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Eco-Friendly and Highly Efficient Synthesis, Including Multigram Synthesis, of Aldehyde Isonicotinoyl Hydrazones Using Sonochemistry

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Background: The isoniazid has been a key compound in first-line tuberculosis (TB) treatment, usually in combination with other drugs. Following on from the use of isoniazid itself, various derivatives of isoniazid have also been investigated as anti-TB agents and other diseases. This work aims to synthesize, multigram scale, salicylaldehyde isonicotinoyl hydrazone from isoniazid and salicylaldehyde, using ultrasound. Additionally, we have been interested in establishing a general, smaller-scale, ultrasonic driven synthesis of arylaldehyde isoniazid N-acylhydrazones, particularly for use in our biological studies.

Methods: A Multiwave Eco-Sonics QR750 ultrasonic generator (20 KHz, 750 W) equipped with a converter/ transducer, and titanium oscillator (horn, diameter = 4 mm) was used for the ultrasonic irradiantion. Compounds were characterized by melting points, infrared spectra, mass spectra (CG/MS), electron microscopy, X-ray powder diffraction, solid-state 13C and solution NMR spectra.

Results: This work describes a green chemistry protocol, multigram scale (ca 4 mole) and highly efficient synthesis utilizing ultrasonic irradiation of salicylaldehyde isonicotinoyl hydrazone, a widely used compound in biological studies. With a short reaction time of 30 min, and a facile work up, involving washing with water, the important bioactive product was obtained in a high yield, 98.7%, and in a high purity 99.43%. Also prepared using ultrasonic irradiation with short reaction times, in high yields and high purities, but on smaller scales, were a series arylaldehyde isoniazid N-acylhydrazones, all of which exhibit promising activity against cancer and tuberculosis. Comparisons with the classical procedures indicate advantages in the ultrasonic irradiated methodology.

Conclusion: We report the high yielding ultrasonic synthesis of pure salicylaldehyde isonicotinoyl hydrazone on a 4 mole scale. In addition, a series of ten isoniazid N-acylhydrazone derivatives has been obtained using ultrasonic irradiation. The ultrasonic procedures are simple, safe, with short reaction times, and produce high yields.
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Keywords: Green chemistry; N-acylhydrazone; SIH; bioactive; isoniazid; sonochemistry

Document Type: Research Article

Publication date: October 1, 2016

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  • Letters in Organic Chemistry publishes original letters on all areas of organic chemistry including synthesis, bioorganic, medicinal, natural products, organometallic, supramolecular, molecular recognition and physical organic chemistry. The emphasis is placed on publishing quality papers very rapidly. Letters are processed rapidly and take full advantage of the Internet technology both for the submission and the review of the manuscripts.
    The journal is essential reading for all organic chemists both in academia and industry.
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