Synthesis of Schiff bases between some five-membered heterocyclic aldehydes and thiocarbohydrazide (TCH) and optimization of reaction conditions

2nd International Conference on Chemo and Bioinformatics ICCBIKG 2023 (435-438)

АУТОР(И) / AUTHOR(S): Miljan Bigović, Marija Kaluđerović, Jovana Jovanović, Haris Majstorović, Milica Kosović-Perutović

Е-АДРЕСА / E-MAIL: miljan@ucg.ac.me

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DOI: 10.46793/ICCBI23.435B

САЖЕТАК / ABSTRACT:

The usual way of synthesizing imines (Schiff bases) between carbonyl compounds –aldehydes and ketones – with thiocarbohydrazide (TCH) involves heating them for 3 hours in a mixture of water solvents and ethanol with the addition of a catalytic amount of concentrated hydrochloric acid. Heating in the presence of acid catalysts over a long period of time may be unsuitable for acid-sensitive, labile, reactive or thermally unstable aldehydes, which are prone to polymerization under these conditions. We tested the condensation reaction at room temperature with a series of aldehydes, while maintaining the described ratios (equimolar ratio of aldehydes and TCH), with the addition of a few drops of 36% HCl. The course and completion of the reaction were monitored using infrared spectroscopy (FTIR). The reaction time is longer compared to the heating conditions, while the yields are comparable. We obtained a series of compounds of high degree of purity, satisfactory yield varying from 50-90%, whose structure and purity were confirmed by NMR spectroscopy.

КЉУЧНЕ РЕЧИ / KEYWORDS:

Schiff bases, aldehydes, NMR, carbohydrazides, FTIR

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