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 | Zendy

Knefeli Frank | Zendy; Mayer Klaus K. | Zendy; Wiegrebe W. | Zendy; Schlunegger Urs P. | Zendy; Lauber Rolf | Zendy

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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.

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