Two methods for conversion of an aromatic aldehyde to a 4‐arylpyridine. A method for preparation of 3‐alkyl‐4‐arylpyridines

Carbateas, P. M.; Williams, Gordon L.

doi:10.1002/jhet.5570110531

Cited by 16 publications

(2 citation statements)

References 4 publications

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“…Initial efforts were focused on ozonolysis, which was performed successfully, but proved unfeasible for larger scale reactions. However, oxidation of the furan moiety using nitric acid and ammonium metavanadate 24 led to the desired pinenesubstituted 2-pyridinecarboxylic acid. Isolation of this amphoteric and amphiphilic compound proved to be difficult, and the subsequent esterification 25 was performed without prior purification of the acid.…”

Section: Resultsmentioning

confidence: 99%

“…The reaction mixture was then poured into hexanes (150 mL) and neutralized with an aqueous solution of saturated sodium bicarbonate. The water layer was extracted with hexanes (3 × 100 mL), and the combined organic layers were then washed with water (3 × 100 mL), dried over sodium sulfate and concentrated on a rotary evaporator: yield 5.7 g (56%); brown oil; 1 H NMR (400 MHz, CDCl3) δ 0.60 (s, 3H), 1.19 (d, J ) 9.7 Hz, 1H), 1.40-1.45 (m, 6H), 2.32 (quint, J1 ) 2.9 Hz, J2 ) 5.6 Hz, J3 ) 8.6 Hz, J4 ) 11.5 Hz, 1H), 2.66-2.74 (m, 1H), 2.88 (t, J ) 5.4 Hz, 1H), 3.01 (d, J ) 2.8 Hz, 2H), 4.45 (q, J1 ) 6.5 Hz, J2 ) 7.1 Hz, J3 ) 7.7 Hz, 2H), 7.91 (s, 1H), 8.26 (s, 1H); 13 (7), 200 (30), 186 (37), 170 (39), 158 (100), 141 (27), 128 (79), 117 (23), 103 (24), 84 (22), 77 (68), 69 (40).…”

Section: Methodsmentioning

confidence: 99%

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Synthesis and Characterization of Highly Conjugated, Chiral Bridging Ligands

Sauers

Bernhard

2004

J. Org. Chem.

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This paper describes the synthesis of four chiral derivatives of the electronically highly conjugated tetra-2-pyridylpyrazine (TPPZ) bridging ligand, which are denoted (R)- and (S)-4,5- and 5,6-pineno-tetra-2-pyridylpyrazine (PTPPZ). Preparation of these ligands was undertaken through the use of commercially available, enantiomerically pure (1R)- and (1S)-alpha-pinene, which was functionalized and subsequently employed in a Krohnke pyridine synthesis involving a furan-substituted pyridinium salt to yield a chiral, furan-substituted pyridyl intermediate. Oxidative degradation and subsequent reduction of this furan led to a chiral, substituted 2-pyridylaldehyde, which underwent a pyridoin condensation followed by cyclization to produce the final PTPPZ ligands.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Synthesis and Characterization of Highly Conjugated, Chiral Bridging Ligands

Sauers

Bernhard

2004

J. Org. Chem.

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Oxidative Cleavage of Furans

Merino

2015

Organic Reactions

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Oxidative ring cleavage reactions of furans constitute a group of important transformations that have found wide utility in synthetic organic chemistry. These processes have been used to prepare a variety of 1,4‐dicarbonyl compounds including 1,4‐dioxoalkenes, 4‐oxoalkenals, 4‐oxoalkenoic acids, and their derivatives such as 4‐hydroxybutenolides and 2,5‐dialkoxydihydrofurans. Oxidations of furfuryl alcohols (Achmatowicz reaction) and furfuryl amines (aza‐Achmatowicz reaction) provide access to highly functionalized heterocyclic structures that have been employed as intermediates in synthetic routes for the preparation of complex molecules including carbohydrates and alkaloids. Complete oxidative degradation of the furan ring affords carboxylic acids; thus the oxygen heterocycle has served as a masked carboxyl group in many synthetic studies. These transformations and their applications in total syntheses are covered in this chapter.

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Aryl Rings Are Part of the Darpone Pharmacophore

Schultz

Link

Kunick

2001

Arch. Pharm. Pharm. Med. Chem.

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In order to investigate structure‐activity relationships in the antiproliferative darpone series, the derivatives 8a and 8b lacking the aryl substituents in either 2‐ or 4‐position were synthesized and evaluated for cancer cell growth inhibition. Since both 8a and 8b were devoid of noteworthy antiproliferative activity, both aryl substituents can be considered as part of the darpone pharmacophore.

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Two methods for conversion of an aromatic aldehyde to a 4‐arylpyridine. A method for preparation of 3‐alkyl‐4‐arylpyridines

Cited by 16 publications

References 4 publications

Synthesis and Characterization of Highly Conjugated, Chiral Bridging Ligands

Synthesis and Characterization of Highly Conjugated, Chiral Bridging Ligands

Oxidative Cleavage of Furans

Aryl Rings Are Part of the Darpone Pharmacophore

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