Unusual intramolecular cyclization of tris(beta-oximinoalkyl)amines. the first synthesis of 1,4,6,10-tetraazaadamantanes.
An unusual intramolecular cyclization of tris(beta-oximinoalkyl)amines 1 into 4,6,10-trihydroxy-1,4,6,10-tetraazaadamantanes 2 was discovered. Compounds 2 are related to a previously unknown type of heteroadamantanes that contain the cage isomeric to urotropin. A simple three-step synthesis of tetraazaadamantanes 2 and their N-substituted derivatives 3 and 4 from ammonia and aliphatic nitro compounds via the intermediacy of available tris-oximes 1 was developed.
Semakin
Artem N
AN
Higher Chemical College of Russian Academy of Sciences,125047, Miusskaya str., 9, Moscow, Russian Federation.
Sukhorukov
Alexey Yu
AY
Lesiv
Alexey V
AV
Ioffe
Sema L
SL
Lyssenko
Konstantin A
KA
Nelyubina
Yulia V
YV
Tartakovsky
Vladimir A
VA