Premium
On the reaction of 5‐aminopyrimidine with diazonium salts
Author(s) -
Swistun Zofia,
Van Der Plas Henk C.
Publication year - 1981
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.5570180832
Subject(s) - triazene , chemistry , substituent , aryl , chloride , salt (chemistry) , derivative (finance) , diazonium compounds , medicinal chemistry , organic chemistry , alkyl , financial economics , economics
The reaction of 5‐aminopyrimidine with benzenediazonium chloride, p ‐methylbenzenediazonium chloride and p ‐bromobenzenediazonium chloride is described. The reaction leads to a mixture of compounds, i.e . 1‐aryl‐3‐(pyrimidin‐5‐yl)triazene ( 6 ), 5‐amino‐4‐aryl‐6‐arylazopyrimidine ( 7 ) and 4‐aryl‐6‐arylazo‐5‐hydroxypyrimidine ( 8 ). The yields are found to be strongly dependent on the substituent present in the diazonium salt. Attempts to rearrange 1‐( p ‐bromophenyl)‐3‐(pyrimidin‐5‐yl)triazene ( 6c ) under basic and acidic conditions into a 1,2,3‐triazole derivative failed.