Heterocycles derived from the condensation of 1,3‐propanediamine with phthalic acid derivatives

Gaozza, Carlos H.; Grinberg, Horacio; Lamdan, Sámuel

doi:10.1002/jhet.5570090422

Cited by 12 publications

(3 citation statements)

References 6 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…That indicated a reverse hydrolysis resulted in a pyrrolidine cycle opening of 8a-c because of the contact with atmospheric moisture, similar to that occurred with 2,3,4,6-tetrahydropyrimido[2,1-a]isoindol-6-one under the action of different nucleophiles. 37 A similar effect was also observed when dissolving compounds 8a-c in non-dried solvents such as acetone and DCM. In contrast, the hydrolysis of 2-aminopyrimidoisoindole-dione 8e did not occur under working conditions, neither on contact with atmospheric moisture nor when suspended in water.…”

Section: Paper Synthesismentioning

confidence: 53%

2-Carbamimidoylbenzoic Acid as a New Effective and Available Precursor for the Synthesis of Substituted 2-(Pyrimidin-2-yl)benzoic Acids

Tkachuk

Shishkanu

Tkachuk³

et al. 2020

Synthesis

View full text Add to dashboard Cite

A new approach to the synthesis of 2-(pyrimidin-2-yl)benzoic acids based on the ring contraction of the 2-carbamimidoylbenzoic acid [(2-amidinobenzoic) acid] with 1,3-dicarbonyl compounds and their synthetic equivalents has been developed. The intramolecular condensation of the obtained acids with 1,3-dielectrophiles proceeds with the formation of the 4,6-dihydropyrimido[2,1-a]isoindole-4,6-dione system, the pyrrolidone ring of which is easily opened under the action of weak nucleophiles. The reaction of 2-amidinobenzoic acid with chromones, which have an aryloxy group at 3-position does not stop at the step of pyrimidine ring formation and undergoes further spontaneous cyclization into 2-(benzo[4,5]furo[3,2-d]pyrimidin-2-yl)benzoic acids.

show abstract

Section: Paper Synthesismentioning

confidence: 53%

2-Carbamimidoylbenzoic Acid as a New Effective and Available Precursor for the Synthesis of Substituted 2-(Pyrimidin-2-yl)benzoic Acids

Tkachuk

Shishkanu

Tkachuk³

et al. 2020

Synthesis

View full text Add to dashboard Cite

show abstract

“…34a,b a n = 2, b n = 3 NH 2 (CH 2 ) 2 NH 2 NH 2 (CH 2 ) 3 NH 2 or n n Earlier [51] the synthesis of compound 34b from dimethyl phthalate and 1,3-diaminopropane was described.…”

Section: Dibenzotetraazamacroheterocycles Containing Amide Fragmentsmentioning

confidence: 99%

Dibenzotetraazamacroheterocycles: Synthesis and properties. (Review)

Kulikov

Pavlovsky

Андронати

2005

Chem Heterocycl Compd

View full text Add to dashboard Cite

Data on the synthesis, complexing ability, practical applications, and biological activity of dibenzotetraazamacroheterocycles of the azacrown ether, amide, and azomethinedibenzotetraazacycloalkane types and also dibenzotetraazamacroheterocycles containing amide and azomethine fragments are classified and analyzed.At present the chemistry of nitrogen macrocycles is developing at a very high rate. Many of the compounds are highly effective extractants for metal ions [1-3], find widespread use as contrast agents for magnetic resonance imaging [4][5][6][7][8], and can also be used as precursors in the biosynthesis of certain types of alkaloids [9] and also as ion-selective [10] and fluorescent [11] receptors and as agents for the transport of ions through a liquid membrane in dialysis and electrodialysis [12,13]. Chiral macrocyclic tetraamides are used as stationary phase in liquid chromatography [14]. The potentialities of nitrogen macrocycles in theoretical and practical respects have not been exhausted, and further research in the field is promising.In the last 15 years there have been a fairly large number of monographs and reviews in which aspects of the synthesis, properties, and applications of azamacroheterocycles and their metal complexes have been touched upon [15][16][17][18][19][20][21][22][23][24][25][26]. However, there have been significantly fewer publications devoted to the various classes of dibenzotetraazamacroheterocycles (e.g., dibenzotetraaza [14]annulenes [27][28][29], macrocyclic Schiff bases based on 2,6-diformylphenols [30]). Dibenzotetraazamacroheterocycles have found use as effective extractants for metal ions and as spectrophotometric agents [31][32][33], are used in the design of new magnetic materials [34], etc. To fill the gap we considered it desirable to analyze existing published material on the synthesis, complexation, and practical applications of dibenzotetraazamacrocycles of the azacrown ether, amide, azomethine, and dibenzotetraazacycloalkane types and also dibenzotetraazamacrocycles containing amide and azomethine fragments.

show abstract

“…1 Here, the most typical examples of synthesis based on this approach are mentioned. 1,3-Diaminopropane 92 reacts with o-acylbenzoic acids 93, o-acylbenzaldehydes 94 and phthalic anhydride 95 (but not with phthaloyl dichloride or phthalates 57 ) to give hexahydropyrimido[2,1-a]isoindol-6-ones 96 or the tetrahydro derivatives 97 and 98, respectively. This reaction usually occurs upon boiling of the reaction mixture in toluene or xylene with azeotropic distillation of water in the presence of catalytic amounts of toluene-p-sulfonic acid (for 93, the yields exceed 60%).…”

Section: Synthesis Of Pyrimido[21-a]isoindole Derivativesmentioning

confidence: 99%