scholarly journals Oxidative Asymmetric Formal Aza-Diels–Alder Reactions of Tetrahydro-β-carboline with Enones in the Synthesis of Indoloquinolizidine-2-ones

Molecules ◽  
2018 ◽  
Vol 23 (9) ◽  
pp. 2228 ◽  
Author(s):  
Xiang Wu ◽  
Shi-Bao Zhao ◽  
Lang-Lang Zheng ◽  
You-Gui Li
Keyword(s):  
Oxidative Dehydrogenation ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diastereoselective Synthesis ◽  
Butyl Hydroperoxide ◽  
Unsaturated Ketones ◽  
Tert Butyl ◽  
Diels Alder Reaction ◽  
Tert Butyl Hydroperoxide ◽  
Reaction Proceeds

Ru-catalyzed tandem amine oxidative dehydrogenation/formal aza-Diels–Alder reaction for enantio- and diastereoselective synthesis of indoloquinolizidine-2-ones from tetrahydro-β-carbolines and α,β-unsaturated ketones is described. The reaction proceeds via tandem ruthenium-catalyzed amine dehydrogenation using tert-butyl hydroperoxide (TBHP) as the oxidant and a chiral thiourea-catalyzed formal aza-[4 + 2] cycloaddition, providing a step-economical strategy for the synthesis of these valuable heterocyclic products.

A synthesis and some reactions of 7-Oxabicyclo[2.2.1]heptan-2-one

1983 ◽  
Vol 36 (12) ◽  
pp. 2473 ◽  
Author(s):  
J Moursounidis ◽  
D Wege
Keyword(s):  
Thermal Decomposition ◽  
Alder Reaction ◽  
Diels Alder ◽  
Acid Mixture ◽  
Diels Alder Reaction ◽  
Reaction Proceeds ◽  
Atom Migration ◽  
Acyl Azide ◽  
Mild Hydrolysis ◽  
Hydrolysis Of

Diels-Alder reaction between furan and α-chloroacrylonitrile gives a mixture of exo-2-chloro-and endo-2-chloro-7-oxabicyclo[2.2.1]hept-5-ene-2-carbonitrile (4) and (5). Mild hydrolysis affords the corresponding α-chloro acid mixture, from which the endo carboxylic acid may be removed through iodo lactone formation. Catalytic hydrogenation of (4) and (5) followed by hydrolysis, acyl azide formation, Curtius rearrangement, and hydrolysis of the resulting mixture of a-chloro isocyanates yields 7-oxabicyclo[2.2.l]heptan-2-one (1) in preparatively useful amounts. Reduction of (1) gives only endo alcohol, and Baeyer-Villiger reaction proceeds with exclusive bridgehead atom migration. Thermal decomposition of the sodium salt of the p-toluenesulfonylhydrazone of (1) affords 7-oxatricyclo[2.2.1 .02,6]heptane.

scholarly journals Diastereoselective synthesis of novel spiro indanone fused pyrano[3,2-c]chromene derivatives following hetero-Diels–Alder reaction andin vitroanticancer studies

RSC Advances ◽  
2018 ◽  
Vol 8 (30) ◽  
pp. 16802-16814 ◽  
Author(s):  
Pravati Panda ◽  
Sabita Nayak ◽  
Susanta Ku. Sahoo ◽  
Seetaram Mohapatra ◽  
Deepika Nayak ◽  
...  
Keyword(s):  
Anticancer Activity ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diastereoselective Synthesis ◽  
Diels Alder Reaction

Synthesis of novel spiro indanone fused pyrano[3,2-c]chromene derivatives following hetero-Diels–Alder reaction has been demonstrated and evaluated for theirin vitroanticancer activity.

ChemInform Abstract: Organocatalytic Oxa-Diels-Alder Reaction of α,β-Unsaturated Ketones under Non-Classical Conditions.

ChemInform ◽  
2015 ◽  
Vol 46 (32) ◽  
pp. no-no
Author(s):  
Melinda Mojzesova ◽  
Maria Meciarova ◽  
Roger Marti ◽  
Radovan Sebesta
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Unsaturated Ketones ◽  
Diels Alder Reaction

A Flow Microreactor Approach to a Highly Efficient Diels–Alder Reaction with an Electrogenerated o-Quinone

Synlett ◽  
2019 ◽  
Vol 30 (10) ◽  
pp. 1194-1198 ◽  
Author(s):  
Kenta Tanaka ◽  
Hirona Yoshizawa ◽  
Mahito Atobe
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Tert Butyl ◽  
Highly Efficient ◽  
Diels Alder Reaction ◽  
Flow Microreactor ◽  
Chemical Oxidants

We have demonstrated a Diels–Alder reaction of an o-quinone generated in an electrochemical flow microreactor. In the flow microreactor system, 4-tert-butyl-o-benzoquinone was easily electrogenerated from 4-tert-butylpyrocatechol in the absence of chemical oxidants and then rapidly used, without decomposing, in a subsequent Diels–Adler reaction with various fulvenes to give the desired products efficiently.

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