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.

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.

Optically Pure Aminopolyols and Polyoxamic Acid Derivatives from Aziridine-2-carboxylates

1999 ◽  
Vol 52 (4) ◽  
pp. 259 ◽  
Author(s):  
Heribert Dollt ◽  
Volker Zabel
Keyword(s):  
Solvent Effects ◽  
Michael Addition ◽  
Building Blocks ◽  
Bulky Substituent ◽  
Cis And Trans ◽  
Optically Pure ◽  
The Michael Addition

Various new chiral building blocks could easily be prepared from optically pure cis and trans ethyl 3-(1′,3′- dioxolan-4′-yl)aziridine-2-carboxylates. A stereochemically pure 1,3-dioxolan in the allyl position of an α-bromoacrylate induced a high (3R*,4′S*) selectivity in the Michael addition with an amine. After oxygen at the inducing centre was exchanged with nitrogen bearing a bulky substituent, the directing influence of this new group was examined. Solvent effects influencing the cis/trans ratio of aziridine formation are discussed.

scholarly journals Synthesis and evaluation of new guanidine-thiourea organocatalyst for the nitro-Michael reaction: Theoretical studies on mechanism and enantioselectivity

2012 ◽  
Vol 8 ◽  
pp. 1485-1498 ◽  
Author(s):  
Tatyana E Shubina ◽  
Matthias Freund ◽  
Sebastian Schenker ◽  
Timothy Clark ◽  
Svetlana B Tsogoeva
Keyword(s):  
Reaction Mechanism ◽  
Dft Calculations ◽  
Solvent Effects ◽  
Michael Addition ◽  
Michael Reaction ◽  
Addition Reaction ◽  
Diethyl Malonate ◽  
Theoretical Studies ◽  
Michael Addition Reaction ◽  
The Michael Addition

A new guanidine-thiourea organocatalyst has been developed and applied as bifunctional organocatalyst in the Michael addition reaction of diethyl malonate to trans-β-nitrostyrene. Extensive DFT calculations, including solvent effects and dispersion corrections, as well as ab initio calculations provide a plausible description of the reaction mechanism.

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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