Efficient synthesis of 8-substituted pyrazolo[1,5-a]-1,3,5-triazines by regioselective acylation
1
Laboratoire de Pharmacochimie de la Communication Cellulaire (CNRS, UMR 7081), Faculté de Pharmacie, 74 route du Rhin, BP24, 67401 Illkirch Cedex, France
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2
Laboratoire de Pharmacologie et de Physico-Chimie des Interactions Cellulaires et Moléculaires (CNRS, UMR 7034), Faculté de Pharmacie, 74 route du Rhin, BP24, 67401 Illkirch Cedex, France
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Publication type: Journal Article
Publication date: 2002-12-01
scimago Q3
wos Q3
SJR: 0.334
CiteScore: 3.2
Impact factor: 1.5
ISSN: 00404039, 18733581
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
An efficient two-step synthesis of 8-acylated pyrazolo[1,5- a ]-1,3,5-triazines has been accomplished. The key strategic elements of this novel synthetic approach involve the use of the N -methyl- N -phenylamino activating group, which was easily obtained in high yield by treatment of the pyrazolotriazin-4-one with phosphorus oxychloride and dimethylaniline through high pressure reaction coupled with a regioselective acylation at position 8 followed by the subsequent displacement of the N -methyl- N -phenylamino group upon treatment with various amines.
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Raboisson P. et al. Efficient synthesis of 8-substituted pyrazolo[1,5-a]-1,3,5-triazines by regioselective acylation // Tetrahedron Letters. 2002. Vol. 43. No. 52. pp. 9501-9503.
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Raboisson P., Schultz D., Lugnier C., Bourguignon J. Efficient synthesis of 8-substituted pyrazolo[1,5-a]-1,3,5-triazines by regioselective acylation // Tetrahedron Letters. 2002. Vol. 43. No. 52. pp. 9501-9503.
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TY - JOUR
DO - 10.1016/s0040-4039(02)02456-5
UR - https://doi.org/10.1016/s0040-4039(02)02456-5
TI - Efficient synthesis of 8-substituted pyrazolo[1,5-a]-1,3,5-triazines by regioselective acylation
T2 - Tetrahedron Letters
AU - Raboisson, Pierre
AU - Schultz, Dominique
AU - Lugnier, Claire
AU - Bourguignon, Jean-Jacques
PY - 2002
DA - 2002/12/01
PB - Elsevier
SP - 9501-9503
IS - 52
VL - 43
SN - 0040-4039
SN - 1873-3581
ER -
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BibTex (up to 50 authors)
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@article{2002_Raboisson,
author = {Pierre Raboisson and Dominique Schultz and Claire Lugnier and Jean-Jacques Bourguignon},
title = {Efficient synthesis of 8-substituted pyrazolo[1,5-a]-1,3,5-triazines by regioselective acylation},
journal = {Tetrahedron Letters},
year = {2002},
volume = {43},
publisher = {Elsevier},
month = {dec},
url = {https://doi.org/10.1016/s0040-4039(02)02456-5},
number = {52},
pages = {9501--9503},
doi = {10.1016/s0040-4039(02)02456-5}
}
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MLA
Copy
Raboisson, Pierre, et al. “Efficient synthesis of 8-substituted pyrazolo[1,5-a]-1,3,5-triazines by regioselective acylation.” Tetrahedron Letters, vol. 43, no. 52, Dec. 2002, pp. 9501-9503. https://doi.org/10.1016/s0040-4039(02)02456-5.