Synthesis of Phenanthrenes and Naphthoquinone Fused Benzoxepines via Hauser–Kraus Annulation of Sulfonylphthalide with Morita–Baylis–Hillman Adducts of Nitroalkenes
The Hauser-Kraus annulation of sulfonylphthalide with Morita-Baylis-Hillman (MBH) adducts of nitroalkenes provides access to phenanthrenes and naphthoquinone fused dihydrobenzoxepines. The H-K annulation results in naphthoquinones bearing a key alcohol group in protected form, which leads to naphthoquinone fused tetracyclic oxepines upon reaction with formaldehyde. These alcohols yield functionalized phenanthrenes via oxidation and [3 + 3] annulation with β-ketoesters.
Authors
- Shweta Prakash Gaikwad (ORCID: https://orcid.org/0009-0001-7036-4251)
- Irishi N. N. Namboothiri (ORCID: https://orcid.org/0000-0002-8945-3932)
- Thekke V. Baiju
- Chenikkayala Siva Sankara (ORCID: https://orcid.org/0000-0001-5671-3315)
- Rajni Kumari (ORCID: https://orcid.org/0009-0008-3137-786X)
- Suman Das Adhikary (ORCID: https://orcid.org/0000-0002-0570-9794)
Institutions
- Indian Institute of Technology Bombay (IN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-04-15
- DOI
- https://doi.org/10.1021/acs.joc.5c00189
- Primary Topic
- Biological and pharmacological studies of plants
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- University Grants Commission
- Ministry of Education, India
- Indian Institute of Technology Bombay
- Science and Engineering Research Board