One-pot multicomponent synthesis of piperidinium 3,3'-(arylmethylene) bis (2-hydroxynaphthalene-1,4-diones): NMR spectroscopic and X-ray~structure characterization

Authors

MARYAM FATAHPOUR
NOUROLLAH HAZERI
MALEK TAHER MAGHSOODLOU
FATEMEH NOORI SADEH
MOJTABA LSHKARI

DOI

10.3906/kim-1712-52

Abstract

A facile synthesis of piperidinium 3,3'-(arylmethylene) bis (2-hydroxynaphthalene-1,4-dione) analogs as organic salts is described by the one-pot pseudo-four-component reaction between 2-hydroxy-1,4-naphthoquinone, aromatic aldehydes, and piperidine. The single-crystal X-ray diffraction analysis of these systems confirms that the stabilized predominant interactions are N-H\... O and O-H\... O hydrogen bonds. Mild and clean reaction conditions, high atom economy, and operational simplicity of this one-pot multicomponent reaction coupled with excellent yields and no need for column chromatography have transformed this procedure to be a superior synthetic route for the efficient formation of families of naphthoquinone-derived compounds.

Keywords

Organic salts, 2-hydroxy-1, 4-naphthoquinone, crystal structure, hydrogen bonds

First Page

908

Last Page

917

Recommended Citation

FATAHPOUR, MARYAM; HAZERI, NOUROLLAH; MAGHSOODLOU, MALEK TAHER; SADEH, FATEMEH NOORI; and LSHKARI, MOJTABA (2018) "One-pot multicomponent synthesis of piperidinium 3,3'-(arylmethylene) bis (2-hydroxynaphthalene-1,4-diones): NMR spectroscopic and X-ray~structure characterization," Turkish Journal of Chemistry: Vol. 42: No. 3, Article 24. https://doi.org/10.3906/kim-1712-52
Available at: https://journals.tubitak.gov.tr/chem/vol42/iss3/24