Synlett 2016; 27(18): 2561-2566
DOI: 10.1055/s-0035-1562621
letter
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 4,4′-Disubstituted and Spiro-tetrahydroquinolines via Photochemical Cyclization of Acrylanilides and the First Synthesis of (±)-trans-Vabicaserin

Hannes F. Koolman*
a   AbbVie, Discovery Chemistry and Technology, 1 North Waukegan Road, North Chicago, IL 60064, USA   eMail: hannes.koolman@abbvie.com
,
Wilfried M. Braje
b   AbbVie Deutschland GmbH & Co. KG, Neuroscience Discovery Research, Knollstrasse, 67061 Ludwigshafen, Germany
,
Andreas Haupt
b   AbbVie Deutschland GmbH & Co. KG, Neuroscience Discovery Research, Knollstrasse, 67061 Ludwigshafen, Germany
› Institutsangaben
Weitere Informationen

Publikationsverlauf

Received: 17. Juni 2016

Accepted after revision: 28. Juli 2016

Publikationsdatum:
16. August 2016 (online)


Abstract

The synthesis of vabicaserin analogues bearing a quaternary center or spiro substitution at the 4-position has been studied via a [6π]-acrylanilide cyclization employing flow photochemistry in a mesoscale and microfluidic flow photoreactor. The method is also used to synthesize 4,4′-disubstituted tetrahydroquinolines and, furthermore, enables the first synthesis of (±)-trans-vabicaserin.

Supporting Information

 
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