Preparation of 1,5-Disubstituted Pyrrolidin-2-ones

Katritzky, Alan R.; Mehta, S. M.; He, Hongwu; Cui, Xilin

doi:10.1021/jo000219w

Cited by 35 publications

(23 citation statements)

References 30 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The reaction of 2,5-dimethoxy-2,5-dihydrofuran 63, benzotriazole, and primary amines in refluxing AcOH gave 5-benzotriazolyl-1-substituted-pyrrolidin-2-ones 64 in good yields, with strong preference for the benzotriazol-1-yl isomer (Scheme 20) [76]. Substitution of the benzotriazolyl moiety in 64 with nucleophiles gave 5-substituted 2-pyrrolidinones 65-67.…”

Section: Pyrrolidinonesmentioning

confidence: 99%

“…Treatment of intermediates 64 with 4 equiv. of trimethylallyl-or trimethyl(2-methylallyl)silane in the presence of a Lewis acid furnished 1-substituted-5-allylpyrrolidinones 65 (Scheme 21) [76].…”

Section: Pyrrolidinonesmentioning

confidence: 99%

“…The treatment of 64 in dry THF with triethylphosphite in the presence of zinc bromide produced diethyl 1-substituted-5-oxo-2-pyrrolidinylphosphonates 67 in moderate to good yields (Scheme 23) [76].…”

Section: Pyrrolidinonesmentioning

confidence: 99%

See 2 more Smart Citations

Benzotriazole-Mediated Synthesis of Nitrogen-Containing Heterocycles

Beagle

2015

Topics in Heterocyclic Chemistry

View full text Add to dashboard Cite

Application of benzotriazole methodology for the preparation of nitrogen-containing heterocyclic compounds is summarized in this review. The characteristic advantages of benzotriazole are first briefly considered followed by an overview of its use in the synthesis of heterocycles organized by the ring size. Finally, the use of benzotriazole in the synthesis of bicyclic systems is showcased in only selected examples.

show abstract

Section: Pyrrolidinonesmentioning

confidence: 99%

Section: Pyrrolidinonesmentioning

confidence: 99%

See 1 more Smart Citation

Benzotriazole-Mediated Synthesis of Nitrogen-Containing Heterocycles

Beagle

2015

Topics in Heterocyclic Chemistry

View full text Add to dashboard Cite

show abstract

“…1 Cotinine 2 is a metabolite of nico-tine and is found in tobacco, 2 it can cross the blood brain barrier and has interesting medicinal properties (Fig. 6 Katritzky et al 7 and Sun et al 6 have also reported on the importance of this calss of compound. 3 γ-Lactams with quaternary stereogenic centres at C5, such as dysibetaine 3, displays neuroexcitotoxine activity.…”

Section: Introductionmentioning

confidence: 99%

γ-Lactams and furan bispyrrolidines via iodine mediated cyclisation of homoallylamines

et al. 2015

View full text Add to dashboard Cite

1,3,5-Substituted pyrrolidin-2-ones were synthesised via an iodine mediated cyclisation of 3-methyl substituted homoallylamines in good to excellent yield, as mixtures of diastereoisomers. These were separable and their identity confirmed by techniques including single crystal X-ray diffraction. When 3-phenyl substituted homoallylamines were cyclised intriguing fused tricyclic motifs were obtained as C 2 -symmetric racemates, whose structures were also confirmed by techniques including single crystal X-ray diffraction analysis.

show abstract

“…Katritzky et al reported the synthesis of pyrrolyl-benzotriazoles by the Mannich condensation of o-phthalaldehyde and 2,5-dimethoxy-2,5-dihydrofuran with primary amines, 12) but this method was not effective for pyrroles, and the desired products were produced only in less than 10% yields. As a new approach, the oxidative C-H bond functionalization strategies of pyrroles [13][14][15][16][17][18][19][20][21][22] might be expected to be an attractive methodology for enabling rapid access to these molecules.…”

mentioning

confidence: 99%

Clean Synthesis of <i>N</i>-Pyrrolyl Azoles by Metal-Free Oxidative Cross-Coupling Using Recyclable Hypervalent Iodine Reagent

Ogawa

Koseki

Takahashi

et al. 2015

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

The facile and clean oxidative coupling reaction of pyrroles with azoles has been achieved using the recyclable hypervalent iodine(III) reagents having adamantane structures. These iodine(III) reagents could be recovered from the reaction mixtures by a simple solid-liquid separation, i.e., filtration, for reuse.Key words oxidative coupling; hypervalent iodine reagent; recycle; pyrrole; azole; C-N bond formationThe N-pyrrolyl azoles are important fragments in the molecules of biological systems or in many pharmaceuticals, insecticides, and functional materials, especially, fluorescent dyes. [1][2][3][4] In spite of this interest, the preparations of N-aryl azoles are severely restricted because the nitrogen heteroaromatics are sometimes not a good substrate to use in the traditional arylation methods such as the Ullmann coupling, [5][6][7][8][9][10][11] since the pyrrole-based metal and halide compounds are sometimes unstable. Katritzky et al. reported the synthesis of pyrrolyl-benzotriazoles by the Mannich condensation of o-phthalaldehyde and 2,5-dimethoxy-2,5-dihydrofuran with primary amines, 12) but this method was not effective for pyrroles, and the desired products were produced only in less than 10% yields. As a new approach, the oxidative C-H bond functionalization strategies of pyrroles [13][14][15][16][17][18][19][20][21][22] might be expected to be an attractive methodology for enabling rapid access to these molecules. Recently, we have developed a new hypervalent iodine-induced oxidative coupling of pyrroles at the N 1 -positions of the azoles. 23) In 2014, Chen and colleagues reported the oxidative coupling method of 1,2,3-triazoles with pyrroles using N-iodosuccinimide (NIS) as an oxidant, in which the reactions preferentially occurred at the N 2 -position of the 1,2,3-triazoles.24) However, these methods produced stoichiometric quantities of iodoarene or succinimide as a waste product after the reaction (Chart 1).Hypervalent iodine reagents have received much attention due to their mild oxidation abilities and low toxicity, easy handling, as alternatives to toxic heavy metal reagents. [25][26][27][28][29][30][31][32] For developing a new coupling for heteroaromatic compounds, we have been engaged in the study of the oxidative C-H bond arylations using hypervalent iodine reagents that utilize the new reactivities of the heteroaromatic iodonium intermediates. [33][34][35][36][37] As mentioned, we developed a hypervalent iodineinduced oxidative coupling of pyrroles at the N 1 -positions of the azoles.23) This new method is versatile in allowing the reactions under metal-free and mild conditions, and tolerates a diverse series of functionalities of the pyrroles and azole coupling partners. We envisioned that a recycling version of this oxidative coupling should become feasible and provide an eco-friendly synthetic method (Chart 2) because a number of recent studies have demonstrated the utility of the recyclable hypervalent iodine reagents. 38-40) Results and DiscussionThe use of recyclable hypervalent ...

show abstract

Preparation of 1,5-Disubstituted Pyrrolidin-2-ones

Cited by 35 publications

References 30 publications

Benzotriazole-Mediated Synthesis of Nitrogen-Containing Heterocycles

Benzotriazole-Mediated Synthesis of Nitrogen-Containing Heterocycles

γ-Lactams and furan bispyrrolidines via iodine mediated cyclisation of homoallylamines

Clean Synthesis of <i>N</i>-Pyrrolyl Azoles by Metal-Free Oxidative Cross-Coupling Using Recyclable Hypervalent Iodine Reagent

Contact Info

Product

Resources

About