TY - JOUR
T1 - Dimethylamino-substituted 7H-benzo[de]pyrazolo[5,1-a]isoquinolin-7-ones and their behavior under Vilsmeier-Haack conditions
AU - Lyubenko, O. N.
AU - Ermolenko, I. G.
AU - Patsenker, L. D.
AU - Krasovitskii, B. M.
AU - Tur, I. N.
N1 - Funding Information:
The authors thank cand. biol. sci. V. I. Musatov (Institute of Monocrystals, Ukraine National Academy of Sciences) for measuring the 1H NMR spectra. The work was carried out with a subvention from the Ukraine National Academy of Sciences, grant No. 0801051062.
PY - 2003/4
Y1 - 2003/4
N2 - The behavior of dimethylamino-substituted 7H-benzo[de]pyrazolo[5,1-a]isoquinoline-7-ones, synthesized for the first time, under conditions of the Vilsmeier-Haack reaction. It has been shown that, on heating with POCl3 and DMF, they are converted by electrophilic substitution at the position ortho to the dimethylamino group, followed by cyclization of the iminium adduct to a quinazolinium salt. When an acetyl group is present, the Arnold reaction, leading to the formation of a chloroaryl, accompanies the heterocyclization. The rates and proportion of the reaction products depend on the position of the dimethyl groups relative to the pyrazole ring.
AB - The behavior of dimethylamino-substituted 7H-benzo[de]pyrazolo[5,1-a]isoquinoline-7-ones, synthesized for the first time, under conditions of the Vilsmeier-Haack reaction. It has been shown that, on heating with POCl3 and DMF, they are converted by electrophilic substitution at the position ortho to the dimethylamino group, followed by cyclization of the iminium adduct to a quinazolinium salt. When an acetyl group is present, the Arnold reaction, leading to the formation of a chloroaryl, accompanies the heterocyclization. The rates and proportion of the reaction products depend on the position of the dimethyl groups relative to the pyrazole ring.
KW - 7H-benzo[de]pyrazolo[5,1-a]isoquinoline-7-ones
KW - Heterocyclization
KW - Quinazolinium salts
KW - The Vilsmeier-Haack reaction
UR - http://www.scopus.com/inward/record.url?scp=0142028039&partnerID=8YFLogxK
U2 - 10.1023/A:1024773632076
DO - 10.1023/A:1024773632076
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AN - SCOPUS:0142028039
SN - 0009-3122
VL - 39
SP - 511
EP - 519
JO - Chemistry of Heterocyclic Compounds
JF - Chemistry of Heterocyclic Compounds
IS - 4
ER -