Metal-Free Decarboxylative Hetero-Diels–Alder Synthesis of 3-Hydroxypyridines: A Rapid Access to N-Fused Bicyclic Hydroxypiperidine Scaffolds

2014 ◽  
Vol 79 (3) ◽  
pp. 1303-1319 ◽  
Author(s):  
Laurie-Anne Jouanno ◽  
Vincent Di Mascio ◽  
Vincent Tognetti ◽  
Laurent Joubert ◽  
Cyrille Sabot ◽  
...  
Keyword(s):  
Diels Alder ◽  
Metal Free ◽  
Rapid Access

ChemInform Abstract: Metal-Free Decarboxylative Hetero-Diels-Alder Synthesis of 3-Hydroxypyridines: A Rapid Access to N-Fused Bicyclic Hydroxypiperidine Scaffolds.

ChemInform ◽  
2014 ◽  
Vol 45 (29) ◽  
pp. no-no
Author(s):  
Laurie-Anne Jouanno ◽  
Vincent Di Mascio ◽  
Vincent Tognetti ◽  
Laurent Joubert ◽  
Cyrille Sabot ◽  
...  
Keyword(s):  
Diels Alder ◽  
Metal Free ◽  
Rapid Access

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 One-Pot and Metal-Free Synthesis of 3-Arylated 4-Nitrophenols via Polyfunctionalized Cyclohexanones from β-Nitrostyrenes

2020 ◽  
Author(s):  
Haruyasu Asahara ◽  
Minami Hiraishi ◽  
Nagatoshi Nishiwaki
Keyword(s):  
Dimethyl Sulfoxide ◽  
Catalytic Amount ◽  
Alder Reaction ◽  
Diels Alder ◽  
One Pot ◽  
Metal Free ◽  
Diels Alder Reaction ◽  
Thienyl Group ◽  
Danishefsky's Diene

β-Nitrostyrenes underwent the Diels-Alder reaction with Danishefsky’s diene to afford cyclohexenes together with the corresponding hydrolyzed products, 3-arylated 5-methoxy-4-nitrocyclohexanones. When the reaction was conducted in the presence of water, the cyclohexenes were efficiently hydrolyzed into cyclohexanones. Subsequent aromatization by heating the cyclohexanone with a catalytic amount of iodine in dimethyl sulfoxide gave 3-arylated 4-nitrophenols. The reaction of nitrostyrenes with Danishefsky’s diene could be conducted in one-pot to directly afford the corresponding nitrophenols. Moreover, a heteroaryl group such as a thienyl group could be introduced into the nitrophenol framework.

Metal-free activation of C–C multiple bonds through halide ion pairs: Diels–Alder reactions with subsequent aromatization

2008 ◽  
Vol 49 (29-30) ◽  
pp. 4546-4549 ◽  
Author(s):  
Helena Kaper ◽  
Markus Antonietti ◽  
Frédéric Goettmann
Keyword(s):  
Ion Pairs ◽  
Diels Alder ◽  
Multiple Bonds ◽  
Metal Free

Synthesis of Tetrahydroisoindolinones via a Metal‐Free Dehydrogenative Diels‐Alder Reaction

2019 ◽  
Vol 361 (10) ◽  
pp. 2268-2273 ◽  
Author(s):  
Wen‐Lei Xu ◽  
Lei Tang ◽  
Chen‐Yu Ge ◽  
Jie Chen ◽  
Ling Zhou
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Metal Free ◽  
Diels Alder Reaction
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