Brønsted Acid Catalyzed (4 + 2) Cyclocondensation of 3-Substituted Indoles with Donor-Acceptor Cyclopropanes

Ortega, A. ; Uria, U. ; Tejero, T. (Universidad de Zaragoza) ; Prieto, L. ; Reyes, E. ; Merino, P. (Universidad de Zaragoza) ; Vicario, J.L.

Resumen: Acylcyclopropanes are employed as useful donor-acceptor cyclopropanes that undergo formal (4 + 2) cyclocondensation with N-unprotected 3-substituted indoles in the presence of a Brønsted acid catalyst. The reaction involves the simultaneous alkylation of both the N and C-2 positions of the indole and provides access to the 8, 9-dihydropyrido[1, 2-a]indole scaffold that is the central core of several biologically relevant indole alkaloids in excellent yields and good selectivities.

Idioma: Inglés

DOI: 10.1021/acs.orglett.1c00470

Año: 2021

Publicado en: ORGANIC LETTERS 23, 6 (2021), 2326–2331
ISSN: 1523-7060

Factor impacto JCR: 6.072 (2021)

Categ. JCR: CHEMISTRY, ORGANIC rank: 4 / 56 = 0.071 (2021) - Q1 - T1

Factor impacto CITESCORE: 10.4 - Biochemistry, Genetics and Molecular Biology (Q1)

Factor impacto SCIMAGO: 1.669 - Organic Chemistry (Q1) - Biochemistry (Q1)

Financiación: info:eu-repo/grantAgreement/ES/DGA/E34-20R
Financiación: info:eu-repo/grantAgreement/ES/MINECO/PID2019-104090RB-100
Financiación: info:eu-repo/grantAgreement/ES/MINECO-FEDER/CTQ2016-76155-R

Tipo y forma: Article (Published version)

Área (Departamento): Área Química Orgánica (Dpto. Química Orgánica)