ChemInform Abstract: An Improved Synthesis of 2-Substituted-3-furoic Acids Leading to an Intramolecular Diels-Alder Reaction Between a Dienophile and Furan Diene Both Containing an Electron-Withdrawing Group.

A series of pyrano[4,3-b][1]benzopyranones (7a–t) were synthesized through hetero-Diels-Alder reaction of substituted 3-formylchromones (5) with enol ethers (6), characterized by IR, 1H NMR, 13C NMR, and mass spectral techniques. All the compounds were evaluated for antimicrobial activity against various bacterial and fungal strains, found to possess significant inhibitory potential, particularly, compounds bearing electron withdrawing group -fluoro such as 7i and 7h. Compounds were also tested and displayed a significant inhibitory potential against methicillin-resistant Staphylococcus aureus (MRSA).

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Diels-Alder Reaction of 1,3-Butadiene Derivatives with 1-Methyl-2(1H)-quinolones Having an Electron-Withdrawing Group at the 4-Position.

Chemical and Pharmaceutical Bulletin ◽

10.1248/cpb.49.900 ◽

2001 ◽

Vol 49 (7) ◽

pp. 900-904 ◽

Cited By ~ 9

Author(s):

Reiko FUJITA ◽

Kazuhiro WATANABE ◽

Toshiteru YOSHISUJI ◽

Hiroshi HONGO ◽

Hisao MATSUZAKI

Keyword(s):

Alder Reaction ◽

Diels Alder ◽

Diels Alder Reaction ◽

Electron Withdrawing Group

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ChemInform Abstract: Diels-Alder Reaction of 1,3-Butadiene Derivatives with 1-Methyl-2(1H)-quinolones Having an Electron-Withdrawing Group at the 4-Position.

ChemInform ◽

10.1002/chin.200152140 ◽

2010 ◽

Vol 32 (52) ◽

pp. no-no

Author(s):

Reiko Fujita ◽

Kazuhiro Watanabe ◽

Toshiteru Yoshisuji ◽

Hiroshi Hongo ◽

Hisao Matsuzaki

Keyword(s):

Alder Reaction ◽

Diels Alder ◽

Diels Alder Reaction ◽

Electron Withdrawing Group

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Diels-Alder Reactions of Cyclopentadiene with Several Ferrocenyl- and η6-Phenyltricarbonylchromium Analogues of Chalcone. Catalytic Effect of SiO2

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19960364 ◽

1996 ◽

Vol 61 (3) ◽

pp. 364-370 ◽

Cited By ~ 4

Author(s):

Monika Prokešová ◽

Grety Rihs ◽

Štefan Toma

Keyword(s):

Good Yield ◽

Room Temperature ◽

Catalytic Effect ◽

Alder Reaction ◽

Diels Alder ◽

Nmr Spectrum ◽

X Ray ◽

H Nmr ◽

Diels Alder Reaction ◽

Electron Withdrawing Group

The Diels-Alder reaction of cyclopentadiene with eight electron deficient dienophiles was studied. The reaction was performed at room temperature using silica gel as an inorganic support, without solvent. Only one of the two possible Diels-Alder adducts was isolated in moderate to good yield. The structure of products with endo-oriented electron-withdrawing group was proved by 1H NMR spectrum and in one case (9b) by X-ray analysis.

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5-Substituted-2-furoic acids as latent dienes for the preparation of aryl ethers and thioethers via the Diels-Alder reaction

The Journal of Organic Chemistry ◽

10.1021/jo00244a048 ◽

1988 ◽

Vol 53 (9) ◽

pp. 2099-2103 ◽

Cited By ~ 9

Author(s):

James A. Cella

Keyword(s):

Alder Reaction ◽

Diels Alder ◽

Diels Alder Reaction ◽

Aryl Ethers ◽

Furoic Acids

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Diels–Alder adducts of ortho-benzoquinones: rearrangements and further transformations

Canadian Journal of Chemistry ◽

10.1139/v97-097 ◽

1997 ◽

Vol 75 (6) ◽

pp. 805-816 ◽

Cited By ~ 5

Author(s):

Rina Carlini ◽

Kerianne Higgs ◽

Nicholas Taylor ◽

Russell Rodrigo

Keyword(s):

Double Bond ◽

Cycloaddition Reaction ◽

Alder Reaction ◽

Diels Alder ◽

Hydroxyl Group ◽

Carbonyl Groups ◽

Diels Alder Reaction ◽

Electron Withdrawing Group ◽

Alcoholic Hydroxyl

ortho-Benzoquinones substituted with an electron-withdrawing group (EWG = CO2Me, COSMe, COCH3, CHO) at C-3 or C-4 react as dienophiles at the C3—C4 double bond in Diels–Alder reactions with several dienes, with predictable regiochemistry. The adducts undergo migration of the "angular" EWG substituent with concomitant aromatization to produce substituted catechols. The bicyclic products can be oxidized in situ and annelated by a further Diels–Alder reaction to yield 9,10-phenanthraquinone systems. When (2E)-2,4-pentadienol is employed as the diene in the second cycloaddition, reaction of the alcoholic hydroxyl group with one of the quinone carbonyl groups results in the production of tetracyclic lactols 22a, 22b, and 23. Keywords: benzoquinone, Diels–Alder, rearrangement, phenanthraquinone, phenanthrofuran.

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