doi: 10.3390/molecules15052949.
Regioselective Suzuki-Miyaura reaction: application to the microwave-promoted synthesis of 4,7-diarylquinazolines
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- PMID: 20657457
- PMCID: PMC6263357
- DOI: 10.3390/molecules15052949
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Regioselective Suzuki-Miyaura reaction: application to the microwave-promoted synthesis of 4,7-diarylquinazolines
Molecules.
.
Abstract
New diarylquinazolines displaying pharmaceutical potential were synthesized in high yields from 4,7-dichloro-2-(2-methylprop-1-enyl)-6-nitroquinazoline by using microwave-promoted regioselective Suzuki-Miyaura cross-coupling reactions.
Figures
Synthesis of starting material 5.
Regioselective Suzuki-Miyaura reaction.
Cross coupling reaction at position 7.
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References
-
- Miyaura N., Yamada K., Suzuki A. A new stereospecific cross-coupling by the palladium-catalyzed reaction of 1-alkenylboranes with 1-alkenyl or 1-alkynyl halides. Tetrahedron Lett. 1979;20:3437–3440. doi: 10.1016/S0040-4039(01)95429-2. - DOI
-
- Miyaura N., Suzuki A. Stereoselective synthesis of arylated (E)-alkenes by the reaction of alk-1-enylboranes with aryl halides in the presence of palladium catalyst. J. Chem. Soc. Chem. Commun. 1979:866–867. doi: 10.1039/c39790000866. - DOI
-
- Miyaura N., Suzuki A. Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds. Chem. Rev. 1995;95:2457–2483. doi: 10.1021/cr00039a007. - DOI
-
- Miyaura N. Organoboron Compounds. Top. Curr. Chem. 2002;219:11–59. doi: 10.1007/3-540-45313-X_2. - DOI
-
- Suzuki A., Brown H.C. Organic Syntheses via BoranesVolume 3: Suzuki coupling. Aldrich Chemical Company; Milwaukee, WI, USA: 2003.
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