Investigation into Sonogashira reaction on 5-iodo-1-(phenyl/p-halophenyl)imidazole-4-carbonitrile compounds

ABSTRACT

Investigation into Sonogashira reaction on 5-iodo-1-(phenyl/p-halophenyl)imidazole-4-carbonitrile compounds had been developed by introducing an iodo atom at the C-5 position of the imidazole ring of 5-amino-1-(phenyl/p-halophenyl)imidazole-4-carbonitrile compounds. Specifically, 5-iodo-1-(4-iodophenyl)imidazole-4-carbonitrile compound had shown double Sonogashira coupling reactions with two differently substituted iodine along with the formation of two other compounds where an unusual coupling product with self-aggregation property was obtained. In other cases, monocoupling had been observed together with another compound where iodine atom present at C5 position of imidazole was replaced by hydrogen atom.

GRAPHICAL ABSTRACT

KEYWORDS:

• 5-Iodo derivative of AICN
• double scope of Sonogashira reaction
• self-aggregation property
• unusual coupling

Acknowledgments

The author thanks the University of Calcutta for providing laboratory experiment and spectroscopic facilities. Aniruddha Das thanks Prof. (retd) Sibdas Ray, Dr Kaliprasanna Dhara of Chemistry Department, University of Calcutta for their valuable suggestions and support. Single X-ray crystallographic studies had been performed with single-crystal diffractometer facilities sponsored by DST-FIST programme of Department of Chemistry of University of Calcutta. The author expresses deep gratitude to Centre for Research in Nanoscience and Nanotechnology (CRNN) of University of Calcutta for scanning electron microscopic study.

Additional information

Funding

The author thanks the Council of Scientific and Industrial Research (CSIR), New Delhi, India for financial assistance.