Project Overview

Synthesis of Indole-Fused Heterocycles through a Cascade Thiocyanation and Cyclization

Faculty Sponsor

Liangyong Mei (lmei@colgate.edu)

Department(s)

Chemistry

Abstract

Indole-fused polycycles are important constituents in a wide range of natural products and
pharmaceutical compounds. Thus, finding an efficient protocol for their synthesis is of great significance.
Meanwhile, electrophilic thiocyanation is a convenient way to form thiocyanates, which can be further
converted to other sulfur functional groups. By properly designing the indole substrates, a
thiocyanation/intramolecular cyclization cascade could be realized.
The overarching objective of this project is to develop novel organic synthetic methodologies, particularly
towards the construction of indole-fused heterocycles. We will synthesize a range of indole substrates
with an additional reactive functional group such as alcohol, amine, carboxylic acid etc. and test their
reactivities towards a thiocyanate salt in the presence of an oxidant. Theoretically, an electrophilic
thiocyanation of indole would occur in the first step, which could be followed by an intramolecular
nucleophilic attack, thus forming the polycyclic fused indole derivatives. Other interesting and challenging
transformations regarding these newly synthesized indole substrates will also be explored afterwards.

Student Qualifications

Some Chemistry

Number of Student Researchers

2 students

Project Length

8 weeks


Applications open on 01/03/2022 and close on 02/04/2022


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If you have questions, please contact Karyn Belanger (kgbelanger@colgate.edu).