Dehydrogenation/Diels-Alder Cycloaddition Domino Reaction of 9,10-Dihydroanthracene with N-Substituted Maleimides Triggered by the Application of Activated Carbon

2014 ◽  
Vol 18 (11) ◽  
pp. 1520-1527 ◽  
Author(s):  
Marko Krivec ◽  
Kristof Kranjc ◽  
Slovenko Polanc ◽  
Marijan Kocevar
Keyword(s):  
Activated Carbon ◽  
Diels Alder ◽  
Domino Reaction

scholarly journals Metal-Free Four-Step Domino Reaction Enables Fully Controlled Non-Statistical Synthesis of Hexaarylbenzene with Six Different Aryl Groups

2021 ◽  
Author(s):  
Benedikt Grau ◽  
Maximilian Dill ◽  
Frank Hampel ◽  
Axel Kahnt ◽  
Norbert Jux ◽  
...  
Keyword(s):  
Liquid Crystalline ◽  
Diels Alder ◽  
Domino Reaction ◽  
Aromatic Rings ◽  
Light Emitting ◽  
Crystalline Materials ◽  
Metal Free ◽  
Synthetic Strategy ◽  
Starting Compound ◽  
Liquid Crystalline Materials

Hexaarylbenzene (HAB) derivatives are versatile aromatic systems playing a significant role as chromophores, liquid crystalline materials, molecular receptors, redox materials, organic light-emitting diodes and photochemical switches. Statistical synthesis of simple symmetrical HABs is known <i>via</i> low-yielding cyclotrimerization or Diels-Alder reactions. By contrast, the synthesis of more complex, asymmetrical systems, and without involvement of statistical steps, remains an unsolved problem. Here we present a generally applicable synthetic strategy to access asymmetrical HAB <i>via</i> an atom-economical and high-yielding metal-free four-step domino reaction using nitrostyrenes and <i>α,α</i>-dicyanoolefins as easily available starting materials. Resulting domino product – functionalized triarylbenzene (TAB) - can be used as a key starting compound to furnish asymmetrically substituted hexaarylbenzenes in high overall yield and without involvement of statistical steps. This straightforward domino process represents a distinct approach to creating diverse and still unexplored HAB scaffolds, containing six different aromatic rings around central benzene core.

Thiazolidine-2,4-dithione in the Knoevenagel/Hetero Diels–Alder Domino Reaction

2020 ◽  
Vol 56 (8) ◽  
pp. 1495-1497
Author(s):  
Y. V. Ostapiuk ◽  
T. I. Chaban ◽  
V. S. Matiychuk
Keyword(s):  
Diels Alder ◽  
Domino Reaction

scholarly journals A Merged Aldol Condensation, Alkene Isomerization, Cycloaddition/Cycloreversion Sequence Employing Oxazinone Intermediates for the Synthesis of Substituted Pyridines

Synlett ◽  
2017 ◽  
Vol 28 (10) ◽  
pp. 1170-1172 ◽  
Author(s):  
Jonathan Scheerer ◽  
Jill Williamson ◽  
Emily Smith
Keyword(s):  
Aldol Condensation ◽  
Reaction Vessel ◽  
Diels Alder ◽  
Domino Reaction ◽  
Reaction Sequence ◽  
Alkene Isomerization ◽  
Substituted Pyridines

A domino reaction sequence has been evaluated that begins with union of novel dihydrooxazinone precursors with 2-alkynyl-substituted benzaldehyde components through aldol condensation. Ensuing operations, including alkene isomerization, Diels–Alder, and retrograde Diels–Alder with loss of CO2 occurs in the same reaction vessel to provide polysubstituted tricyclic pyridine products.

scholarly journals Metal-Free Four-Step Domino Reaction Enables Fully Controlled Non-Statistical Synthesis of Hexaarylbenzene with Six Different Aryl Groups

2021 ◽  
Author(s):  
Benedikt Grau ◽  
Maximilian Dill ◽  
Frank Hampel ◽  
Axel Kahnt ◽  
Norbert Jux ◽  
...  
Keyword(s):  
Liquid Crystalline ◽  
Diels Alder ◽  
Domino Reaction ◽  
Aromatic Rings ◽  
Light Emitting ◽  
Crystalline Materials ◽  
Metal Free ◽  
Synthetic Strategy ◽  
Starting Compound ◽  
Liquid Crystalline Materials

Hexaarylbenzene (HAB) derivatives are versatile aromatic systems playing a significant role as chromophores, liquid crystalline materials, molecular receptors, redox materials, organic light-emitting diodes and photochemical switches. Statistical synthesis of simple symmetrical HABs is known <i>via</i> low-yielding cyclotrimerization or Diels-Alder reactions. By contrast, the synthesis of more complex, asymmetrical systems, and without involvement of statistical steps, remains an unsolved problem. Here we present a generally applicable synthetic strategy to access asymmetrical HAB <i>via</i> an atom-economical and high-yielding metal-free four-step domino reaction using nitrostyrenes and <i>α,α</i>-dicyanoolefins as easily available starting materials. Resulting domino product – functionalized triarylbenzene (TAB) - can be used as a key starting compound to furnish asymmetrically substituted hexaarylbenzenes in high overall yield and without involvement of statistical steps. This straightforward domino process represents a distinct approach to creating diverse and still unexplored HAB scaffolds, containing six different aromatic rings around central benzene core.

scholarly journals Gold(I)-Catalyzed Domino Reaction for Furopyrans Synthesis

Molecules ◽  
2020 ◽  
Vol 25 (21) ◽  
pp. 4976
Author(s):  
Marie Ruch ◽  
Nicolas Brach ◽  
Roméric Galéa ◽  
Patrick Wagner ◽  
Gaëlle Blond
Keyword(s):  
Cascade Reaction ◽  
Diels Alder ◽  
Domino Reaction ◽  
Efficient Synthesis ◽  
One Pot ◽  
Quaternary Center ◽  
Stereogenic Centers

We report herein an efficient synthesis of furopyran derivatives through a gold(I)-catalyzed domino reaction. The cascade reaction starts with two regioselective cyclizations, a 5-endo-dig and a 8-endo-dig, followed with a Grob-type fragmentation and a hetero Diels–Alder. The obtained furopyran derivatives contain fused and spiro-heterocycles. During this one-pot process, four bonds and four controlled stereogenic centers including a quaternary center are formed.

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