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- W2034987525 abstract "Die Propargylazide 10, 14, 17, 20 und 28 lagern sich basenkatalysiert (prototrop) zu kurzlebigen Allenylaziden um. Diese Zwischenstufen cyclisieren rasch zu Triazafulvenen, die mit Nucleophilen (Methanol, Natriumhydroxid, Ammoniak) als 1,2,3-Triazole abgefangen werden können. Ausgehend von den Vorläufern 9, 13, 16, 19 und 27 führen Eintopf-Synthesen zu den Heterocyclen 12, 15, 18, 21 und 29. In Abhängigkeit von den Reaktionsbedingungen liefert 10 über die prototrope Umlagerung (Weg B) regioselektiv 12c (75%) oder durch Azidwanderung (Weg A) die isomere Verbindung 11c (62%). Reactions of Unsaturated Azides, 7. — Base-catalyzed Formation of Allenyl Azides from Propargyl Azides: New Syntheses for 1,2,3-Triazoles The propargyl azides 10, 14, 17, 20, and 28 undergo a base-catalyzed (prototropic) rearrangement to short-lived allenyl azides. These intermediates rapidly cyclize to triazafulvenes, which can be trapped by nucleophiles (methanol, sodium hydroxide, ammonia) to give 1,2,3-triazoles. Starting with the precursors 9, 13, 16, 19, and 27 one-pot syntheses lead to the heterocycles 12, 15, 18, 21, and 29. Depending on the reaction conditions, compound 10 regioselectively yields 12c (75%) by prototropic rearrangement (path B) or by migration of the azide group (path A) the isomer 11c (62%)." @default.
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- W2034987525 date "1989-10-01" @default.
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- W2034987525 title "Reaktionen ungesättigter Azide, 7: Basenkatalysierte Bildung von Allenylaziden aus Propargylaziden: Neue Synthesen für 1,2,3‐Triazole" @default.
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- W2034987525 doi "https://doi.org/10.1002/cber.19891221022" @default.
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