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Synthesis of Tetrahydroazepines through Silyl Aza-Prins Cyclization Mediated by Iron(III) Salts

Victoria Sinka*, Israel Fernández and Juan I. Padrón*

*Instituto de Productos Naturales y Agrobiología (IPNA), CSIC, 38206, Avda. Astrofísico Fco. Sánchez 3, 38206 La Laguna, Tenerife (Spain), Email:

V. Sinka, I. Fernández, J. I. Padrón, J. Org. Chem., 2022, 87, 11735-11742.

DOI: 10.1021/acs.joc.2c01396

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A powerful aza-Prins cyclization in combination with the Peterson-type elimination reaction provides seven-membered unsaturated azacycles (tetrahydroazepines) under mild reaction conditions and using iron(III) salts as sustainable catalysts. In a single reaction step, a C-N, C-C bond and an endocyclic double bond are formed.

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proposed mechanism

Key Words

Prins reaction, cyclic amines, N-heterocycles

ID: J42-Y2022