Application of Suzuki-Miyaura and Buchwald-Hartwig Cross-coupling Reactions to the Preparation of Substituted 1,2,4-Benzotriazine 1-Oxides Related to the Antitumor Agent Tirapazamine.

Autor: Sarkar U; University of Missouri, Department of Chemistry, 125 Chemistry Building, Columbia, MO 65211., Hillebrand R; University of Missouri, Department of Chemistry, 125 Chemistry Building, Columbia, MO 65211., Johnson KM; University of Missouri, Department of Chemistry, 125 Chemistry Building, Columbia, MO 65211., Cummings AH; University of Missouri, Department of Chemistry, 125 Chemistry Building, Columbia, MO 65211., Phung NL; University of Missouri, Department of Chemistry, 125 Chemistry Building, Columbia, MO 65211., Rajapakse A; University of Missouri, Department of Chemistry, 125 Chemistry Building, Columbia, MO 65211., Zhou H; University of Missouri, Department of Chemistry, 125 Chemistry Building, Columbia, MO 65211., Willis JR; University of Missouri, Department of Chemistry, 125 Chemistry Building, Columbia, MO 65211., Barnes CL; University of Missouri, Department of Chemistry, 125 Chemistry Building, Columbia, MO 65211., Gates KS; University of Missouri, Department of Chemistry, 125 Chemistry Building, Columbia, MO 65211.; University of Missouri, Department of Biochemistry, 125 Chemistry Building, Columbia, MO 65211.
Jazyk: angličtina
Zdroj: Journal of heterocyclic chemistry [J Heterocycl Chem] 2017 Jan; Vol. 54 (1), pp. 155-160. Date of Electronic Publication: 2015 Nov 25.
DOI: 10.1002/jhet.2559
Abstrakt: Many 1,2,4-benzotriazine 1,4-dioxides display the ability to selectively kill the oxygen-poor cells found in solid tumors. As a result, there is a desire for synthetic routes that afford access to substituted 1,2,4-benzotriazine 1-oxides that can be used as direct precursors in the synthesis of 1,2,4-benzotriazine 1,4-dioxides. Here we describe the use of Suzuki-Miyaura and Buchwald-Hartwig cross-coupling reactions for the construction of various 1,2,4-benzotriazine 1-oxide analogs bearing substituents at the 3-, 6-, and 7-positions.
Databáze: MEDLINE
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