Novel electrophilic aromatic iodine substitution of some naphtholic Schiff bases

Schiff bases bearing phenyl and pyridyl groups were synthesized by condensation of appropriate amines with 2-hydroxynaphthaldehyde. These Schiff bases were obtained as colored crystalline solids. The proton NMR spectra of these compounds showed a doublet for the NH protons indicating a keto tautomer for these Schiff bases. The pyridyl-substituted Schiff bases containing hydroxyl moiety were found to show the most downfield shift for the NH protons in DMSO solvent, and this was rationalized due to the formation of a six- and five-membered ring using hydrogen bonds for these two compounds. Correspondingly, the olefinic proton of the Schiff bases is also found to be a doublet due to coupling to the amine proton. These Schiff bases exhibited thermochromic properties. Detailed NMR spectral analysis for both the phenyl- and pyridyl-substituted Schiff bases is presented.

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Structural investigation on phenyl‐ and pyridin‐2‐ylamino(methylene)naphthalen‐2(3H)‐one. Substituent effects on the NMR chemical shifts

Venkatachalam

Pierens

Campitelli

et al. 2010

Magnetic Reson in Chemistry

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Selective O-deallylation of dihydropyrazoles by molecular iodine in the presence of active N-allyl and formyl groups

2012

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Facile aromatization of 3,4-dihydropyrimidin-2(1H)-ones (DHPMs) by iodine

Kodape

Aswar

Gawhale³

et al. 2012

Chinese Chemical Letters

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Novel electrophilic aromatic iodine substitution of some naphtholic Schiff bases

Cited by 4 publications

References 21 publications

Structural investigation on phenyl‐ and pyridin‐2‐ylamino(methylene)naphthalen‐2(3H)‐one. Substituent effects on the NMR chemical shifts

Structural investigation on phenyl‐ and pyridin‐2‐ylamino(methylene)naphthalen‐2(3H)‐one. Substituent effects on the NMR chemical shifts

Selective O-deallylation of dihydropyrazoles by molecular iodine in the presence of active N-allyl and formyl groups

Facile aromatization of 3,4-dihydropyrimidin-2(1H)-ones (DHPMs) by iodine

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