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Synthesis of 1,2,3,4‐Tetrahydroisoquinolines by Microreactor‐Mediated Thermal Isomerization of Laterally Lithiated Arylaziridines
Author(s) -
Giovine Arianna,
Musio Biagia,
Degennaro Leonardo,
Falcicchio Aurelia,
Nagaki Aiichiro,
Yoshida Junichi,
Luisi Renzo
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201203533
Subject(s) - microreactor , isomerization , aziridine , thermal , chemistry , flow chemistry , tetrahydroisoquinoline , combinatorial chemistry , materials science , photochemistry , organic chemistry , thermodynamics , catalysis , physics , ring (chemistry)
Flow chemistry : A flow‐microreactor‐mediated synthesis of 1,2,3,4‐tetrahydroisoquinolines (THIQs) is reported (see scheme). Starting from a laterally lithiated aziridine, a tetrahydroisoquinoline lithiated at C4 was generated by thermally induced isomerization. Because the reaction temperature is a crucial parameter, the exquisite thermal control possible in a flow‐microreactor system allowed for fast, efficient, and highly reproducible synthesis of functionalized aziridines or THIQs.