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Lanthanide(III) ion catalyzed reaction of ammonia and nitriles: Synthesis of 2,4,6‐trisubstituted‐ s ‐triazines
Author(s) -
Forsberg John H.,
Spaziano Vincent T.,
Klump Stephen P.,
Sanders Kathleen M.
Publication year - 1988
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.5570250312
Subject(s) - chemistry , propionitrile , acetonitrile , nitrile , yield (engineering) , ammonia , catalysis , alkylation , organic chemistry , lanthanum , medicinal chemistry , materials science , metallurgy
Lanthanum and yttrium trifluoromethanesulfonates at 1 mole % concentration, have been found to catalyze a reaction between ammonia and aromatic nitriles to yield symmetrically substituted 2,4,6‐triaryl‐ s ‐triazines. The generally high yields and relatively mild reaction conditions of this procedure suggest it as an alternative to other aromatic nitrile cyclotrimerization reactions. Of the aliphatic nitriles studied, acetonitrile and cyclopropanecarbonitrile gave good yields of triazine, propionitrile and butyronitrile gave significantly reduced yields of triazines 3b and 3c respectively. Rearrangement of 3a and 3b to alkylated‐4‐aminopyrimidines was observed.