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Alkylamination of pteridines by primary alkylamines ‐ potassium permanganate
Author(s) -
Sladowska H.,
Van Veldhuizen A.,
Van Der Plas H. C.
Publication year - 1986
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.5570230336
Subject(s) - ethylamine , chemistry , potassium permanganate , adduct , butylamine , pteridine , propylamine , potassium , derivative (finance) , permanganate , medicinal chemistry , amine gas treating , organic chemistry , financial economics , economics , enzyme
Reaction of 7‐phenyl, 7‐p‐methoxyphenyl, 7‐ t ‐butyl‐ and 6,7‐diphenylpteridine with ethylamine and t ‐butylamine in the presence of potassium permanganate leads to the introduction of the ethylamino or t ‐butylamino group at C‐4 in the above‐mentioned pteridines. In the reaction of ethylamine/potassium permanganate besides the 4‐(ethylamino)pteridine derivatives 2‐amino‐3‐formytpyrazines are obtained as side‐products. In the reaction with t ‐butylamine/potassium permanganate the corresponding pteridin‐4‐ones are obtained as by‐products. The 1 H nmr spectroscopic studies have revealed that at room temperature ethylamine easily gives a σ‐adduct at C‐4, yielding a 4‐(ethylamino)‐3,4‐dihydropteridine derivative. t ‐Butylamine, however, only gives with the pteridines addition at C‐4 at low temperature, i.e . at −40°. This adduct dissociates at room temperature. n ‐Propylamine and n ‐butylamine show the same behavior as ethylamine.