Facile Synthesis of 5‐Halo‐1,2,3‐Triazole‐Fused Benzotricyclic Frameworks from 1‐(ω‐Azidoalkyl)‐2‐(2,2‐Dihalovinyl)Arenes and their Application in Fluorescent Triazole Derivatives
By heating 1‐(ω‐azidoalkyl)‐2‐(2,2‐dihalovinyl)arenes in DMF, intramolecular Huisgen cycloaddition between the azido group and the 1,1‐dihalovinyl moiety proceeds smoothly to afford 5‐halo‐1,2,3‐triazole‐fused tricyclic benzocondensed compounds. Leveraging the remaining halogen groups, the carbon chain extension via the Mizoroki–Heck or Suzuki–Miyaura coupling reactions, followed by an intramolecular Friedel–Crafts reaction, furnish polycyclic systems that incorporate fused triazole rings. Furthermore, the transformation of the halogen groups into the 2‐nitrobenzene derivatives via Suzuki–Miyaura cross‐coupling, followed by a Cadogan reaction using triphenylphosphine, provides a series of fluorescent pentacyclic compounds.
Authors
- Tadaomi Furuta (ORCID: https://orcid.org/0000-0003-4568-9043)
- Nobuaki Funahashi (ORCID: https://orcid.org/0000-0003-0888-1060)
- Satoru Karasawa
- Hideya Yuasa (ORCID: https://orcid.org/0000-0002-2864-3185)
- Kazushi Kinbara (ORCID: https://orcid.org/0000-0002-5945-9612)
- Takashi Kanamori (ORCID: https://orcid.org/0000-0002-1782-9283)
- Ai Kohata (ORCID: https://orcid.org/0000-0003-2019-559X)
- M. Ebihara
- Shota Matsumoto (ORCID: https://orcid.org/0000-0002-8243-7163)
- Naohiko Koshikawa (ORCID: https://orcid.org/0000-0002-4539-888X)
- Seiya Kikukawa
- Nozomi Kasakura
- Takeshi Hata (ORCID: https://orcid.org/0000-0002-7500-5995)
- Kazuki Kobayashi (ORCID: https://orcid.org/0000-0002-9365-9490)
Institutions
- Tokyo Institute of Technology (JP)
- Showa Pharmaceutical University (JP)
Publication Details
- Journal
- European Journal of Organic Chemistry
- Published
- 2025-06-13
- DOI
- https://doi.org/10.1002/ejoc.202500355
- Primary Topic
- Click Chemistry and Applications
- Type
- article
- Field-Weighted Citation Impact
- 0.00