+ Site Statistics
+ Search Articles
+ PDF Full Text Service
How our service works
Request PDF Full Text
+ Follow Us
Follow on Facebook
Follow on Twitter
Follow on LinkedIn
+ Subscribe to Site Feeds
Most Shared
PDF Full Text
+ Translate
+ Recently Requested

Inverse electron demand diels alder reactions of 4 6 di methyl 2 oxo 2h pyran 5 carboxylic acid esters and morpholino enamines regiospecific preparation of 3 substituted or 4 substituted 2 6 di methyl benzoates



Inverse electron demand diels alder reactions of 4 6 di methyl 2 oxo 2h pyran 5 carboxylic acid esters and morpholino enamines regiospecific preparation of 3 substituted or 4 substituted 2 6 di methyl benzoates



Journal of Organic Chemistry 48(25): 4869-4873



Previously, .alpha.-pyrones have been used as dienes in cycloaddition reactions with enamines to form adducts that, upon elimination of CO2 via a cycloreversion reaction and concomitant aromatization through amine elimination, provided substituted aryl derivatives; however, the regioselectivity of this reaction was not determined. The Diels-Alder reaction of methyl or ethyl 4,6-dimethyl-2-oxo-2H-pyran-5-carboxylate with morpholino enamines is regiospecific. By proper choice of enamine either of the isomeric 2,6-dimethylbenzoates may be obtained as a single product. In several cases a single regioisomeric dihydrobenzoate, which results from elimination of CO2 from the initial cycloadduct, was isolated and characterized [of possible ultility in pyrethroid synthesis].

Please choose payment method:






(PDF emailed within 1 workday: $29.90)

Accession: 005746184

Download citation: RISBibTeXText


Related references

Inverse electron demand Diels-Alder reactions of indole V Reactions of 3-substituted indoles with heteroaromatic azadienes. Tetrahedron Letters 37(29): 5061-5064, 1996

Inverse electron demand diels-alder reactions of 3-substituted indoles Synthesis of the Aspidosperma and Iboga alkaloidal skeleta. Abstracts of Papers American Chemical Society 216(1-3): ORGN 544, 1998

Regiospecific Syntheses of 3-Aza-α-carbolines via Inverse Electron-Demand Diels-Alder Reactions of 2-Aminoindoles with 1,3,5-Triazines. Synlett 2009(19): 3206-3210, 2009

A Convenient Synthesis of Methyl 4-Substituted Benzoates via Diels-Alder Reaction in the Presence of Palladium on Activated Carbon. Synthetic Communications 24(22): 3307-3313, 1994

Electron Deficient Dienes. 2. One Step Synthesis of a Coumarin-Fused Electron Deficient Diene and its Inverse Electron Demand Diels-Alder Reactions with Enamines. Synlett 1999(4): 477-479, 1999

Simultaneously electrogenerated cycloaddition partners for regiospecific inverse-electron-demand Diels-Alder reactions: a route for polyfunctionalized 1,4-benzoxazine derivatives. Journal of Organic Chemistry 69(3): 882-890, 2004

Electron Deficient Dienes 3:Rapid Access to 2-Hydroxybenzophenones via Inverse Electron Demand Diels-Alder-Driven Domino Reactions of a Chromone-Fused Electron Deficient Diene with Enamines. Synlett 2: 0179-0182, 2003

Functionally substituted pyridines by hetero diels alder reaction with inverse electron demand. Chemische Berichte 120(9): 1505-1509, 1987

Electron-deficient dienes. 5. An inverse-electron-demand Diels-Alder approach to 2-substituted 4-methoxyxanthones and 3,4-dimethoxyxanthones. Organic Letters 10(2): 233-236, 2008

First inverse electron-demand Diels-Alder methodology of 3-chloroindoles and methyl coumalate to carbazoles. Organic Letters 16(4): 1124-1127, 2014

Preparation of carbohydrate arrays by using Diels-Alder reactions with inverse electron demand. Chemistry 18(21): 6548-6554, 2012

Asymmetric diels alder reactions inverse electron demand reactions of esters of 3 hydroxypyran 2 one with vinyl ethers use of high pressure to avoid decarboxylation of adducts. Tetrahedron Letters 32(27): 3147-3150, 1991

Asymmetric Diels-Alder and inverse-electron-demand hetero-Diels-Alder reactions of β,γ-unsaturated α-ketoesters with cyclopentadiene catalyzed by N,N'-dioxide copper(II) complex. Chemistry 16(39): 11963-8, 2010

Synthesis of 6H-dibenzo[b,d]pyran-6-ones using the inverse electron demand Diels-Alder reaction. Journal of Organic Chemistry 76(21): 9015-9030, 2011

The 'inverse electron-demand' Diels-Alder reaction in polymer synthesis. Part 5: Preparation and model reactions of some electron-rich bis-dienamines. Tetrahedron 60(15): 3421-3425, 2004