Location

Ac Pit

Advisor(s)

Dr. Denis Chusov

Dr. Oleg Afanasyev

Start Date

30-6-2018 10:00 AM

End Date

30-6-2018 10:15 AM

Abstract

Reduction of nitro compounds lies at the center of most of the major areas of modern chemical industry, such as pharmacy and dye manufacturing. The precursors in these industrial processes predominantly possess multiple functional groups, including those highly susceptible to reduction by most of the currently used reducing agents. Therefore, the non-selective methods of reduction of precursors result in the loss of such functional groups. Furthermore, common reducing agents can potentially trigger the undesired intramolecular interactions between the substrate molecules and in turn make it impossible to obtain the end product. The rising demand for a cheap and efficient approach to reduction of nitro compounds makes finding an optimal reducing agent increasingly relevant.

In the present research, iron pentacarbonyl was chosen as an efficient and sustainable alternative to the primarily hydrogen-based reducing agents currently in use. Iron pentacarbonyl is a cheap and widely available chemical, which is produced in thousands of tons annually. Unlike the other available reducing agents, iron pentacarbonyl makes the selective and tolerant reduction of nitro compounds with multiple functional groups possible. Therefore, the implementation of iron pentacarbonyl as a reducing agent allows to significantly simplify and reduce the cost of synthesis of a number of pharmaceuticals, such as Cinacalcet, Maraviroc, Pramipexole, and Sertraline.

The primary model used to investigate the reactivity of iron pentacarbonyl was reductive amination of 2-nitrobenzaldehyde with pyrrolidine. We were able to successfully carry out reductive amination of the aldehyde group and the reduction of the nitro group in just one step with high yields.

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Jun 30th, 10:00 AM Jun 30th, 10:15 AM

Reduction of Nitro-Compounds by Iron Pentacarbonyl - New Approach to Drug Precursors

Ac Pit

Reduction of nitro compounds lies at the center of most of the major areas of modern chemical industry, such as pharmacy and dye manufacturing. The precursors in these industrial processes predominantly possess multiple functional groups, including those highly susceptible to reduction by most of the currently used reducing agents. Therefore, the non-selective methods of reduction of precursors result in the loss of such functional groups. Furthermore, common reducing agents can potentially trigger the undesired intramolecular interactions between the substrate molecules and in turn make it impossible to obtain the end product. The rising demand for a cheap and efficient approach to reduction of nitro compounds makes finding an optimal reducing agent increasingly relevant.

In the present research, iron pentacarbonyl was chosen as an efficient and sustainable alternative to the primarily hydrogen-based reducing agents currently in use. Iron pentacarbonyl is a cheap and widely available chemical, which is produced in thousands of tons annually. Unlike the other available reducing agents, iron pentacarbonyl makes the selective and tolerant reduction of nitro compounds with multiple functional groups possible. Therefore, the implementation of iron pentacarbonyl as a reducing agent allows to significantly simplify and reduce the cost of synthesis of a number of pharmaceuticals, such as Cinacalcet, Maraviroc, Pramipexole, and Sertraline.

The primary model used to investigate the reactivity of iron pentacarbonyl was reductive amination of 2-nitrobenzaldehyde with pyrrolidine. We were able to successfully carry out reductive amination of the aldehyde group and the reduction of the nitro group in just one step with high yields.

 

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