Research Article

Gallium (III) triflate-catalyzed synthesis of heterocycles: quinoxalines, 1,5-benzodiazepines and their fluorinated derivatives

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Donald P. and Katherine B. Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, 837 Bloom Walk, Los Angeles, CA 90089-91661, USA.

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Habiba Vaghoo

Donald P. and Katherine B. Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, 837 Bloom Walk, Los Angeles, CA 90089-91661, USA.

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Arthi Venkat

Donald P. and Katherine B. Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, 837 Bloom Walk, Los Angeles, CA 90089-91661, USA.

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Chiradeep Panja

Donald P. and Katherine B. Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, 837 Bloom Walk, Los Angeles, CA 90089-91661, USA.

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Sujith Chacko

Donald P. and Katherine B. Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, 837 Bloom Walk, Los Angeles, CA 90089-91661, USA.

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Thomas Mathew

Donald P. and Katherine B. Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, 837 Bloom Walk, Los Angeles, CA 90089-91661, USA.

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George A Olah

Donald P. and Katherine B. Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, 837 Bloom Walk, Los Angeles, CA 90089-91661, USA.

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Published Online:19 Aug 2009https://doi.org/10.4155/fmc.09.77

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Abstract

Background: The quinoxaline nucleus is a part of several antibiotics, such as echinomycin, levomycin and actinomycin, which are known to inhibit the growth of Gram-positive bacteria and are active against various transplantable tumors. Benzodiazepines are important classes of heterocycles that draw significant interest from the pharmaceutical industry because of their prominent therapeutic value, such as antiviral, antibacterial, anti-inflammatory, antiprotozoaval properties and also as kinase inhibitors. They have also been evaluated as anticancer, anthelmintic, antifungal and insecticidal agents. Results & conclusion: Quinoxalines, benzodiazepines and their fluorinated derivatives have been prepared in excellent yields from the corresponding diamines and diketones using gallium (III) triflate as an efficient and environmentally friendly catalyst, due to its stability, recyclability and minimal toxicity.

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Published online 19 August 2009

Published in print August 2009

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Financial & competing interests disclosure

Support of our work by Loker Hydrocarbon Research Institute is gratefully acknowledged. The authors have no relevant affiliations or financial involvement with any organization or entity with a financial interest in or financial conflict with the subject matter or materials discussed in the manuscript. This includes employment, consultancies, honoraria, stock ownership or options, expert testimony, grants or patents received or pending, or royalties.

No writing assistance was utilized in the production of this manuscript.

Ethical conduct of research

The authors state that they have obtained appropriate institutional review board approval or have followed the principles outlined in the Declaration of Helsinki for all human or animal experimental investigations. In addition, for investigations involving human subjects, informed consent has been obtained from the participants involved.

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