Unusual Intramolecular Cyclization of Tris(β-oximinoalkyl)amines. The First Synthesis of 1,4,6,10-Tetraazaadamantanes

Unusual Intramolecular Cyclization of Tris(β-oximinoalkyl)amines. The First Synthesis of 1,4,6,10-Tetraazaadamantanes Full article

Journal

Organic Letters
ISSN: 1523-7060 , E-ISSN: 1523-7052

Output data

Year: 2009, Volume: 11, Number: 18, Pages: 4072-4075 Pages count : 4 DOI: 10.1021/ol9015157

Authors

Semakin Artem N. ¹ , Sukhorukov Alexey Yu. ² , Lesiv Alexey V. ² , Ioffe Sema L. ² , Lyssenko Konstantin A. ³ , Nelyubina Yulia V. ³ , Tartakovsky Vladimir A. ²

Affiliations

1	Higher Chemical College of Russian Academy of Sciences,125047, Miusskaya str., 9, Moscow, Russian Federation
2	N.D. Zelinsky Institute of Organic Chemistry, 119991, Leninsky prosp. 47, Moscow, Russian Federation,
3	A.N. Nesmeyanov Institute of Organomelement Compounds, Vavilov Str., 28, 119991, Moscow, Russian Federation

An unusual intramolecular cyclization of tris(β-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 A.N. , Sukhorukov A.Y. , Lesiv A.V. , Ioffe S.L. , Lyssenko K.A. , Nelyubina Y.V. , Tartakovsky V.A.
Unusual Intramolecular Cyclization of Tris(β-oximinoalkyl)amines. The First Synthesis of 1,4,6,10-Tetraazaadamantanes
Organic Letters. 2009. V.11. N18. P.4072-4075. DOI: 10.1021/ol9015157 WOS Scopus OpenAlex

Web of science:	WOS:000269670700012
Scopus:	2-s2.0-70349111494
OpenAlex:	W2030965175

DB	Citing
OpenAlex	24
Scopus	27
Web of science	27