Dihydropyridine-based multicomponent reactions. Ef...[Org Lett. 2003]

SearchDatabase nameforSearch term

Advanced Search

Your browser version may not work well with NCBI's Web applications. More information here...

Display Show

All: 1

Review: 0

Click to change filter selection through MyNCBI.

1: Org Lett. 2003 Mar 6;5(5):717-20. Links

Dihydropyridine-based multicomponent reactions. Efficient entry into new tetrahydroquinoline systems through Lewis acid-catalyzed formal [4 + 2] cycloadditions.

Lavilla R, Bernabeu MC, Carranco I, Díaz JL.

Parc Científic de Barcelona, University of Barcelona, Josep Samitier 1-5, 08028-Barcelona, Spain. rlavilla@pcb.ub.es

The three-component reaction of dihydropyridines, aldehydes, and p-methylaniline efficiently forms highly substituted tetrahydroquinolines in a stereoselective manner through a Lewis acid-catalyzed formal [4 + 2] cycloaddition. InCl(3) and Sc(OTf)(3) are the catalysts of choice for this process. The in situ generation of a reactive 1,4-dihydropyridine through the regioselective nucleophilic addition of cyanide to pyridinium salts allows a one-pot four-component transformation.

PMID: 12605498 [PubMed - indexed for MEDLINE]

Dihydropyridines in MCRs. Tandem processes leading to modular tetrahydroquinoline systems with up to 6 diversity elements.
Mol Divers. 2003; 6(3-4):171-5.

[Mol Divers. 2003]
Multicomponent reactions with dihydroazines: efficient synthesis of a diverse set of pyrido-fused tetrahydroquinolines.
J Comb Chem. 2005 Jan-Feb; 7(1):33-41.

[J Comb Chem. 2005]
InCl(3)-catalyzed domino reaction of aromatic amines with cyclic enol ethers in water: a highly efficient synthesis of new 1,2,3,4-tetrahydroquinoline derivatives.
J Org Chem. 2002 May 31; 67(11):3969-71.

[J Org Chem. 2002]
The first aza Diels-Alder reaction involving an alpha,beta-unsaturated hydrazone as the dienophile: stereoselective synthesis of C-4 functionalized 1,2,3,4-tetrahydroquinolines containing a quaternary stereocenter.
Org Biomol Chem. 2007 May 7; 5(9):1351-3. Epub 2007 Apr 4.

[Org Biomol Chem. 2007]
ReviewLewis super-acid catalyzed cyclizations: a new route to fragrance compounds.
Chem Biodivers. 2008 Jun; 5(6):1070-82.

[Chem Biodivers. 2008]
» See reviews... | » See all...

Recent Activity

Clear Turn Off Turn On

Dihydropyridine-based multicomponent reactions. Efficient entry into new tetrahydroquinoli...Dihydropyridine-based multicomponent reactions. Efficient entry into new tetrahydroquinoline systems through Lewis acid-catalyzed formal [4 + 2] cycloadditions.

Your browsing activity is empty.

Activity recording is turned off.

Turn recording back on

Display Show

Dihydropyridine-based multicomponent reactions. Efficient entry into new tetrahydroquinoline systems through Lewis acid-catalyzed formal [4 + 2] cycloadditions.

Related articles

Recent Activity