NH4OAc Promoted Cyclocondensation of 3-(o-Allylphenyl)pentane-1,5-diones: Synthesis of Tetracyclic Benzofused 1-Azahomoisotwistanes
Authors:
- 20 July 2012
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 14 (15) , 3936-3939
Abstract
A facile two-step synthetic route for preparing the novel tetracyclic skeleton of benzofused 2,6-diaryl-1-azahomoisotwistanes 2 had been developed. The route was carried out by a one-pot tandem cross-coupling reaction of o-allylbenzaldehydes 1 with aryl methyl ketones 3, and NH4OAc mediated the cascade cyclocondensation reaction of the resulting 1,5-diketones 4 with the 3-o-allylphenyl group in good yield in two steps.Keywords
This publication has 39 references indexed in Scilit:
- Recent Strategies for the Synthesis of Pyridine DerivativesChemistry – A European Journal, 2010
- Asymmetric Synthesis of Substituted Homotropinones from N-Sulfinyl β-Amino Ketone Ketals. (−)-Euphococcinine and (−)-AdalineOrganic Letters, 2010
- An Unprecedented Approach to 4,5-Disubstituted Pyrimidine Derivatives by a ZnCl2-Catalyzed Three-Component Coupling ReactionOrganic Letters, 2009
- Lewis Acid-Catalyzed One-Pot, Three-Component Route to Chiral 3,3‘-BipyrrolesOrganic Letters, 2008
- The fascinating construction of pyridine ring systems by transition metal-catalysed [2 + 2 + 2] cycloaddition reactionsChemical Society Reviews, 2007
- Highly Efficient and Direct Heterocyclization of Dipyridyl Ketone to N,N-Bidentate LigandsThe Journal of Organic Chemistry, 2005
- De novo synthesis of substituted pyridinesTetrahedron, 2004
- Efficient Synthesis of Imidazoles from Aldehydes and 1,2-Diketones Using Microwave IrradiationOrganic Letters, 2004
- Reactions of 1,5-Diketones with Ammonia and Its Derivatives. (Review)Chemistry of Heterocyclic Compounds, 2003
- Construction of Pyridine Rings by Metal-Mediated [2 + 2 + 2] CycloadditionChemical Reviews, 2003