An efficient AgOTf catalyzed tandem intramolecular transannulation of ((2-alkynyl)aryl)cyclopropyl ketones leading to the 2,3-dihydronaphtho[1,2-b]furans has been developed. The reaction features a regioselective alkyne hydration, cyclopropylketone-2,3-dyhydrofuran rearrangement, and benzannulation. The methodology gives direct access to the tricyclic core structure of biologically important 2,3-dihydronaphtho[1,2-b]furan natural products.
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http://dx.doi.org/10.1039/c6cc07220h | DOI Listing |
Biochemistry
December 2024
Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States.
Sabinene is a plant natural product with a distinctive strained [3.1.0] bicyclic ring system that is used commercially as a spicy and pine-like fragrance with citrus undertones.
View Article and Find Full Text PDFOrg Lett
November 2023
Department of Chemistry, Tamkang University, New Taipei City 251301, Taiwan, Republic of China.
Herein, we report a nickel-catalyzed intramolecular denitrogenative dual annulation reaction of aryl nitrile-containing 1,2,3-benzotriazine-4(3)-ones to synthesize polycyclic pyrroloquinazolinones with a tolerance of a wide diversity of substituents. This catalytic reaction is the first denitrogenative transannulation of 1,2,3-benzotriazine-4(3)-one with nitrile, which can be applied as the critical step to synthesize luotonin A with a high step economy.
View Article and Find Full Text PDFJ Org Chem
September 2022
Technology for Organic Synthesis Department, Ural Federal University, 19 Mira Street, Yekaterinburg 620002, Russia.
The reactivity of readily available 4,5-fused-1-sulfonyl-1,2,3-triazoles was examined in the Rh(II)-catalyzed transannulation reaction with nitriles. We have come across the interesting observation that 1-sulfonyl cycloalkeno[][1,2,3]triazoles that possess β-hydrogens resist intramolecular β-hydride migration and could serve as a new source of Rh-iminocarbenoids for intermolecular Rh(II)-catalyzed transannulation reactions. As a result, 1-sulfonyl cyclohexeno-, cyclohepteno-, dihydropyrano-, 5-phenyltetrahydrobenzo-, and 4,5-dihydronaphtho[]imidazoles were synthesized from various nitriles in good yields.
View Article and Find Full Text PDFRSC Adv
October 2020
Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences, Peking Union Medical College Beijing 100193 P. R. China +86-10-5783-3290.
A metal-free one-pot intramolecular transannulation of 1-sulfonyl-4-(2-aminomethylphenyl)-1,2,3-triazoles has been developed, which enables the facile synthesis of the various 3-aminoisoquinolines as well as relevant scaffolds from readily available starting materials.
View Article and Find Full Text PDFRSC Adv
February 2020
Department of Chemistry, Takestan Branch, Islamic Azad University Takestan Iran
Dihydronaphthofurans (DHNs) are an important class of arene ring-fused furans which are widely found in many natural and non-natural products and drug candidates with relevant biological and pharmacological activities. Furthermore, vinylidene-naphthofurans exhibit photochromic properties when exposed to UV or sun light at room temperature. For these reasons, a vast array of synthetic procedures for the preparation of dihydronaphthofurans including annulation of naphthols with various reagents, cycloaddition reactions ([3 + 2], [4 + 1] and Diels-Alder), intramolecular transannulation, Friedel-Crafts, Wittig, Claisen rearrangement, neophyl rearrangement and other reactions under various conditions have been developed over the past decades.
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