Reduction of indolo[2,3-b]quinoxalines

Engqvist, Robert; Stensland, Birgitta; Bergman, Jan

doi:10.1016/j.tet.2005.02.060

Cited by 9 publications

(4 citation statements)

References 11 publications

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“…To discriminate between the primary amino group and the indazole nitrogen, TFAc and tritylchloride (TrCl) groups were chosen as protections. The trifluoroacetylation , on the amino group of 7 to obtain intermediate 8 was made by switching the THF with DCM and using 2 equiv of trifluoroacetic anhydride (TFAA). In theory, 2 equiv of TFAA are required, because of concomitant acylation at ring nitrogens.…”

Section: Resultsmentioning

confidence: 99%

Development of Scaffold Synthesis for the Preparation of New Insulin-Like Growth Factor 1 Receptor Inhibitors

Candiani

D’Arasmo

Heidempergher

et al. 2009

Org. Process Res. Dev.

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Section: Resultsmentioning

confidence: 99%

Development of Scaffold Synthesis for the Preparation of New Insulin-Like Growth Factor 1 Receptor Inhibitors

Candiani

D’Arasmo

Heidempergher

et al. 2009

Org. Process Res. Dev.

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“…The reduction obviously occurs at the central pyrazine ring, whereby the resulting dihydrophenazine exhibits strong oxidation sensitivity. [53] Furthermore, the reactive nitrogens in the pyrazine ring can be N-alkylated after in situ reduction [54] or acylated. [11] Reductions of thiophene-annulated pyrazines are not literature-known.…”

Section: Redox Reactions Reductionsmentioning

confidence: 99%

Synthesis and Reactivity of Dithienopyrazines**

et al. 2023

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Heteroacenes developed to widely used building blocks in organic semiconductors for application in organic electronics due to their tunable structures and properties concomitant with inherent stability. Here, we report efficient preparation and investigation of so far unknown heterotriacenes, basic anti-and syn-dithienopyrazine 5 and 6. The comparison of the two isomers with respect to electronic properties and follow-up reactions gives insights into structure-property and -reactivity relationships. Examples of transition metal-catalyzed CÀ C crosscoupling reactions of corresponding halogenated derivatives show the practical impact for extended π-conjugated systems applied in optoelectronic devices.

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“…The reduction obviously occurs at the central pyrazine ring, whereby the dihydrophenazine exhibits strong oxidation sensitivity. [53] Furthermore, the reactive nitrogens in the pyrazine ring can be N-alkylated after in-situ reduction [54] or acylated. [11] Reductions of thiophene-fused pyrazines are not literature-known.…”

Section: Reactivity and Follow-up Reactionsmentioning

confidence: 99%

Synthesis and Reactivity of Dithienopyrazines

Bäuerle

Mena‐Osteritz

Kreuzer

2023

Preprint

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Heteroacenes developed to widely used building blocks in organic semiconductors for application in organic electronics due to their tunable structures and properties concomi¬ant with inherent stability. Here, we report efficient preparation and investigation of so far unknown heterotriacenes, basic anti- and syn-dithienopyrazines 5 and 6. The comparison of the two isomers with respect to electronic properties and follow-up reactions gives insights into structure-property and -reactivity relationships. Examples of tran¬sition metal-catalyzed C-C cross-coupling reactions of corresponding halogenated derivatives show the practical impact for extended pi-conjugated systems applied in optoelectronic devices.

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Reduction of indolo[2,3-b]quinoxalines

Cited by 9 publications

References 11 publications

Development of Scaffold Synthesis for the Preparation of New Insulin-Like Growth Factor 1 Receptor Inhibitors

Development of Scaffold Synthesis for the Preparation of New Insulin-Like Growth Factor 1 Receptor Inhibitors

Synthesis and Reactivity of Dithienopyrazines**

Synthesis and Reactivity of Dithienopyrazines

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