Presentation Title

Base-catalyzed Synthesis of Indoles

Faculty Mentor

Jesus Cordova Guerrero

Start Date

23-11-2019 10:45 AM

End Date

23-11-2019 11:30 AM

Location

214

Session

poster 4

Type of Presentation

Poster

Subject Area

physical_mathematical_sciences

Abstract

Indoles are heterocyclic compounds that are commonly found in nature and play a significant biological role when isolated and combined with other compounds or organic molecules. This allows for diverse applications of indoles in drug synthesis, medicine, and pharmacology. The ability of indoles to inhibit tumor growth and block biological receptors by replicating the structure of an organism’s proteins makes them an ideal compound for the treatment of certain cancers, infectious diseases, and psychological disorders. There are already a variety of known methods to synthesize indoles, such as the Fischer synthesis or reduction of sp3 hybridized carbon-hydrogen bonds through the treatment of 0-nitrostyrenes with aqueous titanium chloride. However, these methods utilize toxic and dangerous starting materials.

The goal of this research is to determine an efficient synthesis of indoles in two steps using commercially available starting materials via a Suzuki coupling reaction followed by a base-catalyzed Michael Addition-oxidation. This process will represent an effective method for the synthesis of indoles and use less toxic starting materials than the currently used methods. Also, it could potentially reduce the cost of production for medications containing this functional group. Previously, a tetrahydrocarbazole derivative of the desired indole product was synthesized in two steps. A successful Suzuki coupling reaction between 2-phenylvinyl boronic acid and 2-iodoaniline was achieved in 94% yield. The resulting bicyclic molecule was subjected to several different cyclization conditions which consist of a base, solvent, and oxidizing agent. None of the cyclization conditions attempted were successful in creating the desired indole product. Future reactions will include a Suzuki coupling between 2-aminobenzene boronic acid and 3-bromo-4-ethoxy-1,1,1-trifluorobut-3-en-1-one to complete the indole synthesis in one step by combining the Suzuki coupling reaction with the Michael addition.

This document is currently not available here.

Share

COinS
 
Nov 23rd, 10:45 AM Nov 23rd, 11:30 AM

Base-catalyzed Synthesis of Indoles

214

Indoles are heterocyclic compounds that are commonly found in nature and play a significant biological role when isolated and combined with other compounds or organic molecules. This allows for diverse applications of indoles in drug synthesis, medicine, and pharmacology. The ability of indoles to inhibit tumor growth and block biological receptors by replicating the structure of an organism’s proteins makes them an ideal compound for the treatment of certain cancers, infectious diseases, and psychological disorders. There are already a variety of known methods to synthesize indoles, such as the Fischer synthesis or reduction of sp3 hybridized carbon-hydrogen bonds through the treatment of 0-nitrostyrenes with aqueous titanium chloride. However, these methods utilize toxic and dangerous starting materials.

The goal of this research is to determine an efficient synthesis of indoles in two steps using commercially available starting materials via a Suzuki coupling reaction followed by a base-catalyzed Michael Addition-oxidation. This process will represent an effective method for the synthesis of indoles and use less toxic starting materials than the currently used methods. Also, it could potentially reduce the cost of production for medications containing this functional group. Previously, a tetrahydrocarbazole derivative of the desired indole product was synthesized in two steps. A successful Suzuki coupling reaction between 2-phenylvinyl boronic acid and 2-iodoaniline was achieved in 94% yield. The resulting bicyclic molecule was subjected to several different cyclization conditions which consist of a base, solvent, and oxidizing agent. None of the cyclization conditions attempted were successful in creating the desired indole product. Future reactions will include a Suzuki coupling between 2-aminobenzene boronic acid and 3-bromo-4-ethoxy-1,1,1-trifluorobut-3-en-1-one to complete the indole synthesis in one step by combining the Suzuki coupling reaction with the Michael addition.