Palladium iodide-catalyzed selective carbonylative double cyclization of 4-(2-aminophenyl)-3-yn-1-ols to dihydrofuroquinolinone derivatives

Article

Mancuso, R., De Salvo, A., Russo, P., Falcicchio, A., Ca’, N.D., Pantoja Munoz, L. and Gabriele, B. 2023. Palladium iodide-catalyzed selective carbonylative double cyclization of 4-(2-aminophenyl)-3-yn-1-ols to dihydrofuroquinolinone derivatives. Chinese Journal of Chemistry. 41 (21), pp. 2801-2809. https://doi.org/10.1002/cjoc.202300277
TypeArticle
TitlePalladium iodide-catalyzed selective carbonylative double cyclization of 4-(2-aminophenyl)-3-yn-1-ols to dihydrofuroquinolinone derivatives
AuthorsMancuso, R., De Salvo, A., Russo, P., Falcicchio, A., Ca’, N.D., Pantoja Munoz, L. and Gabriele, B.
Abstract

The PdI2/KI‐catalyzed oxidative carbonylation of 4‐(2‐aminophenyl)‐3‐yn‐1‐ols, bearing two potential nucleophilic groups in suitable position selectively leads to dihydrofuroquinolinone derivatives in fair to high yields (60%—89%) and excellent turnover numbers (180—267 mol of product per mol of Pd) over 19 examples, through a mechanistic pathway involving initial O‐cyclization followed by N‐cyclocarbonylation. In such process, the selective catalytic construction of two rings and three new bonds is achieved in one synthetic step to afford high value added fused heterocyclic structures starting from readily available materials.

KeywordsCarbonylation; Cyclization; Heterocycles; Palladium; Polycyclic heterocycles
Sustainable Development Goals12 Responsible consumption and production
Middlesex University ThemeCreativity, Culture & Enterprise
PublisherWiley
JournalChinese Journal of Chemistry
ISSN1001-604X
Electronic1614-7065
Publication dates
Online26 Jul 2023
Print01 Nov 2023
Publication process dates
Submitted04 May 2023
Accepted26 Jun 2023
Deposited16 Oct 2024
Output statusPublished
Publisher's version
License
File Access Level
Open
Copyright Statement

© 2023 The Authors. Chinese Journal of Chemistry published by SIOC, CAS, Shanghai and Wiley-VCH GmbH
This is an open access article under the terms of the Creative Commons Attribution-NonCommercial-NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made.

Digital Object Identifier (DOI)https://doi.org/10.1002/cjoc.202300277
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