Solid-Phase Synthesis of 1,2-Diketones via Acetylene Oxidation: A Versatile Diversity Platform for the Combinatorial Synthesis of Heterocycles

Abstract

Investigations towards the solid-phase synthesis of 1,2diketones via the oxidation of acetylenes and their use in the combinatorial synthesis of heterocycles such as imidazoles and quinoxalines are described.

Search for Alternative Two‐Step‐Absorption Photoinitiators for 3D Laser Nanoprinting

“…[38,39] Nitrobenzils m-and p-NB, CBZ, and HBZ are synthesized from corresponding symmetric diarylacetylenes by oxidation. [40][41][42][43] The bisimine is synthesized via an aldimine coupling reaction. [44] Finally, Me 4 CPD is furnished from the oxidation of the corresponding commercially available monoketone employing selenium dioxide.…”

Present status of quinoxaline motifs: Excellent pathfinders in therapeutic medicine

“…<<<<Scheme 12>>>> (b) Also, polymer-linked 2-nitrophenylcarbamate was treated with α-bromoketones followed by reduction of the nitro group after which spontaneous intramolecular cyclization took place to give the polymer bound quinoxaline 38 through aerial oxidation and finally cleaved to produce 2-substitutedquinoxaline derivatives 39 (Scheme 13) [63]. <<<<Scheme 13>>>> (c) A straightforward synthesis of 2,3-diarylatedquinoxaline derivatives 40 was achieved by condensation of o-phenylenediamine with solid-phase synthesized diketone as reported by Griebenow and Meyer [65]. As shown in Scheme 14, the diketone intermediate was obtained from strategic oxidation of resin-bound diaryl acetylene which was easily accessible through Sonogashira coupling of aryl halides with terminal alkynes [65].…”

“…<<<<Scheme 13>>>> (c) A straightforward synthesis of 2,3-diarylatedquinoxaline derivatives 40 was achieved by condensation of o-phenylenediamine with solid-phase synthesized diketone as reported by Griebenow and Meyer [65]. As shown in Scheme 14, the diketone intermediate was obtained from strategic oxidation of resin-bound diaryl acetylene which was easily accessible through Sonogashira coupling of aryl halides with terminal alkynes [65]. <<<<Scheme 14>>>> (d) Wu and Ede reported the solid-phase synthesis of 3-phenylquinoxaline-6-carboxamide 41 developed on SynPhase™ Lanterns [66].…”