A Synthetic Route to Tetrahydro-1<i>H</i>-azepino[4,3,2-<i>cd</i>]indoles via Ring-Opening Cyclization of Activated Azetidines with 4-Bromoindole: Toward a Vasopressin V2 Receptor Antagonist
A simple one-pot, two-step strategy for the synthesis of tetrahydro-1<i>H</i>-azepino[4,3,2-<i>cd</i>]indoles via Lewis acid-catalyzed S<sub>N</sub>2-type ring opening of activated azetidines with 4-bromoindole, followed by a Pd-catalyzed intramolecular C-N cyclization reaction, with good to excellent yields is described. Utilizing this protocol, the vasopressin V2 receptor antagonist precursor has been synthesized easily. Enantioenriched tetrahydro-1<i>H</i>-azepino[4,3,2-<i>cd</i>]indoles were obtained by starting from enantiopure azetidine.
Authors
- Manas K. Ghorai (ORCID: https://orcid.org/0000-0002-0472-4757)
- Abhijit Mal (ORCID: https://orcid.org/0000-0002-1829-7661)
- Gaurav Goswami (ORCID: https://orcid.org/0000-0001-8492-2181)
- Imtiyaz Ahmad Wani (ORCID: https://orcid.org/0000-0001-5421-2146)
- Bharat Singh (ORCID: https://orcid.org/0000-0003-2865-5829)
Institutions
- Indian Institute of Technology Kanpur (IN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2024-08-05
- DOI
- https://doi.org/10.1021/acs.joc.4c01270
- Citations
- 15
- Primary Topic
- Synthesis and Catalytic Reactions
- Type
- article
- Field-Weighted Citation Impact
- 3.75
Funders
- Indian Institute of Technology Kanpur
- Science and Engineering Research Board