Chemoselective Reduction of Nitroarenes in the Presence of Acid-Sensitive Functional Groups:  Solid-Phase Syntheses of Amino Aryl Azides and Benzotriazoles

Zimmermann, V.; Avemaria, and Frank; Bräse, Stefan

doi:10.1021/cc060116c

Cited by 22 publications

(10 citation statements)

References 12 publications

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“…Katritzky et al reported a method based on the reaction of polymer-supported o -phenylendiamine with isoamyl nitrite . Another article describes the preparation of benzotriazoles from the resin-bound triazene precursors. , We tried to introduce the nitrogen atom to molecule 2 by means of Katritzky method with isoamyl nitrite, but the reaction afforded product 4 only as part of a mixture with other unidentified compounds.…”

Section: Resultsmentioning

confidence: 99%

4-Chloro-2-Fluoro-5-Nitrobenzoic Acid as a Possible Building Block for Solid-phase Synthesis of Various Heterocyclic Scaffolds

et al. 2013

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4-Chloro-2-fluoro-5-nitrobenzoic acid is a commercially available multireactive building block that can serve as a starting material in heterocyclic oriented synthesis (HOS) leading to various condensed nitrogenous cycles. This work describes its ability for the preparation of substituted nitrogenous heterocycles having 5-7-membered cycles via polymer-supported o-phenylendiamines. Immobilization of this compound on Rink resin followed by further chlorine substitution, reduction of a nitro group and appropriate cyclization afforded benzimidazoles, benzotriazoles, quinoxalinones, benzodiazepinediones and succinimides. The method developed is suitable for the synthesis of diverse libraries including the mentioned types of heterocycles, which have significant importance in current drug discovery. In this paper, we also report limitation of these method and unsuccessful attempt to prepare an 8-membered benzodiazocine cycle.

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Section: Resultsmentioning

confidence: 99%

4-Chloro-2-Fluoro-5-Nitrobenzoic Acid as a Possible Building Block for Solid-phase Synthesis of Various Heterocyclic Scaffolds

et al. 2013

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“…• Die wichtigsten methodischen Fortschritte bei der organischen Synthese an der festen Phase umfassen eine chemoselektive Reduktionsmethode von Nitroaromaten mit Na2S und Dioctylviologen121 sowie den eleganten Aufbau von aromatischen Verbindungen mit Ru‐katalysierter [2 2 2]‐Cyclotrimerisierung von Alkinen 122. Weiterhin verstärkt sich der Trend, der strukturellen Diversität der erzeugten Substanzbibliotheken größere Aufmerksamkeit zu schenken 123…”

Section: Festphasensyntheseunclassified

Organische Chemie 2007

Bräse¹

2008

Nachr Chem

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“…Very recently, Bräse et al have reported the chemoselective reduction of solid-phase bound nitroarenes with dioctyl viologen as a single-electron-transfer catalyst and sodium sulfide as a stoichiometric reductant. [19]…”

Section: Single-electron-transfer Reagents In Sposmentioning

confidence: 99%

Electrons as a Reagent in Solid‐Phase Organic Synthesis

Mentel

Breinbauer

2007

Eur J Org Chem

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Solid-Phase Organic Synthesis (SPOS) has become an important tool for the high-throughput synthesis of bioactive molecules or new catalysts. The main advantage of this approach is the covalent attachment of the substrate to an insoluble support, enabling reaction workup through simple filtration. However, the heterogeneous nature of SPOS imposes limitations on the organic reactions applicable on solid phase. Electron-transfer reactions and electroorganic synthesis are reaction types that have not yet received much attention in this context. In this review the current status of electrontransfer reactions carried out on solid phase is described and future developments are discussed. Abbreviations

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Chemoselective Reduction of Nitroarenes in the Presence of Acid-Sensitive Functional Groups: Solid-Phase Syntheses of Amino Aryl Azides and Benzotriazoles

Cited by 22 publications

References 12 publications

4-Chloro-2-Fluoro-5-Nitrobenzoic Acid as a Possible Building Block for Solid-phase Synthesis of Various Heterocyclic Scaffolds

4-Chloro-2-Fluoro-5-Nitrobenzoic Acid as a Possible Building Block for Solid-phase Synthesis of Various Heterocyclic Scaffolds

Organische Chemie 2007

Electrons as a Reagent in Solid‐Phase Organic Synthesis

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