Spirocyclic Hybrids of Nortropane and 1,3-Oxazinan-2-one Fragments.

Autor: Mandzhulo, Alexandr, Vashchenko, Iryna, Lukin, Oleg, Shishkina, Svetlana, Dolgonos, Grygoriy, Gerasov, Andrii, Yepishev, Vitaliy, Samofalova, Dariia, Fetyukhin, Volodymyr, Shivanyuk, Alexander
Předmět:
Zdroj: Synthesis; Sep2024, Vol. 56 Issue 17, p2709-2730, 22p
Abstrakt: We report facile and versatile procedures for the synthesis of exo - and endo -isomeric spirocyclic hybrids of pharmacophoric (1 R ,5 S)-8-azabicyclo[3.2.1]octane (nortropane) and 1,3-oxazinan-2-one fragments. Our approach consists of the hydrocyanation of endo - and exo -isomeric N -Cbz-protected nortropane-3-spiroepoxides, the reduction of hydroxy nitriles into amino alcohols, the synthesis of N -alkylated amino alcohols via reductive amination, the spirocyclization of the amino alcohols, N -alkylation of the unsubstituted 1,3-oxazinan-2-one fragment in the spiro compounds, and removal of the Cbz protecting groups. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index