A tandem oximation–cyclization route to Δ2-isoxazolines

Norman, Amber L.; Shurrush, Khriesto A.; Calleroz, Amanda T.; Mosher, Michael

doi:10.1016/j.tetlet.2007.07.146

Cited by 29 publications

(17 citation statements)

References 16 publications

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“…In this case clean reactions occurred, providing the expected products in high yields. Given the non-spontaneous cyclization of derivatives 5 into the corresponding isoxazolines 6, we successfully attempted to promote a closing to the heterocyclic ring by adding a base, since under basic catalysis b,g-unsaturated oximes 5 are able to isomerise 9 to the corresponding a,b-unsaturated oximes 5 0 with a high electrophilic activity so that an intramolecular Michael addition process can occur. Thus, compounds 5 in ethanol solution were treated with aqueous sodium hydroxide (ratio 1:1) for a few minutes.…”

Section: Resultsmentioning

confidence: 99%

“…Bond lengths ( A) Cl(1)eC (11) 1.7777 (18) O(2)eC(10) 1.451(2) Cl(2)eC (11) 1.7862(18) C(8)eC (9) 1.503(2) N(1)eC (8) 1.280(2) C(9)eC(10) 1.524(3) N(1)eO (2) 1.431(2) C(10)eC(11) 1.523 (3) Bond angles ( ) C(8)eN(1)eO (2) 108.86(15) O(2)eC(10)eC (11) 107.28(15) N(1)eO(2)eC (10) 108.87(13) O(2)eC(10)eC (9) 104.74(14) N(1)eC(8)eC (4) 121.86(17) C(11)eC(10)eC (9) 111.55(15) N(1)eC(8)eC (9)) 114.12(16) C(10)eC(11)eCl(1) 110.55(13) C(4)eC(8)eC (9) 124.00(16) C(10)eC(11)eCl (2) 108.90(13) C(8)eC(9)eC (10) 100.71 (15) Cl (1) …”

Section: Preparation Of 22-dichlorovinylacetophenone Oximesmentioning

confidence: 99%

“…2-Isoxazolines have been reported as biologically active compounds with antifungal, 6 antibacterial 7,8 and antidiabetic 9,10 properties. Certain drugs useful against cardiovascular 11 diseases and as anticoagulants 12,13 contain a 2-isoxazoline moiety.…”

Section: Introductionmentioning

confidence: 99%

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A new and efficient approach to isoxazolines. First synthesis of 3-aryl-5-dichloromethyl-2-isoxazolines

Guirado¹,

Martiz²,

Andreu³

et al. 2011

Tetrahedron

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a b s t r a c tAn efficient synthetic method for 3-aryl-5-dichloromethyl-2-isoxazolines has been established. Reactions between anhydrous chloral and acetophenones in hot acetic acid lead to 1-aryl-4,4,4-trichloro-3-hydroxybutan-1-ones (chloralacetophenones), which provided 1-aryl-4,4-dichlorobut-3-en-1-ones (2,2-dichlorovinylacetophenones) by dehydration and subsequent electrochemical reduction. These b,g-unsaturated enones reacted with hydroxylamine yielding oxime intermediates whose treatment with aqueous sodium hydroxide gave novel 3-aryl-5-dichloromethyl-2-isoxazolines in fair to high yields. The molecular structure of a member of this family of compounds, 5-dichoromethy1-3-(4-methoxyphenyl)-2-isoxazoline, was determined by X-ray crystallography.

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Section: Resultsmentioning

confidence: 99%

Section: Preparation Of 22-dichlorovinylacetophenone Oximesmentioning

confidence: 99%

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A new and efficient approach to isoxazolines. First synthesis of 3-aryl-5-dichloromethyl-2-isoxazolines

Guirado¹,

Martiz²,

Andreu³

et al. 2011

Tetrahedron

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“…Forschungsartikel parison, the use of (S,Rs)-X2 with an NH moiety only give trace amounts of 3 a (entry 11). Other palladium sources such as PdCl 2 , Pd(OAc) 2 , Pd(CH 3 CN) 2 Cl 2 , and allylpalladium(II) chloride gave 3 a in lower yield (entries [12][13][14][15]. Further base and solvent screening did not give better results (entries 16-21).…”

Section: Angewandte Chemiementioning

confidence: 99%

Enantioselective Synthesis of Isoxazolines Enabled by Palladium‐Catalyzed Carboetherification of Alkenyl Oximes

et al. 2020

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Reported here is a highly efficient Pd/Xiang‐Phos catalyzed enantioselective carboetherification of alkenyl oximes with either aryl or alkenyl halides, delivering various chiral 3,5‐disubstituted and 3,5,5‐trisubstituted isoxazolines in good yields with up to 97 % ee. The sterically bulky and electron‐rich (S,Rs)‐NMe‐X2 ligand is responsible for the excellent reactivities and enantioselectivities. The salient features of this transformation include mild reaction conditions, general substrate scope, good functional‐group tolerance, good yields, high enantioselectivities, easy scale‐up, and application in the late‐stage modification of bioactive compounds. The obtained products can be readily transformed into useful chiral 1,3‐aminoalcohols.

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“…They are versatile scaffolds for the synthesis of a wide variety of complex natural products and important pharmacophore in therapeutic chemistry . 2‐Isoxazolines are also known to exhibit interesting biological activities such as antifungal , antibacterial , anti‐convulsant , anti‐inflammatory , antiviral , analgesic , and anti‐HIV activities . One of the most general methods used to prepare 2‐isoxazolines involves 1,3‐dipolar cycloaddition between nitrile oxides and olefins .…”

Section: Introductionmentioning

confidence: 99%

A Simple, Efficient One‐Pot Synthesis of 2‐Isoxazoline Derivatives and their Antimicrobial Activity

Kumar

Sankar

Kim

2014

Journal of Heterocyclic Chem

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Synthesis of substituted 2‐isoxazolines derivatives with sulfone functional groups was accomplished by 1,3‐dipolar cycloaddition reaction. The 1,3‐dipolar nitrile oxides generated in situ by reacting α‐formaldoximes with N‐bromosuccinimide in the presence of triethylamine on reaction with activated alkenes in toluene at room temperature afford the corresponding 2‐isoxazolines in high yields. All the 2‐isoxazoline derivatives were assayed for their antibacterial activities against Staphylococcus aureus, Bacillus cereus, Escherichia coli, and Pseudomonas aeruginosa and antifungal activities against Aspergillus niger and Candida albicans. Most of the compounds showed good antibacterial and antifungal activities.

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A tandem oximation–cyclization route to Δ2-isoxazolines

Cited by 29 publications

References 16 publications

A new and efficient approach to isoxazolines. First synthesis of 3-aryl-5-dichloromethyl-2-isoxazolines

A new and efficient approach to isoxazolines. First synthesis of 3-aryl-5-dichloromethyl-2-isoxazolines

Enantioselective Synthesis of Isoxazolines Enabled by Palladium‐Catalyzed Carboetherification of Alkenyl Oximes

A Simple, Efficient One‐Pot Synthesis of 2‐Isoxazoline Derivatives and their Antimicrobial Activity

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