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The authors thank the Spanish Agencia Estatal de Investigacion (FEDER-PID2020-118422-GB-I00 and FPI fellowship to A.S.) , the Basque Government (IT908-16 and postdoctoral contract to J.L.B.) , and UPV/EHU (fellowship to E.C.) for financial support.

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Transannular Approach to 2,3-Dihydropyrrolo[1,2-b]isoquinolin-5(1H)-ones through Bronsted Acid-Catalyzed Amidohalogenation

Publicado en:JOURNAL OF ORGANIC CHEMISTRY. 87 (15): 10062-10072 - 2022-07-26 87(15), DOI: 10.1021/acs.joc.2c01045

Autores: Capel, Estefania; Luis-Barrera, Javier; Sorazu, Ana; Uria, Uxue; Prieto, Liher; Reyes, Efraim; Carrillo, Luisa; Vicario, Jose L

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A transannular approach has been developed for the construction of pyrrolo[1,2-b]isoquinolinones starting from benzofused nine-membered enelactams. This process takes place in the presence of a halogenating agent and under Bronsted acid catalysis and proceeds via a transannular amidohalogenation, followed by elimination. The reaction has been found to be wide in scope, enabling the formation of a variety of tricyclic products in good overall yield, regardless of the substitution pattern in the initial lactam substrate. The reaction has also been applied to the total synthesis of a reported topoisomerase I inhibitor and to the formal synthesis of rosettacin. Further extension of this methodology allows the preparation of 10-iodopyrrolo[1,2-b]isoquinolinones by using an excess of halogenating agent and these compounds can be further manipulated through standard Suzuki coupling chemistry into a variety of 10-aryl-substituted pyrrolo[1,2-b]isoquinolinones.

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