ChemInform Abstract: The Synthesis of Dipeptides of Aminoalkylphosphonic Acid and Their Cyclic Compounds

ChemInform ◽  
1990 ◽  
Vol 21 (49) ◽  
Author(s):  
R.-Y. CHEN ◽  
S.-C. DAN
Keyword(s):  
Cyclic Compounds ◽  
Aminoalkylphosphonic Acid

SOME DIRECTIONS IN THE MODIFICATION OF AZOLES

2020 ◽  
Vol 5 (443) ◽  
pp. 85-91
Author(s):  
Ibrayev M.K., ◽  
◽  
Takibayeva A.T., ◽  
Fazylov S.D., ◽  
Rakhimberlinova Zh.B., ◽  
...  
Keyword(s):  
13C Nmr Spectroscopy ◽  
Biologically Active Compounds ◽  
Biologically Active ◽  
Active Compounds ◽  
Synthesis Conditions ◽  
Alkaloid Cytisine ◽  
Azole Ring ◽  
Cyclic Compounds ◽  
New Compounds ◽  
Derivatives Of

This article presents studies on the targeted search for new derivatives of azoles, such as benzthiazole, 3,5-dimethylpyrazole, 1,3,4-oxadiazole-2-thione, 1,3,4-thiadiazole. The possibility of combining in one molecule of the azole ring with other cyclic compounds: the alkaloid cytisine, morpholine, furan and some arenes has been studied. To obtain new compounds, the reactions of bromination, acylation, and interaction with isothiocyanates were studied. Optimal synthesis conditions were studied for all reactions. It was found that the reaction of 4-bromo-3,5-dimethylpyrazole with isothiocyanates, in contrast to the previously written derivatives of anilines, takes a longer time and requires heating the reaction mixture. The combination of a pirasol fragment with halide substituents often results in an enhanced therapeutic effect. The synthesized 2-bromine-N-(6-rodanbenzo[d]thiazole-2-yl)acetamide, due to the alkylbromide group, is an important synth in the synthesis of new benzthiazole derivatives. Its derivatives combine in one molecule the rest of rhodanbenzthiazole with alkaloid cytisine and biogenic amine morpholine and are potentially biologically active compounds, since the molecule structure contains several pharmacophoric fragments: benzthiazole and alkaloid (amine) heterocycles, rhodane and urea groups. The mechanism of formation of 1,3,4-oxadiazole-2-tyons from hydrazides under action on them by carbon disulfide was studied and assumed. It was shown that dithiocarbamates in acidic medium decompose with the release of hydrogen sulfide and the formation of highly reactive isothiocyanate group. Then, intra-molecular cyclization occurs, with the formation of end products - 1,3,4-oxadiazole-2-thions. The structures of the synthesized compounds were studied by 1H and 13C NMR spectroscopy. All synthesized substances are potentially biologically active compounds, since they contain several pharmacophore fragments in their structure.

Synthesis and stability of 1-aminoalkylphosphonic acid quaternary ammonium salts

2021 ◽  
Author(s):  
Tomasz K. Olszewski ◽  
Anna Brol
Keyword(s):  
Phosphonic Acid ◽  
Quaternary Ammonium ◽  
Alkylating Agent ◽  
Quaternary Ammonium Salts ◽  
Ammonium Salts ◽  
Aminoalkylphosphonic Acid

An effective protocol for quaternization of simple 1-aminoalkylphosphonic acids under basic conditions and using Me2SO4 as convenient alkylating agent is reported. In the course of reaction phosphonic acid quaternary ammonium...

Synthesis of sp3-Enriched β-Fluoro Sulfonyl Chlorides

Synthesis ◽  
2020 ◽  
Author(s):  
Oleksandr O. Grygorenko ◽  
Rustam Gurbanov ◽  
Andriy Sokolov ◽  
Sergey Golovach ◽  
Kostiantyn Melnykov ◽  
...  
Keyword(s):  
Drug Discovery ◽  
Double Bond ◽  
Building Blocks ◽  
Protecting Groups ◽  
Sulfonyl Chlorides ◽  
Wide Range ◽  
Cyclic Compounds

AbstractA three-step approach to the synthesis of sp3-enriched β-fluoro sulfonyl chlorides starting from alkenes is reported. The method was successfully applied to a wide range of acyclic and cyclic substrates, bearing either an exocyclic or an endocyclic double bond. The procedure worked with a wide range of substrates and tolerated a number of functional and protecting groups. Moreover, the target cyclic compounds were obtained as single cis diastereomers on a multigram scale. The title compounds are promising building blocks for drug discovery that can be used to obtain sp3-enriched β-fluoro and α,β-unsaturated sulfonamides.

scholarly journals Structure-Acid Lability Relationship of N-alkylated α,α-dialkylglycine Obtained via a Ugi Multicomponent Reaction

Molecules ◽  
2021 ◽  
Vol 26 (1) ◽  
pp. 197
Author(s):  
Iván Ramos-Tomillero ◽  
Marisa K. Sánchez ◽  
Hortensia Rodríguez ◽  
Fernando Albericio
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Structural Features ◽  
Amide Bond ◽  
Acidic Media ◽  
Phase Synthesis ◽  
Acyl Chains ◽  
Cyclic Compounds ◽  
Relationship Of ◽  
Fine Tune

Using the classical Ugi four-component reaction to fuse an amine, ketone, carboxylic acid, and isocyanide, here we prepared a short library of N-alkylated α,α-dialkylglycine derivatives. Due to the polyfunctionality of the dipeptidic scaffold, this highly steric hindered system shows an interesting acidolytic cleavage of the C-terminal amide. In this regard, we studied the structure-acid lability relationship of the C-terminal amide bond (cyclohexylamide) of N-alkylated α,α-dialkylglycine amides 1a–n in acidic media and, afterward, it was established that the most important structural features related to its cleavage. Then, it was demonstrated that electron-donating effects in the aromatic amines, flexible acyl chains (Gly) at the N-terminal and the introduction of cyclic compounds into dipeptide scaffolds, increased the rate of acidolysis. All these effects are related to the ease with which the oxazolonium ion intermediate forms and they promote the proximity of the central carbonyl group to the C-terminal amide, resulting in C-terminal amide cleavage. Consequently, these findings could be applied for the design of new protecting groups, handles for solid-phase synthesis, and linkers for conjugation, due to its easily modulable and the fact that it allows to fine tune its acid-lability.

ChemInform Abstract: 2-Alkynylbenzaldehyde: A Versatile Building Block for the Generation of Cyclic Compounds

ChemInform ◽  
2013 ◽  
Vol 44 (18) ◽  
pp. no-no
Author(s):  
Huanhuan Wang ◽  
Yunyan Kuang ◽  
Jie Wu
Keyword(s):  
Building Block ◽  
Cyclic Compounds

ortho-Diquaternary aromatic compounds. II. Synthesis and spectral properties of β,β′-dihydroxy-2,3-di-t-butylnaphthalene and related crowded aromatics

1969 ◽  
Vol 47 (23) ◽  
pp. 4313-4318 ◽  
Author(s):  
L. R. C. Barclay ◽  
G. R. Nixon ◽  
H. M. Foote ◽  
S. L. Barclay
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Aromatic Compounds ◽  
Spectral Properties ◽  
Bond Angle ◽  
Chemical Shifts ◽  
Dimethyl Ester ◽  
Selenium Dioxide ◽  
Hydride Reduction ◽  
Cyclic Compounds ◽  
Compression Effects

Cyclialkylation of naphthalene with 2,2,5,5-tetramethyltetrahydrofuranone yielded 2-keto-1,1,4,4-tetramethyl-1,2,3,4-tetrahydroanthracene (1). Selenium dioxide oxidation of 1 yielded the corresponding diketone (3) and periodate cleavage of 3 yielded 2,3-naphthalene-diisobutyric acid (4). Hydride reduction of the dimethyl ester (6) of 4 yielded the diol, β,β′-dihydroxy-2,3-di-t-butylnaphthalene (7). The relative chemical shifts of aromatic protons of 1,2,4,5-tetraalkylbenzenes containing gem dimethyls are rationalized in terms of compression effects exerted by the bulky ortho groups. Nuclear magnetic resonance and ultraviolet spectral results for the ortho di-t-butyl aromatic derivatives 4, 6, and 7 are compared to the model cyclic compounds 1 and anhydride (5) of 4 in terms of the strain caused by bond angle deformations in the side chains.

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