79536-75-7Relevant articles and documents
Investigations on Diazo Compounds and Azides, LII: Stable Azomethine Imine Dipoles from Diazo Compounds and 3H-1,2,4-Triazole-3,5(4H)-diones
Theis, Wolfgang,Bethaeuser, Willi,Regitz, Manfred
, p. 28 - 41 (2007/10/02)
The aryl-substituted diazo compounds 1a-h react with the triazolediones 2a-c at 20 deg C in benzene with loss of nitrogen to the stable azomethine imine dipoles 4a-p.Their 1,3-dipolar character is revealed in the addition of methanol and ethanol (4d-f -> 5a-f) as well as in cycloaddition reactions with dimethyl acetylenedicarboxylate (4d,e -> 6a,b) and phenyl isocyanate (4d -> 7).Bisdipoles are obtained by two different ways: Either bisdiazo compounds are reacted with 4-phenyl-3H-1,2,4-triazole-3,5(4H)-dione (12a,b + 2 2a -> 13a,b) or the bistriazoledione 14 is transformed into the bisdipoles 15a-d with diazo compounds (1a,c,d, and i).Dipole moments, molecular weights, IR, UV, 1H NMR, and 13C NMR spectroscopic data are in agreement with the dipole structures.
AZOMETHINE IMINES BASED ON 4-PHENYL-1,2,4-TRIAZOLINE-3,5-DIONE AND ARYL-SUBSTITUTED DIAZOMETHANES
Rodina, L.L.,Lorkina, A.V.,Korobitsyna, I.K.
, p. 1743 - 1749 (2007/10/02)
Stable azomethine imines were obtained from aryl-substituted aliphatic diazo compounds and 4-phenyl-1,2,4-triazoline-3,5-dione.Their properties and their cycloaddition to dimethyl acetylenedicarboxylate, in particular, were investigated.
OBER DIE REAKTIVITAET VON 4-PHENYL-1,2,4-TRIAZOLIN-3,5-DION MIT DIAZOVERBINDUNGEN
Bethaeuser, Willi,Regitz, Manfred,Theis, Wolfgang
, p. 2535 - 2538 (2007/10/02)
The aryl substituted diazo compounds 1a-e react with the triazolindione 2 under the evolution of nitrogen and the formation of the stable dipoles 4a-e.The dipoles resulting from the reaction of 1f-k with 2 cannot be isolated (4f-k) but trapped with ethanol (5f-k).Diazo compounds possessing a butadiene unit (7a-d and 10) prefer Diels-Alder-reaction with 2 and yield the polycycles 9a-d and 11.