Unexpected Discovery of Saturated Pyridine Mimetics

ChemRxiv 2023, in press

DOI: 10.26434/chemrxiv-2023-jbb0r

Dibchak D.; Snisarenko M.; Mishuk A.; Shablykin O.; Bortnichuk L.; Klymenko-Ulianov O.; Kheylik Y.; Sadkova I.; Rzepa H.; Mykhailiuk P.

A general approach to 3-azabicyclo[3.1.1]heptanes was unexpectedly discovered. The mechanism, scope, and scalability of this method were studied. The core was incorporated into the structure of the antihistamine drug Rupatidine instead of the pyridine ring, which led to a dramatic improvement in physicochemical properties.