The mechanism of Tröger's base formation probed by electrospray ionization mass spectrometry.
Using direct infusion electrospray ionization mass and tandem mass spectrometric experiments [ESI-MS(/MS)], we have performed on-line monitoring of some reactions used to form Tröger's bases. Key intermediates, either as cationic species or as protonated forms of neutral species, have been intercepted and characterized. The role of urotropine as the methylene source in these reactions has also been accessed. Reaction pathways shown by ESI-MS(/MS) have been probed by gas-phase ion/molecule reactions, and an expanded mechanism for Tröger's base formation based on the mass spectrometric data has been elaborated.
Abella
Carlos A M
CA
Laboratory of Synthesis of Natural Products and Drugs and the ThoMSon Mass Spectrometry Laboratory, Institute of Chemistry, State University of Campinas, UNICAMP, 13084-971 Campinas, SP, Brazil.
Benassi
Mario
M
Santos
Leonardo S
LS
Eberlin
Marcos N
MN
Coelho
Fernando
F
D000814:Aniline Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D001392:Azocines / Q000737:chemistry* / Q000378:metabolism; D002853:Chromatography, Liquid; D005557:Formaldehyde / Q000737:chemistry; D008709:Methenamine / Q000737:chemistry; D008956:Models, Chemical; D008958:Models, Molecular; D015394:Molecular Structure; D021241:Spectrometry, Mass, Electrospray Ionization; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D013930:Thromboxane-A Synthase / Q000037:antagonists & inhibitors
D000814:Aniline Compounds; D001392:Azocines; D005557:Formaldehyde; C083830:Troeger's base; D013930:Thromboxane-A Synthase; D008709:Methenamine; C023650:aniline