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New synthetic routes to heterocycles from acetylides

  • Full or part time
  • Application Deadline
    Applications accepted all year round
  • Self-Funded PhD Students Only
    Self-Funded PhD Students Only

Project Description

Heterocyclic compounds are ubiquitous: over 90% of all new drugs contain heterocyclic rings, for example. The development of reactions that can furnish excellent yields of heterocyclic compounds under mild conditions and with maximum efficiency remains a desirable objective of organic chemistry.

This project will build on our recent investigations into the synthesis of heterocycles from acetylides and heterocumulenes such as CS2, PhNCS, and PhNCO. It appears that a wide structural variety of different compounds can be accessed depending on the exact conditions used. Typical examples of compounds prepared are 1,2-dithiole-3-thiones, thiazolidines and 3-arylaminomaleimides. Since these publications listed below we have isolated further interesting and previously unknown heterocyclic systems by exploring the influence of substituents, quenching agents, counter-ion and order of reagent addition.

This project will continue this work initially by examining the cyclisation of acetylides with a wider variety of heterocumulenes, and characterisation of the products by spectroscopic and crystallographic techniques. If appropriate, testing of the pharmacological capabilities of the resulting compounds and their potential as ligands in transition metal complexes will be explored.
This project is primarily organic synthesis, including some organometallic chemistry.

Funding Notes

This is a self-funded project. Applicants should have, or expect to gain, a 2.1 degree in an appropriate subject. Informal enquiries may be made by contacting Dr. Morris (e-mail , telephone 0114 2229363).

References

Tetrahedron Letters 2014, 55, 5283.
Tetrahedron Letters 2016, 57, 1328.
Tetrahedron Letters 2017, 58, 1695.

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