Investigation of the Sigmatropic Rearrangement of Allenyl Cyanamides

Presenter's Name(s)

Ryan Tan

Conference Year

2024

Abstract

The sigmatropic rearrangement of allenyl cyanamides was studied for its hypothesized utility in effectively producing stable cyclic guanidine products. Investigating pathways to cyclic guanidines has considerable applications in the preparation of biologically active guanidine natural products. The proposed reaction has the unique characteristic of only proceeding above room temperature, unlike similar reactions previously explored. This allows for the purification of the starting material before any reactivity takes place, thereby increasing reaction efficiency. Developing new synthetic pathways to form cyclic guanidines has potential to contribute to the future preparations of guanidine natural products and their related medically important analogs.

Primary Faculty Mentor Name

Jose S. Madalengoitia

Status

Undergraduate

Student College

College of Arts and Sciences

Program/Major

Chemistry

Primary Research Category

Physical Science

Abstract only.

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Investigation of the Sigmatropic Rearrangement of Allenyl Cyanamides

The sigmatropic rearrangement of allenyl cyanamides was studied for its hypothesized utility in effectively producing stable cyclic guanidine products. Investigating pathways to cyclic guanidines has considerable applications in the preparation of biologically active guanidine natural products. The proposed reaction has the unique characteristic of only proceeding above room temperature, unlike similar reactions previously explored. This allows for the purification of the starting material before any reactivity takes place, thereby increasing reaction efficiency. Developing new synthetic pathways to form cyclic guanidines has potential to contribute to the future preparations of guanidine natural products and their related medically important analogs.