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A General Synthesis of Bis( o ‐azaheteroaryl)methane Derivatives from N ‐Oxides of Azines and Azoles
Author(s) -
Szpunar Magdalena,
Loska Rafał
Publication year - 2015
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.201500072
Subject(s) - chemistry , isoquinoline , quinoline , cycloaddition , substituent , imidazole , medicinal chemistry , combinatorial chemistry , organic chemistry , catalysis
A general method of preparation of derivatives of bis( o ‐azaheteroaryl)methanes from aromatic N ‐oxides is reported, the key step of which is a 1,3‐dipolar cycloaddition between N ‐oxides of azines or azoles and in situ generated terminal difluoroalkenes containing an o ‐azaheteroaryl substituent at the double bond. Selected products were applied for the preparation of two novel unsymmetrical analogues of BODIPY fluorescent dyes, containing both an imidazole and a quinoline or isoquinoline unit.