D. S. Ivanov, M. V. Molchanova, A. Yu. Smirnov, A. A. Mikhaylov, P. N. Solyev, M. S. Baranov, “Synthesis of 3-imino-1-benzazepines by the cyanide-incorporating heterocyclization of (2-benzylaminobenzylidene)malonates”, Mendeleev Commun., 2025, Volume 35, Issue 6,Pages <nobr>639

Communications

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

D. S. Ivanov^a, M. V. Molchanova^a, A. Yu. Smirnov^ab, A. A. Mikhaylov^ab, P. N. Solyev^c, M. S. Baranov^ab

^a M. M. Shemyakin–Yu. A. Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 117997 Moscow, Russian Federation
^b N. I. Pirogov Russian National Research Medical University, 117997 Moscow, Russian Federation
^c V. A. Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, 119991 Moscow, Russian Federation

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.

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

Received: 18.04.2025
Accepted: 29.05.2025

Language: English

DOI: 10.71267/mencom.7805

	*Supplementary materials:*
		Supplementary_data_1.pdf	4.4 Mb