CuSO4–Glucose for in Situ Generation of Controlled Cu(I)–Cu(II) Bicatalysts: Multicomponent Reaction of Heterocyclic Azine and Aldehyde with Alkyne, and Cycloisomerization toward Synthesis of N-Fused Imidazoles
- 9 April 2012
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 77 (9) , 4438-4444
Abstract
The catalytic efficiency of mixed Cu(I)–Cu(II) system in situ generated by partial reduction of CuSO4 with glucose in ethanol (nonanhydrous) under open air has been explored. With this catalysis, the multicomponent cascade reaction of A3-coupling of heterocyclic amidine with aldehyde and alkyne, 5-exo-dig cycloisomerization, and prototropic shift has afforded an efficient and eco-friendly synthesis of therapeutically important versatile N-fused imidazoles. Diverse heterocyclic amidines, several of which are known to be poorly reactive, and aldehydes are compatible in this catalytic process.Keywords
This publication has 34 references indexed in Scilit:
- Gold-Catalyzed Three-Component Tandem Process: An Efficient and Facile Assembly of Complex Butenolides from Alkynes, Amines, and Glyoxylic AcidJournal of the American Chemical Society, 2010
- Efficient and General Synthesis of 3-Aminoindolines and 3-Aminoindoles via Copper-Catalyzed Three-Component Coupling ReactionAdvanced Synthesis & Catalysis, 2010
- Facile and efficient synthesis of polyfunctionalized benzofurans: three-component coupling reactions from an alkynylsilane, an o-hydroxybenzaldehyde derivative, and a secondary amine by a Cu(I)–Cu(II) cooperative catalytic systemTetrahedron Letters, 2008
- Sequential catalytic process: synthesis of quinoline derivatives by AuCl3/CuBr-catalyzed three-component reaction of aldehydes, amines, and alkynesTetrahedron, 2008
- Efficient Preparation of the Isoindoline Framework via a Six Component, Tandem Double A3‐Coupling and [2+2+2] Cycloaddition ReactionAdvanced Synthesis & Catalysis, 2008
- Gold-Catalyzed Multicomponent Synthesis of Aminoindolizines from Aldehydes, Amines, and Alkynes under Solvent-Free Conditions or in WaterOrganic Letters, 2007
- Direct addition of alkynes to imines and related CN electrophiles: A convenient access to propargylaminesChemical Communications, 2006
- Direct Mannich and Nitro‐Mannich Reactions with Non‐Activated Imines: AgOTf‐Catalyzed Addition of Pronucleophiles to ortho‐Alkynylaryl Aldimines Leading to 1,2‐DihydroisoquinolinesAngewandte Chemie International Edition, 2005
- A Silver-Catalyzed Domino Route toward 1,2-Dihydroquinoline Derivatives from Simple Anilines and AlkynesOrganic Letters, 2005
- Cu(I)-catalyzed direct addition and asymmetric addition of terminal alkynes to iminesProceedings of the National Academy of Sciences, 2004