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Synthesis of 3-imino-1-benzazepines by the cyanide-incorporating heterocyclization of (2-benzylaminobenzylidene)malonates

Dmitrii S Ivanov 1
Dmitrii S Ivanov
, 
Marina V Molchanova 1
Marina V Molchanova
, 
Alexander Yuryevich Smirnov 1, 2
Alexander Yuryevich Smirnov
, 
Andrey Andreevich Mikhaylov 1, 2
Andrey Andreevich Mikhaylov
, 
Pavel Nikolaevich Solyev 3
Pavel Nikolaevich Solyev
, 
Mikhail S. Baranov 1, 2
Mikhail S. Baranov
10.71267/mencom.7805
Published 2025-10-21
Communication , Volume 35, Issue 6, 639-641
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Ivanov D. S. et al. Synthesis of 3-imino-1-benzazepines by the cyanide-incorporating heterocyclization of (2-benzylaminobenzylidene)malonates // Mendeleev Communications. 2025. Vol. 35. No. 6. pp. 639-641.
GOST all authors (up to 50) Copy
Ivanov D. S., Molchanova M. V., Smirnov A. Y., Mikhaylov A. A., Solyev P. N., Baranov M. S. Synthesis of 3-imino-1-benzazepines by the cyanide-incorporating heterocyclization of (2-benzylaminobenzylidene)malonates // Mendeleev Communications. 2025. Vol. 35. No. 6. pp. 639-641.
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TY - JOUR
DO - 10.71267/mencom.7805
UR - https://mendcomm.colab.ws/publications/10.71267/mencom.7805
TI - Synthesis of 3-imino-1-benzazepines by the cyanide-incorporating heterocyclization of (2-benzylaminobenzylidene)malonates
T2 - Mendeleev Communications
AU - Ivanov, Dmitrii S
AU - Molchanova, Marina V
AU - Smirnov, Alexander Yuryevich
AU - Mikhaylov, Andrey Andreevich
AU - Solyev, Pavel Nikolaevich
AU - Baranov, Mikhail S.
PY - 2025
DA - 2025/10/21
PB - Mendeleev Communications
SP - 639-641
IS - 6
VL - 35
ER -
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@article{2025_Ivanov,
author = {Dmitrii S Ivanov and Marina V Molchanova and Alexander Yuryevich Smirnov and Andrey Andreevich Mikhaylov and Pavel Nikolaevich Solyev and Mikhail S. Baranov},
title = {Synthesis of 3-imino-1-benzazepines by the cyanide-incorporating heterocyclization of (2-benzylaminobenzylidene)malonates},
journal = {Mendeleev Communications},
year = {2025},
volume = {35},
publisher = {Mendeleev Communications},
month = {Oct},
url = {https://mendcomm.colab.ws/publications/10.71267/mencom.7805},
number = {6},
pages = {639--641},
doi = {10.71267/mencom.7805}
}
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Ivanov, Dmitrii S., et al. “Synthesis of 3-imino-1-benzazepines by the cyanide-incorporating heterocyclization of (2-benzylaminobenzylidene)malonates.” Mendeleev Communications, vol. 35, no. 6, Oct. 2025, pp. 639-641. https://mendcomm.colab.ws/publications/10.71267/mencom.7805.

Keywords

(benzylidene)malonates
1
1-benzazepines
5-hydride shift
cyanide ion
heterocyclization.
tert-amino effect

Abstract

A method for the synthesis of 1,2,3,5-tetrahydro-4H-1-benzazepine-4,4-dicarboxylates from 2-[2-(N-benzyl-N-methylamino)benzylidene]malonates and trimethylsilyl cyanide is proposed. The transformation can be considered as the 1,5-hydride shift-cyclization cascade sequence involving the formation of intermediate stable boronate complex.

Funders

Russian Science Foundation
20-73-10195