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1.
Acta Crystallogr E Crystallogr Commun ; 80(Pt 7): 789-794, 2024 Jun 01.
Article in English | MEDLINE | ID: mdl-38974149

ABSTRACT

A new mononuclear complex, penta-aqua-(cucurbit[6]uril-κ2 O,O')(nitrato-κ2 O,O')praseodymium(III) dinitrate 9.56-hydrate, [Pr(NO3)(CB6)(H2O)5](NO3)2·9.56H2O (1), was obtained as outcome of the hydro-thermal reaction between the macrocyclic ligand cucurbit[6]uril (CB6, C36H36N24O12) with a tenfold excess of Pr(NO3)3·6H2O. Complex 1 crystallizes in the P21/n space group with two crystallographically independent but chemically identical [Pr(CB6)(NO3)(H2O)5]2+ complex cations, four nitrate counter-anions and 19.12 inter-stitial water mol-ecules per asymmetric unit. The nona-coordinated PrIII in 1 are located in the PrO9 coordination environment formed by two carbonyl O atoms from bidentate cucurbit[6]uril units, two oxygen atoms from the bidentate nitrate anion and five water mol-ecules. Considering the differences in Pr-O bond distances and O-Pr-O angles in the coordination spheres, the coordination polyhedrons of the two PrIII atoms can be described as distorted spherical capped square anti-prismatic and muffin polyhedral.

2.
Beilstein J Org Chem ; 16: 281-289, 2020.
Article in English | MEDLINE | ID: mdl-32180844

ABSTRACT

Four-component reactions of 3-amino-1,2,4-triazole or 5-amino-1H-pyrazole-4-carbonitrile with aromatic aldehydes and pyruvic acid or its esters under ultrasonication were studied. Unusual for such a reaction type, a cascade of elementary stages led to the formation of 7-azolylaminotetrahydroazolo[1,5-a]pyrimidines.

3.
J Comb Chem ; 5(2): 145-8, 2003.
Article in English | MEDLINE | ID: mdl-12625704

ABSTRACT

A microwave-enhanced variation of the Kindler thioamide synthesis is introduced. Taking advantage of the sealed vessel capabilities of a dedicated single-mode microwave reacto,r a diverse selection of 13 aldehyde and 12 amine precursors was utilized in the construction of a representative 34-member library of substituted thioamides. The three-component condensations of aldehydes, amines, and elemental sulfur were carried out using 1-methyl-2-pyrrolidone (NMP) as solvent employing microwave flash heating at 110-180 degrees C for 2-20 min. A simple workup protocol allows the isolation of synthetically valuable primary, secondary, and tertiary thioamide building blocks in 83% average yield and >90% purity.


Subject(s)
Thioamides/chemical synthesis , Benzaldehydes , Combinatorial Chemistry Techniques/methods , Gas Chromatography-Mass Spectrometry , Indicators and Reagents , Magnetic Resonance Spectroscopy , Microwaves , Morpholines/chemical synthesis , Morpholines/chemistry , Piperazines/chemical synthesis , Piperazines/chemistry
4.
J Comb Chem ; 4(5): 501-10, 2002.
Article in English | MEDLINE | ID: mdl-12217023

ABSTRACT

Solid-phase and solution-phase protocols for the synthesis of furo[3,4-d]pyrimidines, pyrrolo[3,4-d]pyrimidines, and pyrimido[4,5-d]pyridazines are reported. The multistep solid-phase sequence involves the initial high-speed, microwave-promoted acetoacetylation of hydroxymethylpolystyrene resin with methyl 4-chloroacetoacetate. The immobilized 4-chloroacetoacetate precursor was subsequently subjected to three-component Biginelli-type condensations employing urea and a variety of aromatic aldehydes. The resulting 6-chloromethyl-functionalized resin-bound dihydropyrimidones served as common chemical platforms for the generation of the desired heterobicyclic scaffolds using three different traceless cyclative cleavage strategies. The corresponding furo[3,4-d]pyrimidines were obtained by microwave flash heating in a rapid, thermally triggered, cyclative release. Treatment of the chloromethyl dihydropyrimidone intermediates with a variety of primary amines followed by high-temperature microwave heating furnished the anticipated pyrrolo[3,4-d]pyrimidine scaffolds via nucleophilic cyclative cleavage. In a similar way, reaction with monosubstituted hydrazines resulted in the formation of pyrimido[4,5-d]pyridazines. All compounds were obtained in moderate to good overall yields and purities.

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