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Mannich-type three component condensation of α-substituted caran-4-one oximes with formaldehyde and secondary amines

Nikolaj Borisovich Gorshkov 1
Nikolaj Borisovich Gorshkov
, 
Alexander Mikhailovich Agafontsev 1
Alexander Mikhailovich Agafontsev
, 
Yuriy Vasil'evich Gatilov 1
Yuriy Vasil'evich Gatilov
, 
Alexey Vasil'evich Tkachev 1, 2
Alexey Vasil'evich Tkachev
10.1016/j.mencom.2009.05.008
Published 2009-05-08
Communication , Volume 19, Issue 3, 139-140
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Gorshkov N. B. et al. Mannich-type three component condensation of α-substituted caran-4-one oximes with formaldehyde and secondary amines // Mendeleev Communications. 2009. Vol. 19. No. 3. pp. 139-140.
GOST all authors (up to 50) Copy
Gorshkov N. B., Agafontsev A. M., Gatilov Y. V., Tkachev A. V. Mannich-type three component condensation of α-substituted caran-4-one oximes with formaldehyde and secondary amines // Mendeleev Communications. 2009. Vol. 19. No. 3. pp. 139-140.
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TY - JOUR
DO - 10.1016/j.mencom.2009.05.008
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2009.05.008
TI - Mannich-type three component condensation of α-substituted caran-4-one oximes with formaldehyde and secondary amines
T2 - Mendeleev Communications
AU - Gorshkov, Nikolaj Borisovich
AU - Agafontsev, Alexander Mikhailovich
AU - Gatilov, Yuriy Vasil'evich
AU - Tkachev, Alexey Vasil'evich
PY - 2009
DA - 2009/05/08
PB - Mendeleev Communications
SP - 139-140
IS - 3
VL - 19
ER -
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@article{2009_Gorshkov,
author = {Nikolaj Borisovich Gorshkov and Alexander Mikhailovich Agafontsev and Yuriy Vasil'evich Gatilov and Alexey Vasil'evich Tkachev},
title = {Mannich-type three component condensation of α-substituted caran-4-one oximes with formaldehyde and secondary amines},
journal = {Mendeleev Communications},
year = {2009},
volume = {19},
publisher = {Mendeleev Communications},
month = {May},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2009.05.008},
number = {3},
pages = {139--140},
doi = {10.1016/j.mencom.2009.05.008}
}
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Gorshkov, Nikolaj Borisovich, et al. “Mannich-type three component condensation of α-substituted caran-4-one oximes with formaldehyde and secondary amines.” Mendeleev Communications, vol. 19, no. 3, May. 2009, pp. 139-140. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2009.05.008.

Keywords

alpha-substituted oximes
alpha-thio-oximes
aminomethylation
carene
Mannich reaction
oxime

Abstract

Under the conditions of the Mannich reaction, 3-substituted oximes of caran-4-one undergo aminomethylation at the α-carbon atom to oxime. The reaction takes place successfully only in a mixture of methanol and acetic acid to produce α-aminomethyl derivatives in 25–83% yields. The secondary or tertiary amino group at the α’-position is eliminated under the reaction conditions to form derivatives of α,β-unsaturated oxime, while sulfur-containing substituents remain unchanged.

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