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Pyrrolodiazines. 6. Palladium-catalyzed arylation, heteroarylation, and amination of 3,4-dihydropyrrolo[1,2-a]pyrazines.
J Org Chem. 2004 Dec 10; 69(25):8668-75.JO

Abstract

The palladium-catalyzed Suzuki cross-coupling reaction of arylboronic acids and 6-bromo- and 6,8-dibromo-3,4-dihydropyrrolo[1,2-a]pyrazines afforded 6-substituted and 6,8-disubstituted 3,4-dihydropyrrolo[1,2-a]pyrazines in good yields. Stille and Negishi coupling reactions have been used to prepare 6-heteroaryl-substituted derivatives in moderate yields by employing heteroaryl halides and 6-metalated 3,4-dihydropyrrolo[1,2-a]pyrazines as reaction partners. A variety of cyclic secondary amines have also been incorporated at position C-6 of 6-bromo-1-phenyl-3,4-dihydropyrrolo[1,2-a]pyrazine in the presence of the palladium catalyst Pd(2)(dba)(3) in conjunction with BINAP as ligand. This amination reaction is one of the few reported examples of such a palladium-catalyzed transformation on a pyrrole ring, although the reaction could not be extended to less nucleophilic amines.

Authors+Show Affiliations

Castellote I
Departamento de Química Orgánica, Universidad de Alcalá, 28871-Alcalá de Henares, Madrid, Spain.
Vaquero JJ
No affiliation info available
Fernández-Gadea J
No affiliation info available
Alvarez-Builla J
No affiliation info available

MeSH

AlkylationAminationCatalysisMolecular StructurePalladiumPyrazinesPyrroles

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

15575742

Citation

Castellote, Isabel, et al. "Pyrrolodiazines. 6. Palladium-catalyzed Arylation, Heteroarylation, and Amination of 3,4-dihydropyrrolo[1,2-a]pyrazines." The Journal of Organic Chemistry, vol. 69, no. 25, 2004, pp. 8668-75.
Castellote I, Vaquero JJ, Fernández-Gadea J, et al. Pyrrolodiazines. 6. Palladium-catalyzed arylation, heteroarylation, and amination of 3,4-dihydropyrrolo[1,2-a]pyrazines. J Org Chem. 2004;69(25):8668-75.
Castellote, I., Vaquero, J. J., Fernández-Gadea, J., & Alvarez-Builla, J. (2004). Pyrrolodiazines. 6. Palladium-catalyzed arylation, heteroarylation, and amination of 3,4-dihydropyrrolo[1,2-a]pyrazines. The Journal of Organic Chemistry, 69(25), 8668-75.
Castellote I, et al. Pyrrolodiazines. 6. Palladium-catalyzed Arylation, Heteroarylation, and Amination of 3,4-dihydropyrrolo[1,2-a]pyrazines. J Org Chem. 2004 Dec 10;69(25):8668-75. PubMed PMID: 15575742.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Pyrrolodiazines. 6. Palladium-catalyzed arylation, heteroarylation, and amination of 3,4-dihydropyrrolo[1,2-a]pyrazines. AU - Castellote,Isabel, AU - Vaquero,Juan J, AU - Fernández-Gadea,Javier, AU - Alvarez-Builla,Julio, PY - 2004/12/4/pubmed PY - 2005/2/16/medline PY - 2004/12/4/entrez SP - 8668 EP - 75 JF - The Journal of organic chemistry JO - J Org Chem VL - 69 IS - 25 N2 - The palladium-catalyzed Suzuki cross-coupling reaction of arylboronic acids and 6-bromo- and 6,8-dibromo-3,4-dihydropyrrolo[1,2-a]pyrazines afforded 6-substituted and 6,8-disubstituted 3,4-dihydropyrrolo[1,2-a]pyrazines in good yields. Stille and Negishi coupling reactions have been used to prepare 6-heteroaryl-substituted derivatives in moderate yields by employing heteroaryl halides and 6-metalated 3,4-dihydropyrrolo[1,2-a]pyrazines as reaction partners. A variety of cyclic secondary amines have also been incorporated at position C-6 of 6-bromo-1-phenyl-3,4-dihydropyrrolo[1,2-a]pyrazine in the presence of the palladium catalyst Pd(2)(dba)(3) in conjunction with BINAP as ligand. This amination reaction is one of the few reported examples of such a palladium-catalyzed transformation on a pyrrole ring, although the reaction could not be extended to less nucleophilic amines. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/15575742/Pyrrolodiazines__6__Palladium_catalyzed_arylation_heteroarylation_and_amination_of_34_dihydropyrrolo[12_a]pyrazines_ DB - PRIME DP - Unbound Medicine ER -