Copper(II)-Catalyzed (3+2) Cycloaddition of 2H-Azirines to Six-Membered Cyclic Enols as a Route to Pyrrolo[3,2-c]quinolone, Chromeno[3,4-b]pyrrole, and Naphtho[1,8-ef]indole Scaffolds

A method for the [2+3] pyrroline annulation to the six-membered non-aromatic enols using 3-aryl-2H-azirines as annulation agents is developed in the current study. The reaction proceeds as a formal (3+2) cycloaddition via the N1-C2 azirine bond cleavage and is catalyzed by both Cu(II) and Cu(I) comp...

Descripción completa

Detalles Bibliográficos
Autores principales: Sakharov, Pavel A., Rostovskii, Nikolai V., Khlebnikov, Alexander F., Novikov, Mikhail S.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9457675/
https://www.ncbi.nlm.nih.gov/pubmed/36080448
http://dx.doi.org/10.3390/molecules27175681
_version_ 1784786114082504704
author Sakharov, Pavel A.
Rostovskii, Nikolai V.
Khlebnikov, Alexander F.
Novikov, Mikhail S.
author_facet Sakharov, Pavel A.
Rostovskii, Nikolai V.
Khlebnikov, Alexander F.
Novikov, Mikhail S.
author_sort Sakharov, Pavel A.
collection PubMed
description A method for the [2+3] pyrroline annulation to the six-membered non-aromatic enols using 3-aryl-2H-azirines as annulation agents is developed in the current study. The reaction proceeds as a formal (3+2) cycloaddition via the N1-C2 azirine bond cleavage and is catalyzed by both Cu(II) and Cu(I) compounds. The new annulation method can be applied to prepare pyrrolo[3,2-c]quinoline, chromeno[3,4-b]pyrrole, and naphtho[1,8-ef]indole derivatives in good to excellent yields from enols of the quinolin-2-one, 2H-chromen-2-one, and 1H-phenalen-1-one series.
format Online
Article
Text
id pubmed-9457675
institution National Center for Biotechnology Information
language English
publishDate 2022
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-94576752022-09-09 Copper(II)-Catalyzed (3+2) Cycloaddition of 2H-Azirines to Six-Membered Cyclic Enols as a Route to Pyrrolo[3,2-c]quinolone, Chromeno[3,4-b]pyrrole, and Naphtho[1,8-ef]indole Scaffolds Sakharov, Pavel A. Rostovskii, Nikolai V. Khlebnikov, Alexander F. Novikov, Mikhail S. Molecules Article A method for the [2+3] pyrroline annulation to the six-membered non-aromatic enols using 3-aryl-2H-azirines as annulation agents is developed in the current study. The reaction proceeds as a formal (3+2) cycloaddition via the N1-C2 azirine bond cleavage and is catalyzed by both Cu(II) and Cu(I) compounds. The new annulation method can be applied to prepare pyrrolo[3,2-c]quinoline, chromeno[3,4-b]pyrrole, and naphtho[1,8-ef]indole derivatives in good to excellent yields from enols of the quinolin-2-one, 2H-chromen-2-one, and 1H-phenalen-1-one series. MDPI 2022-09-02 /pmc/articles/PMC9457675/ /pubmed/36080448 http://dx.doi.org/10.3390/molecules27175681 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Sakharov, Pavel A.
Rostovskii, Nikolai V.
Khlebnikov, Alexander F.
Novikov, Mikhail S.
Copper(II)-Catalyzed (3+2) Cycloaddition of 2H-Azirines to Six-Membered Cyclic Enols as a Route to Pyrrolo[3,2-c]quinolone, Chromeno[3,4-b]pyrrole, and Naphtho[1,8-ef]indole Scaffolds
title Copper(II)-Catalyzed (3+2) Cycloaddition of 2H-Azirines to Six-Membered Cyclic Enols as a Route to Pyrrolo[3,2-c]quinolone, Chromeno[3,4-b]pyrrole, and Naphtho[1,8-ef]indole Scaffolds
title_full Copper(II)-Catalyzed (3+2) Cycloaddition of 2H-Azirines to Six-Membered Cyclic Enols as a Route to Pyrrolo[3,2-c]quinolone, Chromeno[3,4-b]pyrrole, and Naphtho[1,8-ef]indole Scaffolds
title_fullStr Copper(II)-Catalyzed (3+2) Cycloaddition of 2H-Azirines to Six-Membered Cyclic Enols as a Route to Pyrrolo[3,2-c]quinolone, Chromeno[3,4-b]pyrrole, and Naphtho[1,8-ef]indole Scaffolds
title_full_unstemmed Copper(II)-Catalyzed (3+2) Cycloaddition of 2H-Azirines to Six-Membered Cyclic Enols as a Route to Pyrrolo[3,2-c]quinolone, Chromeno[3,4-b]pyrrole, and Naphtho[1,8-ef]indole Scaffolds
title_short Copper(II)-Catalyzed (3+2) Cycloaddition of 2H-Azirines to Six-Membered Cyclic Enols as a Route to Pyrrolo[3,2-c]quinolone, Chromeno[3,4-b]pyrrole, and Naphtho[1,8-ef]indole Scaffolds
title_sort copper(ii)-catalyzed (3+2) cycloaddition of 2h-azirines to six-membered cyclic enols as a route to pyrrolo[3,2-c]quinolone, chromeno[3,4-b]pyrrole, and naphtho[1,8-ef]indole scaffolds
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9457675/
https://www.ncbi.nlm.nih.gov/pubmed/36080448
http://dx.doi.org/10.3390/molecules27175681
work_keys_str_mv AT sakharovpavela copperiicatalyzed32cycloadditionof2hazirinestosixmemberedcyclicenolsasaroutetopyrrolo32cquinolonechromeno34bpyrroleandnaphtho18efindolescaffolds
AT rostovskiinikolaiv copperiicatalyzed32cycloadditionof2hazirinestosixmemberedcyclicenolsasaroutetopyrrolo32cquinolonechromeno34bpyrroleandnaphtho18efindolescaffolds
AT khlebnikovalexanderf copperiicatalyzed32cycloadditionof2hazirinestosixmemberedcyclicenolsasaroutetopyrrolo32cquinolonechromeno34bpyrroleandnaphtho18efindolescaffolds
AT novikovmikhails copperiicatalyzed32cycloadditionof2hazirinestosixmemberedcyclicenolsasaroutetopyrrolo32cquinolonechromeno34bpyrroleandnaphtho18efindolescaffolds

Ejemplares similares