scholarly journals Asymmetric Synthesis of (+)-Phosphinothricin and Related Compounds by the Michael Addition of Glycine Schiff Bases to Vinyl Compounds

1987 ◽  
Vol 60 (5) ◽  
pp. 1761-1766 ◽  
Author(s):  
Nobuto Minowa ◽  
Masao Hirayama ◽  
Shunzo Fukatsu
Keyword(s):  
Asymmetric Synthesis ◽  
Schiff Bases ◽  
Michael Addition ◽  
Related Compounds ◽  
The Michael Addition

Synthesis of biologically active heterocyclic compounds from allenic and acetylenic nitriles and related compounds

2021 ◽  
Vol 0 (0) ◽  
Author(s):  
Marthe Carine Djuidje Fotsing ◽  
Dieudonné Njamen ◽  
Zacharias Tanee Fomum ◽  
Derek Tantoh Ndinteh
Keyword(s):  
Michael Addition ◽  
Heterocyclic Compounds ◽  
Biological Activities ◽  
Biologically Active ◽  
Polycyclic Compounds ◽  
One Step ◽  
Pharmaceutical Properties ◽  
Related Compounds ◽  
Acetylenic Acids ◽  
The Michael Addition

Abstract Cyclic and polycyclic compounds containing moieties such as imidazole, pyrazole, isoxazole, thiazoline, oxazine, indole, benzothiazole and benzoxazole benzimidazole are prized molecules because of the various pharmaceutical properties that they display. This led Prof. Landor and co-workers to engage in the synthesis of several of them such as alkylimidazolenes, oxazolines, thiazolines, pyrimidopyrimidines, pyridylpyrazoles, benzoxazines, quinolines, pyrimidobenzimidazoles and pyrimidobenzothiazolones. This review covers the synthesis of biologically active heterocyclic compounds by the Michael addition and the double Michael addition of various amines and diamines on allenic nitriles, acetylenic nitriles, hydroxyacetylenic nitriles, acetylenic acids and acetylenic aldehydes. The heterocycles were obtained in one step reaction and in most cases, did not give side products. A brief discussion on the biological activities of some heterocycles is also provided.

scholarly journals Diastereoselective Cyclopropanation by Using Camphorpyrazolidinone Derived α,β-Unsaturated Amides and Ylide

2020 ◽  
Author(s):  
sudershan gondi
Keyword(s):  
Carboxylic Acid ◽  
Asymmetric Synthesis ◽  
Michael Addition ◽  
Chemical Yield ◽  
High Chemical ◽  
Unsaturated Carboxylic Acid ◽  
Optically Pure ◽  
The Michael Addition

<p><b>Abstract:</b> High to moderate diastereoselectivity and high chemical yield are observed in the Michael addition of ylide and chiral camphorpyrazolidinone ylide to an optically pure a,b-unsaturated carboxylic acid derivatives derived from a chiral camphorpyrazolidinone and a,b-unsaturated carbonyl respectively. A novel route to the asymmetric synthesis of cyclopropanation derivatives is described.</p>

Economical Synthesis of α-Amino Acids from a Novel Family of Easily Available Schiff Bases of Glycine Esters and 2-Hydroxy­benzophenone

Synthesis ◽  
2017 ◽  
Vol 50 (03) ◽  
pp. 607-616 ◽  
Author(s):  
Yuri Belokon ◽  
Zalina Gugkaeva ◽  
Vladimir Larionov ◽  
Margarita Moskalenko ◽  
Victor Khrustalev ◽  
...  
Keyword(s):  
Amino Acids ◽  
Schiff Bases ◽  
Methyl Acrylate ◽  
Michael Addition ◽  
Alkylation Reaction ◽  
Different Types ◽  
The Michael Addition

We report a novel, efficient, and easily prepared substrate/precursor family of Schiff bases of various glycine esters with 2-hydroxybenzophenone, and their use for the synthesis of amino acids in quantitative yields. The Michael addition of the substrates to methyl acrylate gave two different types of product (cyclic or chain), depending on the nature of the base. Also, we demonstrated that one of the new substrates could be involved in an asymmetric version of the alkylation reaction (70% ee).

TRYPTAMINES, CARBOLINES, AND RELATED COMPOUNDS: PART VI. STEREOCHEMISTRY OF THE MICHAEL ADDITION OF ETHYL MALONATE TO 1-CYCLOHEXENE CYANIDE

1960 ◽  
Vol 38 (4) ◽  
pp. 557-566 ◽  
Author(s):  
R. A. Abramovitch ◽  
J. M. Muchowski
Keyword(s):  
Michael Addition ◽  
Diethyl Malonate ◽  
Aminomethyl Derivative ◽  
Fischer Cyclization ◽  
Ethyl Malonate ◽  
Cis And Trans ◽  
Related Compounds ◽  
The Michael Addition

The Michael addition of diethyl malonate to 1-cyclohexene cyanide has been shown to give a mixture of the cis- and trans-diethyl 2-cyanocyclohexylmalonates in 72% and 28% yields respectively. The stereochemistry of the products was established by their unambiguous conversion to the respective cis- and trans-decahydroisoquinolines. Hydrogenation of a cyclohexane cyanide to the corresponding aminomethyl derivative takes place with retention of configuration. A number of substituted decahydroisoquinolines of known stereochemistry have been prepared. Decahydro-3,4-dioxoisoquinoline-4-phenylhydrazone underwent Fischer cyclization to a product assumed to be 2-oxo-octahydroindolo[2,3-d]isoquinoline indicating that the observation that 4-methyl-2,3-dioxopiperidine-3-phenylhydrazone did not undergo cyclization is not general for such 4-substituted piperidones.

Carcinogenicity of lactones. IV. Alkylation of analogues of DNA guanine groups such as imidazole, N-methylimidazole, and guanosine by α, β-unsaturated acids

1970 ◽  
Vol 48 (10) ◽  
pp. 1566-1573 ◽  
Author(s):  
J. Bryan Jones ◽  
John M. Young
Keyword(s):  
Michael Addition ◽  
Alkylating Agents ◽  
Addition Reactions ◽  
Hydrolysis Of ◽  
Related Compounds ◽  
The Michael Addition

Studies on the reactions of carcinogenic γ-lactones and related compounds with analogues of guanine DNA residues indicate that the lactones themselves will not effect permanent alkylation of the guanine N-7 position since the Michael addition reactions involved would be readily reversible. In contrast, the α,β-unsaturated acids resulting from hydrolysis of such lactones are effective guanine N-7 alkylating agents owing to zwitterionic stabilization of the corresponding Michael addition products.

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