Premium
Synthesis of large macrocyclic tetraaza compounds with a methylene backbone: Cyclo[‐NH‐ (CH 2 ) n ‐] 4 , (n = 6, 7, 8, 9 and 10). The formation of 28‐, 32‐, 36‐, 40‐ and 44‐membered rings
Author(s) -
Tomohiro Takenori,
Uoto Kouichi,
Okuno Hiroaki Yohmei
Publication year - 1990
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570270513
Subject(s) - chemistry , methylene , condensation , condensation reaction , stereochemistry , medicinal chemistry , organic chemistry , thermodynamics , catalysis , physics
A series of macrocyclic tetraamines with 28‐, 32‐, 36‐, 40‐ and 44‐membered rings have been efficiently prepared from the corresponding ditosylamide and monobromoalcohol derivatives in 6 steps via a double condensation reaction. Overall yields were: 41, 41, 46, 29, and 33%, respectively, for 1,8,15,22‐tetraazacyclooctacontane ( 11a ), 1,9,17,25‐tetraazacyclodotriacontane ( 11b ), 1,10,19,28‐tetraazacyclohexatriacontane ( 11c ), 1,11,21,31‐tetraazacyclotetracontane ( 11d ) and 1,12,23,34‐tetraazacyclotetratetracontane ( 11e ).