Synthesis and Structural Analysis of Some New Sulfanyl Amino 1,4-Naphthoquinone Derivatives

Year 2018, Volume: 5 Issue: 1, 149 - 158, 01.09.2017

Hatice Yıldırım

https://doi.org/10.18596/jotcsa.335894

Cited By: 1

Abstract

In this study, some new sulfanyl substituted amino 1,4-naphthoquinone
derivatives which possess two electron donating groups in the amino fragment were
synthesized and their structures were analyzed by spectroscopic techniques. First,
2-chloro-3-[(2,4-dimethoxy
phenyl)amino]naphthalene-1,4-dione (3a)
and 2-chloro-3-[(3,5-dimethoxy phenyl)amino]naphthalene-1,4-dione (3b) were obtained from the reactions of
dichloro 1,4-naphthoquinone (1) with
2,4-dimethoxy phenyl amine and 3,5-dimethoxy phenyl amine. Then the compounds 3a,b
were reacted with aliphatic nucleophiles; ethyl-, propyl- and pentyl mercaptan.
S-Nucleophiles attacked to the carbon atom of 1,4-naphthoquinone core and displaced with the
chlorine atom to create target molecules; 2-aryl amino-3-(ethyl thio)naphthalene-1,4-dione (5a,b), 2-aryl amino-3-(propyl thio)naphthalene-1,4-dione (5c,d),
2-aryl amino-3-(pentyl
thio)naphthalene-1,4-dione (5e,f) derivatives. The structures of synthesized
compounds were proved by utilizing 1D and 2D NMR techniques and also mass
spectra and FTIR data.

Keywords

Sulfanyl and/or arylamine substituted quinones, 1, 4-naphthoquinone, spectroscopic analysis, HMQC/HMBC analysis

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