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

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

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

Affiliations

Univ Basque Country UPV EHU, Dept Organ & Inorgan Chem, 48080 Bilbao, Spain - Author

Abstract

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.

Keywords
Amino-acidsAsymmetric-synthesisC-h activationCamptotheciCascade annulationCatalysisFormal synthesisPolyhydroxylated pyrrolizidine alkaloidsRadical cyclizationRing contractionTopoisomerase-i inhibitors

Quality index

Bibliometric impact. Analysis of the contribution and dissemination channel

The work has been published in the journal JOURNAL OF ORGANIC CHEMISTRY due to its progression and the good impact it has achieved in recent years, according to the agency WoS (JCR), it has become a reference in its field. In the year of publication of the work, 2022, it was in position 10/52, thus managing to position itself as a Q1 (Primer Cuartil), in the category Chemistry, Organic.

Independientemente del impacto esperado determinado por el canal de difusión, es importante destacar el impacto real observado de la propia aportación.

Según las diferentes agencias de indexación, el número de citas acumuladas por esta publicación hasta la fecha 2025-05-02:

  • WoS: 3
  • Scopus: 3
  • OpenCitations: 3
Impact and social visibility

From the perspective of influence or social adoption, and based on metrics associated with mentions and interactions provided by agencies specializing in calculating the so-called "Alternative or Social Metrics," we can highlight as of 2025-05-02:

With a more dissemination-oriented intent and targeting more general audiences, we can observe other more global scores such as:

  • The Total Score from Altmetric: 2.1.
  • The number of mentions on the social network X (formerly Twitter): 4 (Altmetric).

It is essential to present evidence supporting full alignment with institutional principles and guidelines on Open Science and the Conservation and Dissemination of Intellectual Heritage. A clear example of this is:

  • The work has been submitted to a journal whose editorial policy allows open Open Access publication.