A facile one-pot synthesis of 2-fluoroalkyl 1,3-imidazolines and 1,3-oxazolines through imidoyl halide intermediates

Jiang, Haizhen; Sun, Lixin; Yuan, Shijie; Lü, Wenjun; Wan, Wen; Zhu, Shizheng; Hao, Jian

doi:10.1016/j.tet.2012.01.086

Cited by 15 publications

(5 citation statements)

References 31 publications

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“…Our initial experiments on the reaction of 2-bromodifluoromethyl-1,3-oxazoline ( 1a ) with phenolate disclosed that a gem -difluoromethylene-linked 1,3-oxazoline-contaning phenyl ether ( 2aa ) could be obtained exclusively. The reaction was carried out in a 1:1.1:2 1a :PhOH:NaH molar ratio in DMF at 80 °C.…”

Section: Resultsmentioning

confidence: 99%

Nucleophile-Dependent Regioselective Reaction of (S)-4-Benzyl-2-Fluoroalkyl-1,3-Oxazolines

Jiang

Yan

et al. 2013

J. Org. Chem.

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Nucleophile-dependent regioselectivities in the nucleophilic reaction of (S)-4-benzyl-2-fluoroalkyl-1,3-oxazoline to different types of fluorinated compounds were investigated experimentally and theoretically. The ring opening of (S)-4-benzyl-2-bromodifluoromethyl-1,3-oxazoline by arenethiolates exclusively occurred at the C5 position of the 1,3-oxazoline ring, whereas completely different regioselectivity was observed for a unimolecular radical nucleophilic substitution (S(RN)1) at the terminal bromine atom of the CF2Br group when arenolates were employed as the nucleophiles. The reaction of (S)-4-benzyl-2-trifluoromethyl-1,3-oxazoline with nucleophiles such as arenethiols, arenols, and TMSCl underwent nucleophilic ring opening in a regiospecific way, while the use of TMSCF3 was determined to proceed through nucleophilic addition to the C═N bond.

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Section: Resultsmentioning

confidence: 99%

Nucleophile-Dependent Regioselective Reaction of (S)-4-Benzyl-2-Fluoroalkyl-1,3-Oxazolines

Jiang

Yan

et al. 2013

J. Org. Chem.

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“…The proposed mechanism for this cyclization is illustrated in Scheme 9. First, the Cu(II)-(IAA) 2 activates the nitrile group of 33 and forms nitrogen cation (36). After that, the nucleophilic attack of 34 affords intermediate amidine (37), followed by the formation of imidazolidine (38).…”

Section: Methods A: Synthesis Of Imidazolines From 12-diaminesmentioning

confidence: 99%

“…In 2012, a facile one-pot synthesis of 2-imidazolines (57) was reported by Hao and co-workers from the condensation of N-substituted ethylenediamines (54) with a fluorinated carboxylic acid in the presence of triphenylphosphine (PPh 3 ) and carbon tetrachloride (CCl 4 ) (Scheme 15). [36] The fluorinated amide (55) generated in the first step, converted to the intermediate imidoyl chloride (56) in the presence of triethylamine (TEA) and PPh 3 /CCl 4 . In the final stage, 2imidazoline is formed by the intramolecular cyclization of imidoyl chloride 56.…”

Section: Methods A: Synthesis Of Imidazolines From 12-diaminesmentioning

confidence: 99%

Recent Advances in the Synthesis of Imidazolines (2009–2020)

Mehedi

Tepe

2020

Adv Synth Catal

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Imidazoline is an important class of compounds found in numerous natural and pharmaceutical products. The compounds are also used as an intermediate in the synthesis of organic molecules. Moreover, chiral imidazolines are widely utilized as organocatalysts to synthesize various natural and synthetic organic compounds. In the past decade, there was an increase in interest in developing new methods to synthesize these imidazoline analogs. Both modification of the previously established methods and the development of new methods are carried out significantly. This review article highlights the progress of the synthesis of imidazoline scaffolds in the last few years (2009-present). The review also described the proposed mechanism illustrated in many of the reports.

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“…To confirm the main contribution to intermediate stability from heteroatoms, we attempted to use 4‐benzyl‐2‐bromodifluoromethyl‐1,3‐oxazoline18 ( 1 f ) as the substrate, and found that it was also effective under this cross‐coupling method, providing the desired gem ‐difluoromethylenated cross‐coupling twin molecules in moderate to good yields. However, the reaction required a temperature of 60 °C with a 1 f / 2 /Cu 0 molar ratio of 3:1:6.9.…”

Section: Resultsmentioning

confidence: 99%

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A facile one-pot synthesis of 2-fluoroalkyl 1,3-imidazolines and 1,3-oxazolines through imidoyl halide intermediates

Cited by 15 publications

References 31 publications

Nucleophile-Dependent Regioselective Reaction of (S)-4-Benzyl-2-Fluoroalkyl-1,3-Oxazolines

Nucleophile-Dependent Regioselective Reaction of (S)-4-Benzyl-2-Fluoroalkyl-1,3-Oxazolines

Recent Advances in the Synthesis of Imidazolines (2009–2020)

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