Investigation of reactions of CH-acids with generated in situ N-[1,2-bis(methoxycarbonyl)vinyl]pyridinium in the synthesis of 1,2,3,4,5,6,7-hepta(methoxycarbonyl)cycloheptatriene
Publication type: Journal Article
Publication date: 2024-05-01
scimago Q3
SJR: 0.305
CiteScore: 2.8
Impact factor: —
ISSN: 10665285, 15739171
Abstract
The study investigated the reactivity of various CH-acids/conjugated bases in the synthesis of hepta(methoxycarbonyl)cycloheptatriene through a cascade reaction. NMR spectral monitoring identified (methoxycarbonyl)methylpyridinium as the true nucleophilic component in the original synthesis based on methyl diazoacetate. The scope of CH-acids capable of participating in the reaction was expanded to include sulfonium salts and sulfones, whereas certain nucleophiles were found to be ineffective. A correlation between the pKa values of CH-acids and the formation of seven-membered rings in the cascade reaction was established.
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Citations from 2024:
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Belyy A. Yu. et al. Investigation of reactions of CH-acids with generated in situ N-[1,2-bis(methoxycarbonyl)vinyl]pyridinium in the synthesis of 1,2,3,4,5,6,7-hepta(methoxycarbonyl)cycloheptatriene // Russian Chemical Bulletin. 2024. Vol. 73. No. 5. pp. 1455-1459.
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Belyy A. Yu., Sokolova A. D., Salikov R. F., Platonov D. N., Tomilov Yu. V. Investigation of reactions of CH-acids with generated in situ N-[1,2-bis(methoxycarbonyl)vinyl]pyridinium in the synthesis of 1,2,3,4,5,6,7-hepta(methoxycarbonyl)cycloheptatriene // Russian Chemical Bulletin. 2024. Vol. 73. No. 5. pp. 1455-1459.
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TY - JOUR
DO - 10.1007/s11172-024-4265-z
UR - https://link.springer.com/10.1007/s11172-024-4265-z
TI - Investigation of reactions of CH-acids with generated in situ N-[1,2-bis(methoxycarbonyl)vinyl]pyridinium in the synthesis of 1,2,3,4,5,6,7-hepta(methoxycarbonyl)cycloheptatriene
T2 - Russian Chemical Bulletin
AU - Belyy, A Yu
AU - Sokolova, A D
AU - Salikov, R F
AU - Platonov, D N
AU - Tomilov, Yu V
PY - 2024
DA - 2024/05/01
PB - Springer Nature
SP - 1455-1459
IS - 5
VL - 73
SN - 1066-5285
SN - 1573-9171
ER -
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@article{2024_Belyy,
author = {A Yu Belyy and A D Sokolova and R F Salikov and D N Platonov and Yu V Tomilov},
title = {Investigation of reactions of CH-acids with generated in situ N-[1,2-bis(methoxycarbonyl)vinyl]pyridinium in the synthesis of 1,2,3,4,5,6,7-hepta(methoxycarbonyl)cycloheptatriene},
journal = {Russian Chemical Bulletin},
year = {2024},
volume = {73},
publisher = {Springer Nature},
month = {may},
url = {https://link.springer.com/10.1007/s11172-024-4265-z},
number = {5},
pages = {1455--1459},
doi = {10.1007/s11172-024-4265-z}
}
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MLA
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Belyy, A. Yu., et al. “Investigation of reactions of CH-acids with generated in situ N-[1,2-bis(methoxycarbonyl)vinyl]pyridinium in the synthesis of 1,2,3,4,5,6,7-hepta(methoxycarbonyl)cycloheptatriene.” Russian Chemical Bulletin, vol. 73, no. 5, May. 2024, pp. 1455-1459. https://link.springer.com/10.1007/s11172-024-4265-z.
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