Recent Advances in Chemistry and Biological Activity of 2,6-Diphenyl piperidines

2021 ◽  
Vol 18 ◽  
Author(s):  
Mahmoud N. M. Yousif
Keyword(s):  
Biological Activity ◽  
Nitrogen Atom ◽  
Aromatic Aldehyde ◽  
Ammonium Acetate ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Function Group ◽  
Methylene Group ◽  
Carbonyl Function

: The review discusses different methods for preparation of 2,6-diphenyl-piperidin-4-one derivatives. 2,6-Diphenyl-piperidin-4-one is prepared from aromatic aldehyde and acetone in ammonium acetate. Reaction of 1-phenylsulfinylpropan-2-one or 1-(4-chlorophenylsulfinyl)propan-2-one, aromatic aldehyde and ammonium acetate gives a series of 2,6-diaryl-2,3-dihydro-1H-pyridin-4-one 6a,b. 4-Phenyl-2-amino-1,3-butadienes reacts with N-allyl benzaldimine through Diels-Alder reaction to afford 2,6-diphenyl-4-piperidinone derivative 7. Also, reactions of 2,6-diphenyl-piperdin-4-one are discussed. The reactions of latter compounds can be on nitrogen atom or carbonyl function group or methylene group adjacent to carbonyl group. In addition, different applications of 2,6-diphenyl-piperidin-4-one are summarized.

Novel Synthesis of Heterocyclic Compounds Having Angular Nitrogen Atom by Intramolecular Diels-Alder Reaction of 1-1-Azadienes

Heterocycles ◽  
1985 ◽  
Vol 23 (1) ◽  
pp. 221 ◽  
Author(s):  
Tetsuji Kametani ◽  
Masataka Ihara ◽  
Akihiro Kawaguchi ◽  
Tomoko Kirihara ◽  
Keiichiro Fukumoto
Keyword(s):  
Nitrogen Atom ◽  
Heterocyclic Compounds ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Novel Synthesis

Quantum-chemical investigation of the Diels-Alder reaction in condensed isoindoles with a nodal nitrogen atom

1988 ◽  
Vol 24 (2) ◽  
pp. 179-185
Author(s):  
V. A. Kovtunenko ◽  
Z. V. Voitenko ◽  
L. I. Savranskii ◽  
A. K. Tyltin ◽  
F. S. Babichev
Keyword(s):  
Nitrogen Atom ◽  
Quantum Chemical ◽  
Alder Reaction ◽  
Diels Alder ◽  
Chemical Investigation ◽  
Quantum Chemical Investigation ◽  
Diels Alder Reaction

Application of the aza-Diels–Alder reaction in the synthesis of natural products

2017 ◽  
Vol 15 (15) ◽  
pp. 3105-3129 ◽  
Author(s):  
Min-Hui Cao ◽  
Nicholas J. Green ◽  
Sheng-Zhen Xu
Keyword(s):  
Natural Products ◽  
Nitrogen Atom ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction

The Diels–Alder reaction that involves a nitrogen atom in the diene or dienophile is termed the aza-Diels–Alder reaction.

scholarly journals Chiral pyrrolidinium salts derived from menthol as precursor – synthesis and properties

2017 ◽  
Vol 19 (3) ◽  
pp. 92-98 ◽  
Author(s):  
Ewa Janus ◽  
Marcin Gano
Keyword(s):  
Nitrogen Atom ◽  
Room Temperature ◽  
Alder Reaction ◽  
Diels Alder ◽  
Quaternary Nitrogen ◽  
Quaternary Nitrogen Atom ◽  
Diels Alder Reaction ◽  
Precursor Synthesis ◽  
Chiral Ionic Liquid ◽  
Anion Type

Abstract Six new chiral pyrolidinium salts with chiral substituent at quaternary nitrogen atom were synthesized with high overall yields from (-)-menthol as cheap chiral precursor and were identified by NMR and HRMS spectroscopy. It was shown that anion type had the effect on chemical shift of protons adjacent to quaternary nitrogen atom and physical properties of these salts. Salts with NTf2 or NPf2 were in a liquid state at room temperature and characterized with the highest thermal stability among others. Furthermore, chiral ionic liquid with NTf2 anion was used as solvent in Diels-Alder reaction and gave higher yield and stereoselectivity than in ionic liquids with achiral cations. Synthesized chiral salts have the potential as chiral solvents in synthesis and auxiliaries in analytical methods to improve chiral recognition.

Organic Sulfur Mechanisms. 13. Sulfene Formation by a Reverse Diels–Alder Reaction

1973 ◽  
Vol 51 (18) ◽  
pp. 3044-3050 ◽  
Author(s):  
James Frederick King ◽  
Errol George Lewars
Keyword(s):  
Sulphur Dioxide ◽  
Alder Reaction ◽  
Diels Alder ◽  
Organic Sulfur ◽  
Diels Alder Reaction ◽  
Methylene Group

Dimethyl 2,2-dioxido-4-phenyl-2-thiabicyclo[2.2.2]octa-5,7-diene-5,6-dicarboxylate (5), a molecule purposely designed to undergo a thermal reverse Diels–Alder reaction to form sulfene and an aromatic co-fragment, has been synthesized. Thermolysis of 5 gave dimethyl biphenyl-2,3-dicarboxylate (7) and, in addition, (a) in the presence of an enamine (6) gave the appropriate sulfene–enamine adduct (8), and (b) with an excess of p-toluidine gave methanesulfon-p-toluidide (10), in agreement with the above expectation. In the absence of sulfene traps the only product identified, in addition to 7, was sulphur dioxide; further experiments failed to determine the fate of the methylene group but serve to exclude certain possibilities, including fragmentation of sulfene to sulphur dioxide and a trappable carbenoid species.

The Diels-Alder Reaction of 2-Ethenyl-1,4-Benzodioxin: A New and Simple Synthesis of Bisaryl Ethers

Synlett ◽  
1989 ◽  
Vol 1989 (01) ◽  
pp. 30-32
Author(s):  
Thomas V. Lee ◽  
Alistair J. Leigh ◽  
Christopher B. Chapleo
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Simple Synthesis ◽  
Diels Alder Reaction
Sign in / Sign up

Export Citation Format

Share Document