A Synthetic Route to Tetrahydro-1 H -azepino[4,3,2- cd ]indoles via Ring-Opening Cyclization of Activated Azetidines with 4-Bromoindole: Toward a Vasopressin V2 Receptor Antagonist

A Synthetic Route to Tetrahydro-1 H -azepino[4,3,2- cd ]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 -azepino[4,3,2- ]indoles via Lewis acid-catalyzed S 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. Ut...

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Veröffentlicht in:Journal of organic chemistry 2024-08, Vol.89 (16), p.11576-11587
Hauptverfasser: Goswami, Gaurav, Singh, Bharat, Wani, Imtiyaz Ahmad, Mal, Abhijit, Ghorai, Manas K
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container_end_page 11587
container_issue 16
container_start_page 11576
container_title Journal of organic chemistry
container_volume 89
creator Goswami, Gaurav
Singh, Bharat
Wani, Imtiyaz Ahmad
Mal, Abhijit
Ghorai, Manas K
description A simple one-pot, two-step strategy for the synthesis of tetrahydro-1 -azepino[4,3,2- ]indoles via Lewis acid-catalyzed S 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 -azepino[4,3,2- ]indoles were obtained by starting from enantiopure azetidine.
doi_str_mv 10.1021/acs.joc.4c01270
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title A Synthetic Route to Tetrahydro-1 H -azepino[4,3,2- cd ]indoles via Ring-Opening Cyclization of Activated Azetidines with 4-Bromoindole: Toward a Vasopressin V2 Receptor Antagonist
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