An expeditious synthetic approach towards the synthesis of Bis-Schiff bases (aldazines) using ultrasound

Khalid M Khan; Waqas Jamil; Nida Ambreen; Muhammad Taha; Shahnaz Perveen; Guillermo A Morales

doi:10.1016/j.ultsonch.2013.12.011

An expeditious synthetic approach towards the synthesis of Bis-Schiff bases (aldazines) using ultrasound

Ultrason Sonochem. 2014 May;21(3):1200-5. doi: 10.1016/j.ultsonch.2013.12.011. Epub 2013 Dec 21.

Authors

Khalid M Khan¹, Waqas Jamil², Nida Ambreen³, Muhammad Taha⁴, Shahnaz Perveen⁵, Guillermo A Morales⁶

Affiliations

¹ H. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan. Electronic address: hassaan2@super.net.pk.
² H. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan; Institute of Advance Research Studies in Chemical Sciences, University of Sindh Jamshoro, Hyderabad 76080, Pakistan.
³ H. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan.
⁴ H. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan; Research Institute of Natural Products for Drug Discovery (RiND), Faculty of Pharmacy, Universiti Teknologi MARA (UiTM), Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor Darul Ehsan, Malaysia.
⁵ PCSIR Laboratories Complex, Karachi, Shahrah-e-Dr. Salimuzzaman Siddiqui, Karachi 75280, Pakistan.
⁶ Morales Consulting LLC, 11474 Perkins Street, Carmel, IN 46032, USA.

PMID: 24398059
DOI: 10.1016/j.ultsonch.2013.12.011

Abstract

Aldazines (Bis-Schiff bases) 1-24 were synthesized using aromatic aldehydes (heterocyclic and benzaldehydes) and hydrazine hydrate under reflux using conventional heating and/or via ultrasound irradiation using BiCl3 as catalyst. Ultrasonication conditions with cat. BiCl3 proved to be an effective, environmentally friendly synthetic procedure. This methodology is robust in the presence of electron donating and electron withdrawing groups affording desired products with high yields (>95%) in just a couple of minutes vs. hours using conventional heating.

Keywords: Aldazines (Bis-Schiff bases); High yielding method; Rapid; Ultrasonication.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Chemistry Techniques, Synthetic / methods*
Electron Transport
Kinetics
Schiff Bases / chemical synthesis*
Ultrasonics*

Substances

Schiff Bases