Preparation and Transformations of Acetophenone-Derived Enamino Ketones, BF2-β-Ketoiminates, and BF2-β-Diketonates
A series of differently substituted β-enaminones <b>2a</b>,<b>b</b>, <b>4a</b>-<b>i</b>, <b>8a</b>-<b>d</b>, and <b>9</b>-<b>13</b>, their BF<sub>2</sub>-β-ketoiminate complexes <b>5a</b>-<b>d</b>, and BF<sub>2</sub>-β-diketonate complexes <b>6a</b>-<b>d</b> were prepared as model substrates for photochemical transformations. The attempted photochemical transformations of enaminones <b>2</b>, <b>4</b>, <b>8</b> and BF<sub>2</sub>-β-ketoiminate complexes <b>5</b> failed. On the other hand, irradiation of mixtures of BF<sub>2</sub>-β-diketonate complexes <b>6a</b>-<b>d</b> and cycloalkanes with UV-A light (365 nm) gave the corresponding De Mayo reaction products <b>7a</b>-<b>f</b> in 9-30% yields. The photochemical ring-expansion of acetyl tetralone-derived BF<sub>2</sub>-complex <b>6d</b> gave novel diannulated cyclooctane derivatives <b>7e</b> and <b>7f</b>, which would be difficult to obtain using conventional cyclization methods.
Authors
- Uroš Grošelj (ORCID: https://orcid.org/0000-0002-5186-9879)
- Bogdan Štefane (ORCID: https://orcid.org/0000-0002-8709-9853)
- Helena Brodnik (ORCID: https://orcid.org/0000-0002-0099-2236)
- Nejc Petek (ORCID: https://orcid.org/0000-0003-3331-4885)
- Jurij Svete (ORCID: https://orcid.org/0000-0003-3339-3595)
- Luka Ciber (ORCID: https://orcid.org/0000-0002-6631-1974)
Institutions
- University of Ljubljana (SI)
Publication Details
- Journal
- Molecules
- Published
- 2025-01-29
- DOI
- https://doi.org/10.3390/molecules30030601
- Primary Topic
- Synthesis and Characterization of Pyrroles
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- American Roentgen Ray Society
- Univerza v Ljubljani