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Linear and cyclic N-acetyl-α-aryl-glycines: Synthesis and chemiluminescence studies

Lineare und cyclische N-Acetyl-α-aryl-glycine: Synthese und Chemilumineszenz-Untersuchungen

  • Organische Chemie Und Biochemie
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Summary

A series of N-acetyl-α-arylglycines (IIa,IIb) was prepared by acid-induced electrophilic α-amidoalkylation reactions; compounds of typeIIb were transformed into the corresponding 3-acetylaminobenzo[b]furan-2(3H)ones (III) by treatment with acetic anhydride. It was found that most of these new compounds (lactones as well as open chain derivatives) undergo base induced oxidation in the presence of oxygen with the emission of visible light. Preliminary structure-activity relationships for these novel chemiluminescence class are proposed.

Zusammenfassung

Eine Reihe von N-Acetyl-α-arylglycinen (IIa,IIb) konnte durch sauer induzierte elektrophile α-Amidoalkylierung hergestellt werden; die Behandlung von Verbindungen des TypsIIb mit Acetanhydrid führte zu den entsprechenden 3-Acetylaminobenzo[b]furan-2(3H)onen (III). Es zeigt sich, daß die Mehrzahl dieser neuen Verbindungen (sowohl Lactone als auch offenkettige Derivate) bei basisch induzierter Oxidation mit (Luft-)Sauerstoff sichtbares Licht emittieren. Erste Struktur-Aktivitäts-Beziehungen für diese neue chemilumineszenzierende Klasse werden vorgeschlagen.

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Authors and Affiliations

  1. Institute of Pharmaceutical Chemistry, University of Innsbruck, A-6020, Innsbruck, Austria

    B. Matuszczak

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  1. B. Matuszczak
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Matuszczak, B. Linear and cyclic N-acetyl-α-aryl-glycines: Synthesis and chemiluminescence studies. Monatsh Chem 127, 1291–1303 (1996). https://doi.org/10.1007/BF00807797

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  • DOI: https://doi.org/10.1007/BF00807797

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