TY - JOUR
T1 - An activated trifluoromethyl group as a new synthon for 4,5‐dihydro‐1H‐imidazole and 1,4,5,6‐tetrahydropyrimidine systems
AU - Wydra, Roman L.
AU - Patterson, Steven E.
AU - Strekowski, Lucjan
PY - 1990
Y1 - 1990
N2 - Treatment of 4‐(trifluoromethyl)benzenamine 1a and 2‐(trifluoromethyl)benzamine 1b with lithium 2‐aminoethylamide gives 2‐(4‐aminophenyl)‐4,5‐dihydro‐1H‐imidazole 3a and 2‐(2‐aminophenyl)‐4,5‐dihydro‐1H‐imidazole 3b, respectively. Similar reactions of 1a and 1b with lithium 3‐aminopropylamide produce the respective 2‐(aminophenyl)‐1,4,5,6‐tetrahydropyrimidines 4a and 4b. 3‐(Trifluoromethyl)benzenamine 1c is recovered unchanged from analogous mixtures. The mechanism is discussed.
AB - Treatment of 4‐(trifluoromethyl)benzenamine 1a and 2‐(trifluoromethyl)benzamine 1b with lithium 2‐aminoethylamide gives 2‐(4‐aminophenyl)‐4,5‐dihydro‐1H‐imidazole 3a and 2‐(2‐aminophenyl)‐4,5‐dihydro‐1H‐imidazole 3b, respectively. Similar reactions of 1a and 1b with lithium 3‐aminopropylamide produce the respective 2‐(aminophenyl)‐1,4,5,6‐tetrahydropyrimidines 4a and 4b. 3‐(Trifluoromethyl)benzenamine 1c is recovered unchanged from analogous mixtures. The mechanism is discussed.
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U2 - 10.1002/jhet.5570270359
DO - 10.1002/jhet.5570270359
M3 - Letter
AN - SCOPUS:84986461298
SN - 0022-152X
VL - 27
SP - 803
EP - 805
JO - Journal of Heterocyclic Chemistry
JF - Journal of Heterocyclic Chemistry
IS - 3
ER -