A Synthetic Route to Hexahydroimidazoquinolines via Ring-Opening Cyclization of Aziridines with Tetrahydroquinoline
An efficient synthetic route to 1,2,3,3a,4,5-hexahydroimidazo[1,2-<i>a</i>] quinolines in up to 70% yields with high stereoselectivity (<i>dr</i> up to 89:11) via Lewis acid-catalyzed S<sub>N</sub>2-type ring opening of activated aziridines with tetrahydroquinoline, followed by an intramolecular cyclization (ring-opening cyclization, ROC) in the presence of diethyl azo-dicarboxylate (DEAD) as an oxidant has been developed.
Authors
- Manas K. Ghorai (ORCID: https://orcid.org/0000-0002-0472-4757)
- Vashundhra Sharma (ORCID: https://orcid.org/0009-0001-1867-0139)
- Amit Kumar Sharma (ORCID: https://orcid.org/0000-0001-5255-5452)
- Poulami Mandal (ORCID: https://orcid.org/0000-0001-8903-7907)
- S. P. YADAV
Institutions
- Indian Institute of Technology Kanpur (IN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-11-07
- DOI
- https://doi.org/10.1021/acs.joc.5c02155
- Citations
- 1
- Primary Topic
- Synthesis and Catalytic Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.94