Brønsted-Acid-Catalyzed Synthesis of 3-Alkoxy and 3-Sulfamido Indanones via a Tandem Cyclization
- 22 May 2019
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 84 (13) , 8497-8508
Abstract
Brønsted acid-catalyzed allylic substitution reactions of the in-situ generated 3-hydroxy indanones with alcohols and sulfamides were investigated, which provided a facile route for the synthesis of a large variety of 3-alkoxy and 3-sulfamido indanones. The key intermediates, 3-hydroxy indanones, were obtained through intramolecular Meyer-Schuster rearrangement of o-propargyl alcohol benzaldehydes. The resulting 3-benzyloxy indanone could be selectively modified by allylic sulfonamidation and reduction reactions.Keywords
Funding Information
- Baoji University of Arts And Sciences (ZK16060)
- China Postdoctoral Science Foundation (2016M592826)
- National Natural Science Foundation of China (21702006)
This publication has 67 references indexed in Scilit:
- Enantiodivergent Synthesis of Tertiary α-Aryl 1-Indanones: Evidence Toward Disparate Mechanisms in the Palladium-Catalyzed Decarboxylative Asymmetric ProtonationThe Journal of Organic Chemistry, 2017
- Palladium-Catalyzed Enantioselective α-Arylation of α-FluoroketonesJournal of the American Chemical Society, 2016
- Direct Catalytic Asymmetric Mannich Reactions for the Construction of Quaternary Carbon StereocentersJournal of the American Chemical Society, 2016
- Indanes—Properties, Preparation, and Presence in Ligands for G Protein Coupled ReceptorsMedicinal Research Reviews, 2015
- A Facile Synthesis of Oxoindenothiazine and Dioxospiro(indene‐2,4′‐thiazine) Derivatives from (Substituted ethylidene)hydrazinecarbothioamidesJournal of Heterocyclic Chemistry, 2014
- Asymmetric microbial conversion of (E)-2-benzylideneindan-1-one by the filamentous fungi Botrytis cinerea, Trichoderma viride, and Eutypa lataTetrahedron: Asymmetry, 2011
- Metal-free Michael addition initiated multicomponent oxidative cyclodehydration route to polysubstituted pyridines from 1,3-dicarbonylsChemical Communications, 2008
- Total Synthesis of Resveratrol‐Based Natural Products: A Chemoselective SolutionAngewandte Chemie International Edition, 2007
- A novel three-component reaction for the synthesis of new 4-azafluorenone derivativesTetrahedron, 2007
- Convenient Access to Polysubstituted 1-Indanones by Sc(OTf)3-Catalyzed Intramolecular Friedel−Crafts Acylation of Benzyl Meldrum's Acid DerivativesOrganic Letters, 2003