On the oximation of diaryl‐β‐diketones

Bandiera, Tiziano; Grünanger, Paolo; Albini, Franca Marinone

doi:10.1002/jhet.5570290609

Cited by 43 publications

(20 citation statements)

References 28 publications

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“…Isoxazoles are heteroaromatic compounds that are commonly used as synthetic building blocks and can be found in natural products and pharmaceuticals 31. However, their syntheses via [3+2] cycloaddition reactions of alkenes/alkynes with nitrile oxides,32 and the reactions of hydroxylamine with 1,3‐dicarbonyl compounds,33 α,β‐unsaturated carbonyl compounds34 and α,β‐unsaturated nitriles35 are hampered by the use of stoichiometric amounts of reagents, strong acids/bases, high reaction temperatures, prolonged reaction times and poor regioselectivity. Thus, the development of new methods for isoxazole synthesis is of importance in organic chemistry 36.…”

Section: Resultsmentioning

confidence: 99%

Cyclometallated Gold(III) Complexes as Effective Catalysts for Synthesis of Propargylic Amines, Chiral Allenes and Isoxazoles

Kung

et al. 2013

Adv Synth Catal

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Cl 2 ] 1a-l (HC _ N = arylpyridines) and a PEG-linked complex 1m were synthesized. Complexes 1a-m are effective in catalyzing the synthesis of propargylic amines, chiral allenes and isoxazoles. Six-membered ring cyclometallated goldA C H T U N G T R E N N U N G (III) complexes 1f-l exhibited higher catalytic activity than five-membered ring cyclometallated goldA C H T U N G T R E N N U N G (III) complexes 1a-e. The diastereoselectivity of propargylic amines could be tuned by using chiral aldehyde and/ or amine substrates. Excellent enantioselectivities (90-98% ee) were achieved in chiral allene synthesis. Chiral allene racemization could be minimized by using 1f as catalyst. The PEG-linked catalyst 1m is the most catalytically active towards synthesis of propargylic amines, in which case a product turnover of 900 was achieved. Moreover, 1m could be repeatedly used for 12 reaction cycles, leading to an overall turnover number of 872.

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Section: Resultsmentioning

confidence: 99%

Cyclometallated Gold(III) Complexes as Effective Catalysts for Synthesis of Propargylic Amines, Chiral Allenes and Isoxazoles

Kung

et al. 2013

Adv Synth Catal

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“…A review of the literature on the structural assignments reveals that data are scanty and controversial [15,[18][19][20][21]. For example, the oximes originated from 1-aryl-3-phenylpropane-1,3-diones have subsequently been demonstrated to give rise either to one of the two possible isoxazoles or to a mixture of both isomers [22]. From a survey of the cases reported in the literature, it became obvious that many factors can influence the yield and regioselectivity of the isomers.…”

Section: Introductionmentioning

confidence: 99%

Structural investigation of 3,5‐disubstituted isoxazoles by ¹H‐nuclear magnetic resonance

Sechi¹,

Sannia²,

Orecchioni³

et al. 2003

Journal of Heterocyclic Chem

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This work is dedicated to the memory of Prof. Paolo Sanna HIV-1 integrase (IN) is a very promising and validated target for the development of therapeutic agents against AIDS. In an effort to design and synthesize biological isosteric analogs of β-diketoacid-containing inhibitors of IN, we prepared a series of substituted isoxazole carboxylic acids. Several of these compounds inhibited catalytic activities of purified IN at micromolar concentration range. With an aim to prepare a large number of analogues based on the isoxazole pharmacophore we focused our study on a series of 3,5-disubstituted isoxazole isomers. For a rapid structural analysis we discovered a convenient 1 H-nmr method for distinguishing between isomeric structures based on their H-4 assignments. This "finger print" approach to isomer identification will be useful in combinatorial chemistry settings where a mixture can be further derivatized.

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“…120-121°C (lit. [26] mp: 119-120°C). IR nujol ν (cm -1 ) = 1611, 1582, 1528, 1450, 1296, 1251, 1177.…”

Section: -(4-methoxyphenyl)-5-phenylisoxazole (2b) General Methods Fomentioning

confidence: 99%

K2CO3-Mediated Regioselective Synthesis of Isoxazoles and Pyrazolines

Kidwai¹,

Kukreja²,

Thakur

2006

LOC

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3,5-Diarylisoxazoles and 1,3,5-triarylpyrazolines are synthesized via Michael addition of "hydroxylamine hydrochloride, phenylhydrazine" respectively over chalcones followed by cyclization using K 2 CO 3 as solid support. Reactions are shown to be highly regioselective regardless of the nature of the substituent in the substrates and afforded single isoxazole and pyrazoline isomer in excellent yields.

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On the oximation of diaryl‐β‐diketones

Cited by 43 publications

References 28 publications

Cyclometallated Gold(III) Complexes as Effective Catalysts for Synthesis of Propargylic Amines, Chiral Allenes and Isoxazoles

Cyclometallated Gold(III) Complexes as Effective Catalysts for Synthesis of Propargylic Amines, Chiral Allenes and Isoxazoles

Structural investigation of 3,5‐disubstituted isoxazoles by ¹H‐nuclear magnetic resonance

K2CO3-Mediated Regioselective Synthesis of Isoxazoles and Pyrazolines

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On the oximation of diaryl‐β‐diketones

Cited by 43 publications

References 28 publications

Cyclometallated Gold(III) Complexes as Effective Catalysts for Synthesis of Propargylic Amines, Chiral Allenes and Isoxazoles

Cyclometallated Gold(III) Complexes as Effective Catalysts for Synthesis of Propargylic Amines, Chiral Allenes and Isoxazoles

Structural investigation of 3,5‐disubstituted isoxazoles by 1H‐nuclear magnetic resonance

K2CO3-Mediated Regioselective Synthesis of Isoxazoles and Pyrazolines

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Structural investigation of 3,5‐disubstituted isoxazoles by ¹H‐nuclear magnetic resonance