3,4-Dimethoxypyridine-2-carbaldehyde in the synthesis of quinazolin-4(3H)-ones: partial demethylation at the dehydrogenation step
E S Starnovskaya
1
,
A. L. Muzyka
1
,
A. A. Yurtaeva
1
,
A E Kopotilova
1
,
D S Kopchuk
1, 2
,
V S Gaviko
1, 3
,
O S Taniya
1
,
E.V Nosova
1, 2
,
G V Zyryanov
1, 2
,
V L Rusinov
1, 2
Publication type: Journal Article
Publication date: 2025-02-01
scimago Q3
SJR: 0.305
CiteScore: 2.8
Impact factor: —
ISSN: 10665285, 15739171
Abstract
The cyclocondensation of 2-aminobenzamide with 3,4-dimethoxypyridine-2-carbaldehyde affords a mixture of 2-(3,4-dimethoxypyridin-2-yl)-2,3-dihydroquinazolin-4(1H)-one and its open-chain tautomer. The dehydrogenation of these compounds with benzoquinones (DDQ, chloranil) as oxidants, giving 2-(pyridin-2-yl)quinazolin-4(3H)-ones, is accompanied by the demethylation of the methoxy group at the C(3) position of the 2-pyridyl moiety. When using 2-methoxy- or 2,3,4-trimethoxybenzaldehydes as deaza analogs of this aldehyde, the demethylation does not occur in the last step regardless of the nature of the oxidant.
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Starnovskaya E. S. et al. 3,4-Dimethoxypyridine-2-carbaldehyde in the synthesis of quinazolin-4(3H)-ones: partial demethylation at the dehydrogenation step // Russian Chemical Bulletin. 2025. Vol. 74. No. 2. pp. 483-488.
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Starnovskaya E. S., Muzyka A. L., Yurtaeva A. A., Kopotilova A. E., Kopchuk D. S., Gaviko V. S., Taniya O. S., Nosova E., Zyryanov G. V., Rusinov V. L. 3,4-Dimethoxypyridine-2-carbaldehyde in the synthesis of quinazolin-4(3H)-ones: partial demethylation at the dehydrogenation step // Russian Chemical Bulletin. 2025. Vol. 74. No. 2. pp. 483-488.
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TY - JOUR
DO - 10.1007/s11172-025-4540-7
UR - https://link.springer.com/10.1007/s11172-025-4540-7
TI - 3,4-Dimethoxypyridine-2-carbaldehyde in the synthesis of quinazolin-4(3H)-ones: partial demethylation at the dehydrogenation step
T2 - Russian Chemical Bulletin
AU - Starnovskaya, E S
AU - Muzyka, A. L.
AU - Yurtaeva, A. A.
AU - Kopotilova, A E
AU - Kopchuk, D S
AU - Gaviko, V S
AU - Taniya, O S
AU - Nosova, E.V
AU - Zyryanov, G V
AU - Rusinov, V L
PY - 2025
DA - 2025/02/01
PB - Springer Nature
SP - 483-488
IS - 2
VL - 74
SN - 1066-5285
SN - 1573-9171
ER -
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@article{2025_Starnovskaya,
author = {E S Starnovskaya and A. L. Muzyka and A. A. Yurtaeva and A E Kopotilova and D S Kopchuk and V S Gaviko and O S Taniya and E.V Nosova and G V Zyryanov and V L Rusinov},
title = {3,4-Dimethoxypyridine-2-carbaldehyde in the synthesis of quinazolin-4(3H)-ones: partial demethylation at the dehydrogenation step},
journal = {Russian Chemical Bulletin},
year = {2025},
volume = {74},
publisher = {Springer Nature},
month = {feb},
url = {https://link.springer.com/10.1007/s11172-025-4540-7},
number = {2},
pages = {483--488},
doi = {10.1007/s11172-025-4540-7}
}
Cite this
MLA
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Starnovskaya, E. S., et al. “3,4-Dimethoxypyridine-2-carbaldehyde in the synthesis of quinazolin-4(3H)-ones: partial demethylation at the dehydrogenation step.” Russian Chemical Bulletin, vol. 74, no. 2, Feb. 2025, pp. 483-488. https://link.springer.com/10.1007/s11172-025-4540-7.