Premium
Synthesis of Symmetrical Dinitro‐ and Diamino‐Substituted Tröger's Base Analogues
Author(s) -
Šturala Jiří,
Cibulka Radek
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201188
Subject(s) - nitration , chemistry , amination , regioselectivity , nitro , diamine , base (topology) , stereochemistry , derivative (finance) , reductive amination , nitro compound , halogen , medicinal chemistry , organic chemistry , catalysis , mathematical analysis , alkyl , mathematics , financial economics , economics
This report describes a new synthetic approach to symmetrical diamino‐substituted Tröger's base analogues, allowing the synthesis of 1,7‐, and 4,10‐diamino derivatives with no additional substituents and of 3,9‐diamino derivative with methyl groups in the 1‐, 4‐, 7‐ and 10‐positions. The synthesis uses regioselective nitration of dihalo‐substituted‐ or tetrahalo‐substituted Tröger's bases followed either by hydrogenation of the nitro functions accompanied by removal of halogen atoms or alternatively by chemoselective reduction of nitro groups to obtain the dihalo‐diamino‐substituted Tröger's base analogues. The 2,8‐diamino derivatives, not accessible by this approach, can be prepared by Buchwald–Hartwig amination of the 2,8‐dibromo‐substituted Tröger's bases.