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Electron Impact Induced Loss of C‐5/C‐8 Substituents of 1,2,3,4‐Tetrahydroisoquinolines, VI 1) : Synthesis and Mass Spectrometric Fragmentation of Dihydroindole Derivatives
Author(s) -
Knefeli Frank,
Mayer Klaus K.,
Wiegrebe W.,
Schlunegger Urs P.,
Lauber Rolf
Publication year - 1990
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.19903230305
Subject(s) - chemistry , fragmentation (computing) , mass spectrum , electron ionization , stereochemistry , medicinal chemistry , mass spectrometry , organic chemistry , ion , chromatography , computer science , ionization , operating system
The syntheses of the C‐4 substituted dihydroindoles 25, 31 (scheme 7), and 36 (scheme 8) are described. ‐ The CID MIKE spectrum in the 2. field free region (2. FFR) of m/z 146 from 25 is very similar to but not identical with that of m/z 146 from the C‐5 substituted tetrahydroisoquinolines 3, 6, 7 , and 8 (scheme 2), so supporting our hypothesis of a rearrangement in M + of tetrahydroisoquinolines 1) prior to fragmentation, but not proving it. As the CID MIKE spectra of the tetrahydroisoquinolines 3, 6, 7 , and 8 are not identical among each other we assume that a 1.3‐H‐shift takes places in their M + in competition to the rearrangement mentioned above.