Online citations, reference lists, and bibliographies.
← Back to Search

1,2- Vs 1,4-Addition Of Acylbenzotriazoles To α,β-Unsaturated Aldehydes And Ketones. A Novel Route To 3-Alkyl-4,6-diaryl-3,4-dihydropyran-2-ones

A. Katritzky, O. Denisko
Published 2002 · Chemistry

Save to my Library
Download PDF
Analyze on Scholarcy
Share
Lithiation of aliphatic 1-acylbenzotriazoles with subsequent reaction with α,β-unsaturated ketones and aldehydes affords either 3,4,6-trisubstituted 3,4-dihydropyran-2-ones or 1,3-dienes depending on the carbonyl reagent used. Substituent effects on product yield and isomer ratio are discussed.



This paper is referenced by
10.1016/B978-008044992-0.00501-0
5.01 1,2,3-Triazoles
S. Rachwał (2008)
10.1002/CJOC.200790318
A Convenient and Efficient Route to 1,4‐Bis(heteroaryl)‐ buta‐1,3‐diene and 4‐Heteroarylbut‐1‐en‐3‐yne from 1,4‐Dichlorobut‐2‐yne
Xiao-Ming Zhang (2007)
10.1016/J.TET.2014.09.022
A new approach to 4,6-disubstituted-3,4-dihydropyran-2-ones by Domino Michael addition-cyclization reaction under PTC conditions
Nicoletta Gaggero (2014)
10.1021/ACS.ORGLETT.6B02558
Michael Addition-Lactonization of Arylacetyl Phosphonate to β,γ-Unsaturated α-Keto Esters for the Synthesis of Chiral syn-3,4-Dihydropyranones and 5,6-Dihydropyranones.
M. Zhang (2016)
10.1016/S0959-6380(02)80010-1
Chapter 5.4 Five membered ring systems: With more than one N atom
L. Yet (2009)
10.1246/CL.2006.1398
Diastereo- and Enantioselective Synthesis of 3-Amino-3,4-dihydropyran-2-ones by Tandem Michael Addition and Lactonization Using a Chiral Quaternary Ammonium Phenoxide
H. Nagao (2006)
10.1016/B978-008044992-0.00608-8
Pyrans and their Benzo Derivatives: Synthesis
M. Brimble (2008)
10.1039/B212004F
4 Heterocyclic chemistry
R. Stockman (2003)
10.1016/J.TET.2019.03.007
Enantioselective synthesis of fused dihydropyranones via squaramide-catalyzed Michael addition/lactonization cascade reaction
Jialing Xian (2019)
10.1021/OL026976T
One-pot three-component reaction for the synthesis of alpha-(aminoethyl)-alpha,beta-enones.
Fabio Bertozzi (2002)
10.1246/CL.2005.514
Stereoselective Synthesis of trans-3,4-Dihydropyran-2-ones by Phenoxide ion-catalyzed Tandem Michael Addition and Lactonization
T. Tozawa (2005)
10.1016/J.TET.2004.12.028
Lewis acid mediated reactions of cyclopropyl aryl ketones with arylaldehydes, facile preparation of 2-(2-hydroxyethyl)-1,3-diarylpropenones
M. Shi (2005)
10.1002/CHIN.200252126
1,2- vs 1,4-Addition of Acylbenzotriazoles to α,β-Unsaturated Aldehydes and Ketones. A Novel Route to 3-Alkyl-4,6-diaryl-3,4-dihydropyran-2-ones.
A. R. Katritzky (2002)
10.1016/J.TET.2009.09.103
Enantioselective synthesis of functionalized 3,4-dihydropyran derivatives organocatalyzed by a novel fluorinated-diphenylprolinolether
C. Yu (2009)
10.1002/EJOC.201402024
N-Heterocyclic Carbene Catalysis as a Tool for Gaining Access to the 3,4-Dihydropyran-2-one Skeleton
D. Albanese (2014)
10.1002/ASIA.200600228
Enantioselective synthesis of 3,4-dihydropyran-2-ones by domino Michael addition and lactonization with new asymmetric organocatalysts: cinchona-alkaloid-derived chiral quaternary ammonium phenoxides.
T. Tozawa (2007)
10.1007/7081_2015_180
Benzotriazole-Mediated Synthesis of Oxygen-Containing Heterocycles
O. Bol'shakov (2015)
10.3987/COM-06-S(K)48
Efficient synthesis of substituted 3-amino-3,4-dihydropyran-2-ones diastereo and enantioselective tandem Michael addition and lactonization between α,β-unsaturated ketones and glycine-derived silyl enolates using a chiral quaternary ammonium phenoxide
H. Nagao (2007)
10.1246/CL.2004.1454
An Efficient Synthesis of 3, 4-Dihydropyran-2-one Derivatives by Lewis Base-catalyzed Tandem Michael Addition and Lactonization
T. Tozawa (2004)
10.1016/J.TET.2008.04.054
Features and applications of reactions of α,β-unsaturated N-acylbenzotriazoles with amino compounds
X. Wang (2008)
Semantic Scholar Logo Some data provided by SemanticScholar