1581682-00-9Relevant academic research and scientific papers
A new route to bicyclo[1.1.1]pentan-1-amine from 1-azido-3-iodobicyclo[1.1. 1]pentane
Goh, Yi Ling,Tam, Eric K.W.,Bernardo, Paul H.,Cheong, Choon Boon,Johannes, Charles W.,William, Anthony D.,Adsool, Vikrant A.
, p. 1884 - 1887 (2014)
From a medicinal chemistry perspective, bicyclo[1.1.1]pentan-1-amine (1) has served as a unique and important moiety. Synthetically, however, this compound has received little attention, and only one scalable route to this amine has been demonstrated. Reduction of an easily available and potentially versatile intermediate, 1-azido-3-iodobicyclo[1.1.1]pentane (2), can offer both a flexible and scalable alternative to this target. Herein, we describe our scrutiny of this reportedly elusive transformation and report our ensuing success with this endeavor.
Investigation of the Reactivity of 1-Azido-3-iodobicyclo[1.1.1]pentane under click Reaction Conditions
Sitte, Elisabeth,Twamley, Brendan,Grover, Nitika,Senge, Mathias O.
, p. 1238 - 1245 (2021)
The bicyclo[1.1.1]pentane (BCP) unit is under scrutiny as a bioisostere in drug molecules. We employed methodologies for the synthesis of different BCP triazole building blocks from one precursor, 1-azido-3-iodobicyclo[1.1.1]pentane, by click reactions and integrated cycloaddition-Sonogashira coupling reactions. Thereby, we accessed 1,4-disubstituted triazoles, 5-iodo-1,4,5-trisubstituted triazoles, and 5-alkynylated 1,4,5-trisubstituted triazoles. This gives entry to the synthesis of multiply substituted BCP triazoles on either a modular or a one-pot basis. These methodologies were further utilized for appending porphyrin moieties onto the BCP core.
