One-Pot Synthesis of 2,3-Dihydro-pyrrolopyridinones Using in Situ Generated Formimines

Deguest, Geoffrey; Devineau, Alice; Bischoff, Laurent; Fruit, Corinne; Marsais, Francis

doi:10.1021/ol062577c

Cited by 17 publications

(7 citation statements)

References 27 publications

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“…1 H NMR (400 MHz, CDCl 3 ): δ = 3.63 (s, 2 H, 5‐H), 2.68 (tt, J H,H 1 = 10.2, J H,H 2 = 3.8 Hz, 1 H, 1‐H), 1.83–1.88 (m, 2 H, 2/2′‐H), 1.72–1.78 (m, 2 H, 3/3′‐H), 1.60–1.67 (m, 1 H, 4‐H), 1.25–1.36 (m, 2 H, 3/3′‐H), 1.14–1.23 (m, 1 H, 4‐H),1.04–1.14 (m, 2 H, 2/2′‐H) ppm. Spectroscopic data are in agreement with those reported in the literature . A solution of N ‐cyclohexyl‐aminoacetonitrile thus prepared (5.50 g, 39.8 mmol) in 35 mL of Et 2 O (abs.)…”

Section: Methodssupporting

confidence: 87%

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Heterocycle Syntheses with Anionic N‐Heterocyclic Carbenes: Ring Transformations of Sydnone Imine Anions

et al. 2018

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Sydnone imines were deprotonated at the C4 position to give lithium‐stabilized anions, which proved to be stable for several months in solution. These anions are elements of the intersection of the substance classes of N‐heterocyclic carbenes and mesomeric betaines. They can be formulated as anionic N‐heterocyclic carbenes. The negative charge translates into high‐field shifts of the 13C NMR resonance frequencies of C4 in comparison to other NHCs. Similar to the chemistry of N‐heterocyclic carbenes, reactions with isocyanates and isothiocyanates gave 4‐(N‐carbamoyl)‐benzoylsydnone imines in trapping reactions. As a result of ring transformations involving the characteristic π‐architecture of the mesoionic framework, imidazolidine‐2,4‐dithiones, imidazolin‐2,4‐diones and 1,2,4‐triazol‐5‐ones were formed depending on the substitution pattern of the starting materials and the reaction conditions.

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Section: Methodssupporting

confidence: 87%

“…of ClCH 2 CN, 2.2 equiv. of K 2 CO 3 , MeCN, 20 h, reflux (79 %); B) 2.4 equiv. of amyl nitrite, Et 2 O, 20 h, room temp., then HCl(g), 1.5 h, room temp.…”

Section: Resultsmentioning

confidence: 99%

Heterocycle Syntheses with Anionic N‐Heterocyclic Carbenes: Ring Transformations of Sydnone Imine Anions

et al. 2018

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“…7 Nevertheless, the inclusion of a nitrogen atom in the aromatic ring could provide the opportunity to modulate both the pharmacodynamic and kinetic properties of pyrrolopyridines. 8 Several synthetically modified analogues of compound 1 have been prepared to evaluate their biological activity. 9 In connection with an ongoing project and with the goal of developing novel synthetic methodologies for gaining rapid access to new nitrogen heterocyclic compounds, we herein describe a rapid synthesis of a series of compounds 2 (Figure 1), which are aza-analogues of 1, based on an oxidative Ugi type reaction and the aza-Diels-Alder cycloaddition as post-condensation.…”

Section: Figure 1 Nuevamine and Its Aza-analoguementioning

confidence: 99%

One-Pot Synthesis of Nuevamine Aza-Analogues by Combined Use of an Oxidative Ugi Type Reaction and Aza-Diels–Alder Cycloaddition

Islas‐Jácome

Gutiérrez-Carrillo

González‐Zamora

2013

Synlett

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A rapid and efficient one-pot synthesis of a series of four novel nuevamine aza-analogues is described based on the oxidative Ugi-type reaction and aza-Diels-Alder reaction as post-functionalization. A simple IBX-mediated oxidation of a secondary amine followed by isonitrile α-addition and finally an aza-Diels-Alder cycloaddition provides the desired compounds in excellent overall yields considering the short reaction time, atom economy, and the molecular complexity of the final products. This protocol presents a highly attractive procedure for the rapid generation of fused polyheterocycles.

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“…[24][25][26][27][28] Previous studies in our laboratory confirmed that sulfomethylation is an efficient way to introduce the ASO 3 2 group into copolymers because it can give the copolymer remarkable antishearing ability, temperature resistance, and salt tolerance with simple operation and economic feasibility. 29,30 Hence, in this study, N,N-diallyl nicotinamide (DANA) was synthesized as described in the literature; 31,32 it was copolymerized with sodium acrylate (NaAA) and AM to obtain an AM/AA/ DANA copolymer. Furthermore, the ASO 3 2 group was used in AM/AA/DANA via sulfomethylation with the aim of improving the temperature tolerance and shear tolerance of the copolymer (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Modification of a nicotinic acid functionalized water‐soluble acrylamide sulfonate copolymer for chemically enhanced oil recovery

Gou

Liu

et al. 2013

J of Applied Polymer Sci

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N,N-Diallyl nicotinamide (DANA) and acrylic acid (AA) were used to react with acrylamide (AM) and synthesize a novel nicotinic acid functionalized water-soluble copolymer AM/AA/DANA by redox free-radical polymerization. Then, the acrylamide/sodium acrylamido methanesulfonate/acrylic acid/N,N-diallyl nicotinamide (AM/AMS/AA/DANA) was obtained by the introduction of the ASO 3 2 group into AM/AA/DANA after sulfomethylation. The optimal reaction conditions, such as the monomer ratio, initiator concentration, reaction temperature, and pH of the copolymerization or sulfomethylation, were investigated. Both AM/AA/ DANA and AM/AMS/AA/DANA were characterized by IR spectroscopy, 1 H-NMR, scanning electron microscopy, and intrinsic viscosity testing. We found that the AM/AMS/AA/DANA had a remarkable temperature tolerance (120 C, viscosity retention rate 5 39.8%),shear tolerance (1000 s 21 , viscosity retention rate 5 23.3%), and salt tolerance (10 g/L NaCl, 1.5 g/L MgCl 2 , 1.5 g/L CaCl 2 , viscosity retention rates 5 37.4, 27.5, and 21.6%). In addition, the result of the core flood test showed that the about 13.1% oil recovery could be enhanced by 2.0 g/L AM/AMS/AA/DANA at 70

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One-Pot Synthesis of 2,3-Dihydro-pyrrolopyridinones Using in Situ Generated Formimines

Cited by 17 publications

References 27 publications

Heterocycle Syntheses with Anionic N‐Heterocyclic Carbenes: Ring Transformations of Sydnone Imine Anions

Heterocycle Syntheses with Anionic N‐Heterocyclic Carbenes: Ring Transformations of Sydnone Imine Anions

One-Pot Synthesis of Nuevamine Aza-Analogues by Combined Use of an Oxidative Ugi Type Reaction and Aza-Diels–Alder Cycloaddition

Modification of a nicotinic acid functionalized water‐soluble acrylamide sulfonate copolymer for chemically enhanced oil recovery

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