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

The synthesis of vabicaserin analogues bearing a quaternary center or spiro substitution at the 4-position has been studied via a [6]-acrylanilide cyclization employing flow photochemistry in a mesoscale and microfluidic flow photoreactor. The method is also used to synthesize 4,4-disubstituted tetr...

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Bibliographic Details
Published inSynlett Vol. 27; no. 18; pp. 2561 - 2566
Main Authors Koolman, Hannes F., Braje, Wilfried M., Haupt, Andreas
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 14.11.2016
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
DIHYDROQUINOLINONES
ASYMMETRIC-SYNTHESIS
ONE-POT SYNTHESIS
vabicaserin
flow photochemistry
electrocyclization
electrocyclic reactions
tetrahydroquinoline
IDENTIFICATION
AGONISTS
photocyclization
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Summary:The synthesis of vabicaserin analogues bearing a quaternary center or spiro substitution at the 4-position has been studied via a [6]-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.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0035-1562621