Liquid-phase synthesis of 2,3-dihydro-4-pyridones: one-pot three-component aza Diels–Alder reaction of Danishefsky's diene with aldehydes and PEG-supported amine

2003 ◽  
Vol 44 (37) ◽  
pp. 7103-7106 ◽  
Author(s):  
Hongchao Guo ◽  
Kuiling Ding
Keyword(s):  
Liquid Phase ◽  
Alder Reaction ◽  
Diels Alder ◽  
One Pot ◽  
Phase Synthesis ◽  
Diels Alder Reaction ◽  
Danishefsky's Diene

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.

scholarly journals One-pot and metal-free synthesis of 3-arylated-4-nitrophenols via polyfunctionalized cyclohexanones from β-nitrostyrenes

2020 ◽  
Vol 16 ◽  
pp. 1830-1836
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 a 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, e.g., a thienyl group could be introduced into the nitrophenol framework.

Solid-Phase Organic Synthesis of Dexoxadrol Analogues

2013 ◽  
Vol 66 (1) ◽  
pp. 93 ◽  
Author(s):  
Michael Sax ◽  
Bernhard Wünsch
Keyword(s):  
Solid Phase ◽  
Alder Reaction ◽  
Solid Support ◽  
Diels Alder ◽  
Piperidine Ring ◽  
Phase Synthesis ◽  
Diels Alder Reaction ◽  
Conjugate Reduction ◽  
Solid Phase Organic Synthesis ◽  
Danishefsky's Diene

A solid-phase synthesis of dexoxadrol analogues like-13 and unlike-13 bearing an oxo group in the 4-position of the piperidine ring has been developed using aminomethyl substituted polystyrene resin as solid support. The synthesis comprises a hetero-Diels–Alder reaction of imine 7b with Danishefsky’s diene 8 in the presence of the Lewis acid Yb(OTf)3 and a conjugate reduction of the double bond of 9b with LiBHEt3 and BF3. The cleavage of the product from the solid support was performed with 1-chloroethyl chloroformate. All transformations on the solid support and additionally the cleavage reaction had to be compatible with the large and acid labile acetalic 1,3-dioxolane moiety in 2-position of the piperidine ring. The oxodexoxadrol derivative 12 was obtained in an overall yield of 17 %.

Aza-Diels-Alder Reaction Between 1,2-Diaza-1,3-dienes and β-Aryl-α,β-unsaturated Carbonyl Compounds. Easy One-pot Entry to 2’-Oxo-imidazo[1’,5’- f]tetrahydropyridazine

2014 ◽  
Vol 10 (6) ◽  
pp. 951-960
Author(s):  
Orazio Attanasi ◽  
Luca Bianchi ◽  
Maurizio D’Auria ◽  
Gianfranco Favi ◽  
Fabio Mantellini ◽  
...  
Keyword(s):  
Carbonyl Compounds ◽  
Alder Reaction ◽  
Diels Alder ◽  
One Pot ◽  
Diels Alder Reaction

Enantioselective Diels–Alder Reaction of 3-Nitrocoumarins Promoted by Chiral Organoammonium Salt Catalysts

Synlett ◽  
2020 ◽  
Vol 31 (20) ◽  
pp. 2013-2017
Author(s):  
Akira Sakakura ◽  
Yudai Fujii ◽  
Ryota Nakao ◽  
Saki Sugihara ◽  
Keita Fujita ◽  
...  
Keyword(s):  
Amino Alcohol ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Danishefsky's Diene

AbstractAn enantioselective Diels–Alder reaction of 3-nitrocoumarins has been developed. A tryptophan-derived C 1-symmetric organoammonium thiourea catalyst promoted the reaction of 3-nitrocoumarins with Danishefsky’s diene to give the corresponding adducts with good enantioselectivity (up to 94% ee). One of the resulting adducts was converted into a chiral carbocyclic quaternary β-amino alcohol.

Insights into the stereoselective BF3-catalyzed hetero Diels–Alder reaction of Garner’s aldehyde with Danishefsky’s diene

2010 ◽  
Vol 21 (4) ◽  
pp. 398-404 ◽  
Author(s):  
Carolina Fontana ◽  
Marcelo Incerti ◽  
Guillermo Moyna ◽  
Eduardo Manta
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Danishefsky's Diene
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