Reactivity of triformylmethane. I. Reactions of triformylmethane with selected types of amino compounds

1991 ◽  
Vol 56 (5) ◽  
pp. 1019-1031 ◽  
Author(s):  
Zdeněk Arnold ◽  
Miloš Buděšínský ◽  
Magdalena Pánková
Keyword(s):  
Lewis Acids ◽  
Secondary Amines ◽  
Primary Amines ◽  
Carbamic Acid ◽  
Sulfonic Acids ◽  
Primary Products ◽  
Amino Compounds ◽  
Related Compounds

Reactions of triformylmethane with various types of amino compounds were investigated. Besides with ammonia, triformylmethane reacts spontaneously with primary amines, aminoacids and their esters, urea and related compounds including carbamic acid derivatives. Reactions with amides of carboxylic and sulfonic acids require catalysis with Lewis acids. Primary products are aminomethylenemalonaldehyde derivatives IIIa-IIIv. Reactions of triformylmethane with excess of selected primary amines and two secondary amines (dimethylamine and morpholine) were also studied.

Cyclic amidines derived from benz[c,d]indole and 4,5-dihydro-3H-1-benzazepine including some related compounds: Synthesis and pharmacological screening

1985 ◽  
Vol 50 (8) ◽  
pp. 1888-1898 ◽  
Author(s):  
Miroslav Protiva ◽  
Zdeněk Šedivý ◽  
Jiří Holubek ◽  
Emil Svátek ◽  
Jiří Němec
Keyword(s):  
Titanium Tetrachloride ◽  
Aqueous Sodium Hydroxide ◽  
Secondary Amines ◽  
Primary Amines ◽  
Open Chain ◽  
Lithium Aluminium ◽  
Pharmacological Screening ◽  
Antiinflammatory Effects ◽  
Related Compounds ◽  
Sodium Amide

Reactions of naphthostyril (I) with primary and secondary amines and titanium tetrachloride afforded cyclic amidines III-IX. Hydrogenation of I on Pd-C resulted in the 6,7,8,8a-tetrahydro derivative X which gave by treatment with sodium amide and 3-dimethylaminopropyl chloride the N-(aminoalkyl) compound XI. Reduction of I and its N-methyl derivative II with sodium amalgam in aqueous sodium hydroxide gave the 2a,3,4,5-tetrahydro derivatives XII and XIII. Reaction of XIII with sodium amide and 3-dimethylaminopropyl chloride afforded the 2a-(aminoalkyl) compound XIV. 1,3,4,5-Tetrahydro-1-benzazepin-2-one (XV) treated with primary amines and titanium tetrachloride gave the amidines XVI-XVIII. 3-Methyl-7,8,9,9a-tetrahydro-1H-benz[d,e]isoquinoline (XIX) was reduced with sodium borohydride to compound XX which was alkylated with propargyl bromide to 1-methyl-2-propargyl-2,3,3a,4,5,6-hexahydro-1H-benz[d,e]isoquinoline (XXI). An attempt to prepare the 2-(2-phenylethyl) analogue by treatment of compound XX with phenylacetyl chloride and by the following reduction with lithium aluminium hydride resulted in the open-chain amine XXII. The lactams I, II, X, and XIII showed some discoordinating, hypothermic, peripheral vasodilating, hyperglycaemic, diuretic and antiinflammatory effects. The amidines III-IX and XVI-XVIII had local anaesthetic, slight hypotensive, antiarrhythmic, peripheral myorelaxant, papaverine-like spasmolytic and thiopental potentiating effects.

Photochemischer Abbau N-substituierter O-Alkylurethane / The Photolysis of N-Substituted O-Alkylurethanes

1973 ◽  
Vol 28 (5-6) ◽  
pp. 339-352 ◽  
Author(s):  
Hartmut Schultze
Keyword(s):  
Benzoic Acid ◽  
Alkyl Group ◽  
Aromatic Amines ◽  
Acid Ethyl Ester ◽  
Primary Amines ◽  
Carbamic Acid ◽  
Alkyl Esters ◽  
Primary Products ◽  
Acid Esters ◽  
Amino Benzoic Acid

The photolysis of N-aryl-carbamic acid alkyl esters in methanol was investigated. The primary products, amino-benzoic acid esters and aromatic amines, result from photo-Fries rearrangements and splitting processes.2,4,6-Trimethylphenyl-carbamic acid ethyl ester and N-alkyl-carbamic acid alkyl esters form photolysis products only through homolytic splitting reactions.The photooxidation of N-substituted urethanes has been investigated in tert.-butanol. The main products are primary amines and CO2.These initially formed compounds are then further oxidized. In the aliphatic substituted derivatives, oxidation of the N-alkyl group results followed homolytic bond splitting.

scholarly journals FLUORESCENCE OF CATECHOL AMINES AND RELATED COMPOUNDS CONDENSED WITH FORMALDEHYDE

1962 ◽  
Vol 10 (3) ◽  
pp. 348-354 ◽  
Author(s):  
B. FALCK ◽  
N.-Å. HILLARP ◽  
G. THIEME ◽  
A. TORP
Keyword(s):  
Heterocyclic Ring ◽  
Secondary Reaction ◽  
Secondary Amines ◽  
Primary Amines ◽  
Hydroxyl Groups ◽  
Protein Film ◽  
Mild Conditions ◽  
Catechol Amines ◽  
Formaldehyde Vapour ◽  
Related Compounds

The reaction under mild conditions between formaldehyde and phenylalanine and phenylethylamine derivatives has been studied. When the amines included in a dried protein film were exposed to formaldehyde vapour a very intense green to yellow fluorescence was give only by those that as well as being primary amines also have hydroxyl groups at the 3 and 4 positions (3,4-dihydroxyphenylalanine, dopamine, noradrenaline). The 3-OH group seems to be esssential for the reaction. The catechol amines, which are secondary amines (adrenaline, epinine), gave a much weaker fluorescence that developed more slowly. The results obtained on further examination of the reaction favour the view that the amines primarily condense with formaldehyde to 1,2,3,4-tetrahydroisoquinolines which are involved in a secondary reaction to become highly fluorescent and at the same time insoluble. This secondary reaction may be a binding to protein, and oxidation with the formation of double bonds in the heterocyclic ring, or both.

Acceptorless amine dehydrogenation and transamination using Pd-doped layered double hydroxides

2018 ◽  
Author(s):  
Diana Ainembabazi ◽  
Nan An ◽  
Jinesh Manayil ◽  
Kare Wilson ◽  
Adam Lee ◽  
...  
Keyword(s):  
Layered Double Hydroxides ◽  
Oxidation States ◽  
Secondary Amines ◽  
Primary Amines ◽  
Acid Dissolution ◽  
Oxidative Amination ◽  
Strong Function ◽  
Excellent Activity ◽  
High Yields ◽  
Double Hydroxides

<div> <p>The synthesis, characterization, and activity of Pd-doped layered double hydroxides (Pd-LDHs) for for acceptorless amine dehydrogenation is reported. These multifunctional catalysts comprise Brønsted basic and Lewis acidic surface sites that stabilize Pd species in 0, 2+, and 4+ oxidation states. Pd speciation and corresponding cataytic performance is a strong function of metal loading. Excellent activity is observed for the oxidative transamination of primary amines and acceptorless dehydrogenation of secondary amines to secondary imines using a low Pd loading (0.5 mol%), without the need for oxidants. N-heterocycles, such as indoline, 1,2,3,4-tetrahydroquinoline, and piperidine, are dehydrogenated to the corresponding aromatics with high yields. The relative yields of secondary imines are proportional to the calculated free energy of reaction, while yields for oxidative amination correlate with the electrophilicity of primary imine intermediates. Reversible amine dehydrogenation and imine hydrogenation determine the relative imine:amine selectivity. Poisoning tests evidence that Pd-LDHs operate heterogeneously, with negligible metal leaching; catalysts can be regenerated by acid dissolution and re-precipitation.</p> </div> <br>

ChemInform Abstract: Novel Silicon- and Tin-Containing Ferrocenophanes and Related Compounds as Lewis Acids.

ChemInform ◽  
2010 ◽  
Vol 31 (17) ◽  
pp. no-no
Author(s):  
Reiner Altmann ◽  
Olivier Gausset ◽  
Dagmar Horn ◽  
Klaus Jurkschat ◽  
Markus Schuermann ◽  
...  
Keyword(s):  
Lewis Acids ◽  
Related Compounds

Titration syntheses of polyaminosubstituted phthalocyanines via nucleophilic aromatic substitutions on zinc(II) 1,2,3,4,8,9,10,11,15,16,17,18,22,23,24,25-hexadecafluorophthalocyanine

2007 ◽  
Vol 11 (07) ◽  
pp. 537-546 ◽  
Author(s):  
Clifford C. Leznoff ◽  
Annette Hiebert ◽  
Sibel Ok
Keyword(s):  
Amino Acids ◽  
Chain Length ◽  
Secondary Amines ◽  
Primary Amines ◽  
Tertiary Butyl ◽  
Butyl Esters ◽  
Mild Conditions ◽  
Nucleophilic Aromatic Substitutions

Primary amines, secondary amines and tertiary butyl esters of amino acids are used as nucleophiles with zinc(II) hexadecafluorophthalocyanine to provide mixtures of mono and disubstituted fluorinated phthalocyanines under mild conditions, or polyaminosubstituted phthalocyanines when using the amines as solvents. Diamines give cyclic substituted phthalocyanines, binuclear or trinuclear phthalocyanines or mixtures of both types, depending on the chain length or structure of the diamine.

scholarly journals A Single-Step Synthesis of Azetidine-3-Amines

2020 ◽  
Author(s):  
Brian J Wang ◽  
Matthew Duncton
Keyword(s):  
Functional Groups ◽  
Late Stage ◽  
Single Step ◽  
Secondary Amines ◽  
High Yield ◽  
Primary Amines ◽  
Privileged Structure ◽  
One Step ◽  
Alternative Procedures ◽  
Approved Drugs

<div> <p>The azetidine group is frequently encountered within contemporary medicinal chemistry where it is viewed as a privileged structure. However, the introduction of an azetidine can be synthetically challenging. Herein, a straight-forward one step synthesis of azetidine-3-amines, starting from a bench stable, commercial material is presented. The reaction tolerates functional groups commonly encountered in biological-, medicinal- and agro-chemistry, and proceeds in moderate-to-high yield with secondary amines, and moderate-to-low yield with primary amines. The methodology compares favorably to recent alternative procedures and can be utilized in “any-stage” functionalization, including late-stage azetidinylation of approved drugs and other compounds with pharmacological activity.</p> </div>

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