A simple one pot synthesis of condensed 1,2,4-triazines by using the tandem aN-SNipsoand SNH-SNipsareactions
O. N. Chupakhin
1
,
Gennady L. Rusinov
1
,
Dmitry G Beresnev
1
,
Valery Charushin
1
,
Hans Neunhoeffer
2
Publication type: Journal Article
Publication date: 2001-07-01
scimago Q3
wos Q2
SJR: 0.362
CiteScore: 4.7
Impact factor: 2.4
ISSN: 0022152X, 19435193
Organic Chemistry
Abstract
A new synthetic approach to condensed 1,2,4-triazines based on using the tandem AN-SNipso and SNH-SNipso reactions has been developed. 5-Methoxy-3-penyl-1,2,4-triazine and its N1-methyl quaternary salt were found to react with C,N-, C,O- and N,N'-bifunctional nucleophiles (m-phenylenediamine, resor-cinol, semicarbazide and ureas) into triazacarbazoles, benzofuro[2,3-e][1,2,4]-triazines, and 6-azapurine derivatives. In all cases nucleophiles attack first the unsubstituted C-6 carbon of the triazine ring, while the final stage is replacement of the methoxy group affording cyclization products.
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Total citations:
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Citations from 2024:
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(5.88%)
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Chupakhin O. N. et al. A simple one pot synthesis of condensed 1,2,4-triazines by using the tandem aN-SNipsoand SNH-SNipsareactions // Journal of Heterocyclic Chemistry. 2001. Vol. 38. No. 4. pp. 901-907.
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Chupakhin O. N., Rusinov G. L., Beresnev D. G., Charushin V., Neunhoeffer H. A simple one pot synthesis of condensed 1,2,4-triazines by using the tandem aN-SNipsoand SNH-SNipsareactions // Journal of Heterocyclic Chemistry. 2001. Vol. 38. No. 4. pp. 901-907.
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RIS
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TY - JOUR
DO - 10.1002/jhet.5570380414
UR - https://doi.org/10.1002/jhet.5570380414
TI - A simple one pot synthesis of condensed 1,2,4-triazines by using the tandem aN-SNipsoand SNH-SNipsareactions
T2 - Journal of Heterocyclic Chemistry
AU - Chupakhin, O. N.
AU - Rusinov, Gennady L.
AU - Beresnev, Dmitry G
AU - Charushin, Valery
AU - Neunhoeffer, Hans
PY - 2001
DA - 2001/07/01
PB - Wiley
SP - 901-907
IS - 4
VL - 38
SN - 0022-152X
SN - 1943-5193
ER -
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BibTex (up to 50 authors)
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@article{2001_Chupakhin,
author = {O. N. Chupakhin and Gennady L. Rusinov and Dmitry G Beresnev and Valery Charushin and Hans Neunhoeffer},
title = {A simple one pot synthesis of condensed 1,2,4-triazines by using the tandem aN-SNipsoand SNH-SNipsareactions},
journal = {Journal of Heterocyclic Chemistry},
year = {2001},
volume = {38},
publisher = {Wiley},
month = {jul},
url = {https://doi.org/10.1002/jhet.5570380414},
number = {4},
pages = {901--907},
doi = {10.1002/jhet.5570380414}
}
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MLA
Copy
Chupakhin, O. N., et al. “A simple one pot synthesis of condensed 1,2,4-triazines by using the tandem aN-SNipsoand SNH-SNipsareactions.” Journal of Heterocyclic Chemistry, vol. 38, no. 4, Jul. 2001, pp. 901-907. https://doi.org/10.1002/jhet.5570380414.