the reactions of 2-chloro-3-(4-phenylpiperazin-1-yl)naphthalene-1,4-dione (1), 2-chloro-3-(4-(2-fluorophenyl)piperazin-1-yl)naphthalene-1,4-dione (3), 2-(4-benzylpiperidin-1-yl)-3-chloronaphthalene-1,4-dione (5), and 2-(4-chlorophenylamino) -3-chloronaphthalene-1,4-dione (7) with allyl mercaptan according to the general synthesis procedure. Synthesized new naphthaquinone analogues (2, 4, 6, and 8) were purified by column chromatography. The chemical structures of these novel N,S-substituted naphthaquinone analogues were characterized by spectroscopic methods (FT-IR, NMR, and MS).

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