Toward design of a practical methodology for stereocontrolled synthesis of χ-constrained pyroglutamic acids and related compounds. Virtually complete control of simple diastereoselectivity in the Michael addition reactions of glycine Ni(II) complexes with N-(enoyl)oxazolidinones

2000 ◽  
Vol 41 (2) ◽  
pp. 135-139 ◽  
Author(s):  
Vadim A Soloshonok ◽  
Chaozhong Cai ◽  
Victor J Hruby
Keyword(s):  
Michael Addition ◽  
Addition Reactions ◽  
Complete Control ◽  
Stereocontrolled Synthesis ◽  
Related Compounds ◽  
The Michael Addition

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.

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.

Theoretical studies on the activation mechanism involving bifunctional tertiary amine–thioureas and isatylidene malononitriles

RSC Advances ◽  
2015 ◽  
Vol 5 (43) ◽  
pp. 34314-34318 ◽  
Author(s):  
Zheng-Hang Qi ◽  
Ye Zhang ◽  
Gui-Yu Ruan ◽  
Yi Zhang ◽  
Yong Wang ◽  
...  
Keyword(s):  
Tertiary Amine ◽  
Michael Addition ◽  
Activation Mechanism ◽  
Addition Reactions ◽  
Theoretical Studies ◽  
Dft Studies ◽  
The Michael Addition

DFT studies on the activation mechanism of the Michael addition reactions containing bifunctional tertiary amine–thioureas and isatylidene malononitriles have been performed at the B3LYP/6-311++G(d,p)//B3LYP/6-31G(d) level of theory.

Curve crossing analysis of LFER data in Michael addition reactions

1992 ◽  
Vol 70 (4) ◽  
pp. 1022-1027 ◽  
Author(s):  
Zeev Gross ◽  
Shmaryahu Hoz
Keyword(s):  
Chemical Shift ◽  
Transition State ◽  
Michael Addition ◽  
Electronic Configuration ◽  
Nucleophilic Attack ◽  
Addition Reactions ◽  
Rate Correlation ◽  
The Michael Addition ◽  
Curve Crossing

Rate constants for the Michael addition of CN− in water, aqueous sulfolane, and DMSO, and MeO− in MeOH to eight mono- and disubstituted 1,1-diaryl-2,2-dinitroethylenes were measured. The ρ values are in the range 0.7 (CN−/H2O) –1.6 (MeO−/MeOH). For each of the four systems a correlation was found between log k and the 13C chemical shift of the carbon that undergoes the nucleophilic attack. However, the quality of the correlation as well as the slope decreases with decreasing ρ values. Analysis of the electronic configuration of the transition state using the curve crossing model shows that the traditional interpretation of the location of the transition state should be reversed. This analysis provides a rationale for the observed dependence of the chemical shift – rate correlation on the ρ value.

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.

A stereocontrolled synthesis of Hagen's gland lactones via iterative proline catalyzed α-aminoxylation and oxa-Michael addition reactions

RSC Advances ◽  
2015 ◽  
Vol 5 (75) ◽  
pp. 61000-61005 ◽  
Author(s):  
Shruti Vandana Kauloorkar ◽  
Vishwajeet Jha ◽  
Ganesh Jogdand ◽  
Pradeep Kumar
Keyword(s):  
Michael Addition ◽  
Addition Reactions ◽  
Efficient Synthesis ◽  
Stereocontrolled Synthesis

A simple and efficient synthesis of Hagen's gland lactones was achieved using a sequential α-aminoxylation/oxa-Michael approach in a highly diastereoselective manner with assignment of relative configurations.

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