Lewis Acid-Catalyzed Cascade Ring Expansion and Intramolecular Friedel–Crafts Type Cyclization of α-Dithioacetyl Propargyl Alcohols: Access to <i>S</i> , <i>S</i> -Heterocycle-Fused Benzofulvenes and 3-Benzylidene-1-indanones
High Resolution Image Download MS PowerPoint Slide The Lewis acid-catalyzed reaction of α-dithioacetyl propargyl alcohols has been reported. This cascade reaction involves the expansion of the dithioacetal ring, followed by a Friedel–Crafts cyclization of the resulting vinylic carbocation intermediates, efficiently producing six-, seven-, and eight-membered S, S -heterocycle-fused benzofulvenes in good yields (up to 98%) within short reaction times (5–40 min). When performed in the presence of water, the same reaction sequence afforded 3-benzylidene-1-indanone derivatives as single E isomers, albeit in lower yields (19–57%)
Authors
- Baris Yücel (ORCID: https://orcid.org/0000-0002-4785-4113)
- Kerem Kaya (ORCID: https://orcid.org/0000-0002-5736-488X)
- Hamdiye Ece (ORCID: https://orcid.org/0000-0002-1782-2022)
- Melda Tayanc
- Mehmet Aytug Sinmaz
- Yigit Efe Turhan
- Bilal Yenidogan
- Rimanur Malikoglu
- Dondu Karademir
- Hüseyin Furkan Ürker (ORCID: https://orcid.org/0009-0000-4838-104X)
- Ikbal Cal (ORCID: https://orcid.org/0009-0000-6060-6707)
Institutions
- Istanbul Technical University (TR)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2026-07-01
- DOI
- https://doi.org/10.1021/acs.joc.6c00685
- Primary Topic
- Synthesis of heterocyclic compounds
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- University of Pennsylvania
- Türkiye Bilimsel ve Teknolojik Araştırma Kurumu
- Istanbul Teknik Üniversitesi
- Bilimsel Araştırma Projeleri Birimi, İstanbul Teknik Üniversitesi