New heterocycles from 8‐hydroxyquinoline via dipolar 1,3‐cycloadditions: Synthesis &amp; biological evaluation

Bahloul, Abdelmejid; Sebban, Abdelfatah; Dardari, Zainaba; Boudouma, Mohammed; Kitane, S.; Belghiti, Touria; Joly, Jean‐Pierre

doi:10.1002/jhet.5570400207

Cited by 10 publications

(2 citation statements)

References 30 publications

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“…(E)-7-(1-Propenyl)-8-quinolinol (13) (Scheme 1). 43 General Procedure for the Conjugative Migration. 7-Allyl-8-quinolinol (185.2 mg, 1.0 mmol) dissolved in toluene (2.5 mL), Pd(dba) 2 from a 0.01 mg µL -1 stock solution in toluene (288.0 µL, 5.0 µmol), P(tBu) 3 from a 0.02 mg µL -1 stock solution in toluene (50.6 µL, 5.0 µmol), and isobutyryl chloride from a 0.01 mg µL -1 stock solution in toluene (53.3 µL, 5.0 µmol) were reacted for 21 h at 80 °C.…”

Section: Methodsmentioning

confidence: 99%

In Situ Generated Bulky Palladium Hydride Complexes as Catalysts for the Efficient Isomerization of Olefins. Selective Transformation of Terminal Alkenes to 2-Alkenes

et al. 2010

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Application of an in situ generated bulky palladium(II) hydride catalyst obtained from a 1:1:1 mixture of Pd(dba)(2), P(tBu)(3), and isobutyryl chloride provides an efficient protocol for the isomerization and migration of a variety of olefins. In addition to the isomerization of (Z)- to (E)-olefins, the conjugative migration of allylbenzenes, allyl ethers, and amines was effectively achieved in near-quantitative yields and with excellent functional group tolerance. Catalyst loadings in the range of 0.5-1.0 mol % were typically applied, but even loadings as low as 0.25 mol % could be achieved when the reactions were performed under neat conditions. More interestingly, the investigated catalyst proved to be selective for converting terminal alkenes to 2-alkenes. This one-carbon migration process for monosubstituted olefins provides an alternative catalyst, which bridges the gap between the allylation and propenylation/vinylation protocols. Several substrates, including homoallylic alcohols and amines, were selectively transformed into their corresponding 2-alkenes, and examples using enantiomerically enriched substrates provided products without epimerization at the allylic stereogenic carbon centers. Finally, some mechanistic investigations were undertaken to understand the nature of the active in situ generated Pd-H catalyst. These studies revealed that the catalytic system is highly dependent on the large steric demand of the P(tBu)(3) ligand. The use of an alternative ligand, cataCXium PinCy, also proved effective for generating an active catalyst, and it was demonstrated in some cases to display better selectivity for the one-carbon shifts of terminal olefins. A possible intermediate involved in the preparation of the active catalyst was characterized by its single-crystal X-ray structure, which revealed a monomeric tricoordinated palladium(II) acyl complex, bearing a chloride ligand.

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Section: Methodsmentioning

confidence: 99%

In Situ Generated Bulky Palladium Hydride Complexes as Catalysts for the Efficient Isomerization of Olefins. Selective Transformation of Terminal Alkenes to 2-Alkenes

et al. 2010

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“…The analysis of publications [9][10][11] reveals a limited number of isoxazoline derivatives linked to the other heterocycles by a methylene bridge. It was therefore feasible to extend our method [12] of 3-arylpyrimidinedicarboxylates synthesis on their 3-allyl analogs and to use the latter for building up an isoxazoline ring.…”

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confidence: 99%

Heterocyclizations of functionalized heterocumulenes with C,N-, C,O-, and C,S-binucleophiles: XIII. Synthesis of dialkyl 2-oxo-3-allyl-1,2,3,6-tetrahydropyrimidine-4,5-dicarboxylates and their reaction with arylhydroxymoyl chlorides

2011

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Dialkyl 2-oxo-3-allyl-1,2,3,6-tetrahydropyrimidine-4,5-dicarboxylates obtained by condensation of 1-chlorobenzyl isocyanates with N-allylfumarates reacted regioselectively with arylhydroxymoyl chlorides with the formation of dialkyl 6-aryl-3-[(3-aryl-4,5-dihydro-5-isoxazolyl)methyl]-2-oxo-1,2,3,6-tetrahydropyrimidine-4,5-dicarboxylates.3,4-Dihydropyrimidine ring is the structural fragment governing the biological activity of many organic compounds [2][3][4]. Therewith the useful properties of 3,4-dihydropyrimidine derivatives are essentially affected by the character of substituents at the carbon atoms of the ring. Yet the effect of the substituents at nitrogen atoms remains practically nonstudied to a certain extent because of the lack of methods of the selective functionalization of the nitrogen atoms with biophore moieties. To the latter the isoxazoline heterocycle certainly belongs for among its derivatives substances are found with a wide range of the biologic action [5][6][7][8].The analysis of publications [9-11] reveals a limited number of isoxazoline derivatives linked to the other heterocycles by a methylene bridge. It was therefore feasible to extend our method [12] of 3-arylpyrimidinedicarboxylates synthesis on their 3-allyl analogs and to use the latter for building up an isoxazoline ring. ___________________ * For Communication XII, see [1].It was established that 1-chlorobenzyl isocyanates Іа-Ie reacted with previously unknown dialkyl N-allylaminofumarates ІІа, IIb in toluene solution at room temperature giving dialkyl 2-oxo-3-allyl-6-aryl-1,2,3,6-tetrahydropyrimidine-4,5-dicarboxylates ІІІа-IIIh in 45-83% yields. The structure of the latter is confi rmed by 1 Н and 13 С NMR spectra containing typical doublets of protons Н 6 in the range 5.23-5.42 ppm and signals of atoms С 6 in the range 51.86-53.02 ppm. The presence of the asymmetric carbon center in the position 6 of the heterocycle results in the diastereotopic character of the methylene group of the allyl substituent leading to the complex multiplicity of the signal of allyl protons in the 1 Н NMR spectrum.Among the versatile procedures for the preparation of isoxazoline derivatives the version should be specially indicated of 1,3-dipolar addition of nitrile oxides to alkenes, in particular, to functionalized ones, which is characterized by high regioselectivity [13,14]. We demonstrated that 3-allylpyrimidin-2-ones ІІІb, IIId, IIIe-IIIh also reacted regioselectively with hydroxymoyl chlorides IVа-IVb in the presence of triethylamine, i.e.,

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New Heterocycles from 8‐Hydroxyquinoline via Dipolar 1,3‐Cycloadditions: Synthesis and Biological Evaluation.

et al. 2003

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New heterocycles from 8‐hydroxyquinoline via dipolar 1,3‐cycloadditions: Synthesis & biological evaluation

Cited by 10 publications

References 30 publications

In Situ Generated Bulky Palladium Hydride Complexes as Catalysts for the Efficient Isomerization of Olefins. Selective Transformation of Terminal Alkenes to 2-Alkenes

In Situ Generated Bulky Palladium Hydride Complexes as Catalysts for the Efficient Isomerization of Olefins. Selective Transformation of Terminal Alkenes to 2-Alkenes

Heterocyclizations of functionalized heterocumulenes with C,N-, C,O-, and C,S-binucleophiles: XIII. Synthesis of dialkyl 2-oxo-3-allyl-1,2,3,6-tetrahydropyrimidine-4,5-dicarboxylates and their reaction with arylhydroxymoyl chlorides

New Heterocycles from 8‐Hydroxyquinoline via Dipolar 1,3‐Cycloadditions: Synthesis and Biological Evaluation.

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