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Hydroxylamine as an ammonia equivalent: access to NH-tetrahydroisoquinolonic derivatives from aldoximes by the Castagnoli–Cushman reaction followed by reduction

Anton Victorovich Bannykh 1
Anton Victorovich Bannykh
, 
Olga Yurievna Bakulina 1
Olga Yurievna Bakulina
, 
Dmitry Viktorovich Dar’in 1
Dmitry Viktorovich Dar’in
, 
Mikhail Yur'evich Krasavin 1
Mikhail Yur'evich Krasavin
10.1016/j.mencom.2019.05.033
Published 2019-04-26
Communication , Volume 29, Issue 3, 337-338
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Bannykh A. V. et al. Hydroxylamine as an ammonia equivalent: access to NH-tetrahydroisoquinolonic derivatives from aldoximes by the Castagnoli–Cushman reaction followed by reduction // Mendeleev Communications. 2019. Vol. 29. No. 3. pp. 337-338.
GOST all authors (up to 50) Copy
Bannykh A. V., Bakulina O. Y., Dar’in D. V., Krasavin M. Y. Hydroxylamine as an ammonia equivalent: access to NH-tetrahydroisoquinolonic derivatives from aldoximes by the Castagnoli–Cushman reaction followed by reduction // Mendeleev Communications. 2019. Vol. 29. No. 3. pp. 337-338.
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TY - JOUR
DO - 10.1016/j.mencom.2019.05.033
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.05.033
TI - Hydroxylamine as an ammonia equivalent: access to NH-tetrahydroisoquinolonic derivatives from aldoximes by the Castagnoli–Cushman reaction followed by reduction
T2 - Mendeleev Communications
AU - Bannykh, Anton Victorovich
AU - Bakulina, Olga Yurievna
AU - Dar’in, Dmitry Viktorovich
AU - Krasavin, Mikhail Yur'evich
PY - 2019
DA - 2019/04/26
PB - Mendeleev Communications
SP - 337-338
IS - 3
VL - 29
ER -
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@article{2019_Bannykh,
author = {Anton Victorovich Bannykh and Olga Yurievna Bakulina and Dmitry Viktorovich Dar’in and Mikhail Yur'evich Krasavin},
title = {Hydroxylamine as an ammonia equivalent: access to NH-tetrahydroisoquinolonic derivatives from aldoximes by the Castagnoli–Cushman reaction followed by reduction},
journal = {Mendeleev Communications},
year = {2019},
volume = {29},
publisher = {Mendeleev Communications},
month = {Apr},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.05.033},
number = {3},
pages = {337--338},
doi = {10.1016/j.mencom.2019.05.033}
}
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Bannykh, Anton Victorovich, et al. “Hydroxylamine as an ammonia equivalent: access to NH-tetrahydroisoquinolonic derivatives from aldoximes by the Castagnoli–Cushman reaction followed by reduction.” Mendeleev Communications, vol. 29, no. 3, Apr. 2019, pp. 337-338. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.05.033.

Abstract

A novel synthetic protocol towards trans-NH-tetrahydroisoquinolonic acid esters is based on the Castagnoli–Cushman reaction between aromatic aldehyde oximes and homophthalic anhydride, followed by esterification and TiCl3-promoted reduction. The scope of the method with respect to the aromatic portion (both electron-rich and electron-deficient) is broader compared to the earlier described approaches, which makes it a suitable synthetic strategy for the structure–activity exploration.

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