Synthesis of 2-Aryl-1-pyrrolines from Arylnitriles

Keppens, M.; Dekimpe, N.; Fonck, Gwendolien

doi:10.1080/00397919608004614

Cited by 5 publications

(1 citation statement)

References 17 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Instead, the novel ferrocenophane 17 was obtained as the only isolable ferrocene-containing product from the reaction mixture (Scheme ). It has been reported in the literature that Grignard reagent BrMgCH 2 CH 2 CH 2 N(SiMe 2 CH 2 ) 2 can be generated successfully from the reaction of bromide 15 with magnesium metal . Previous reports have also indicated that the cyclic disilyl protecting group was stable to organolithium reagents .…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Characterization of Water-Soluble Cationic and Anionic Polyferrocenylsilane Polyelectrolytes

2002

View full text Add to dashboard Cite

Convenient routes to a range of water-soluble polyferrocenylsilane polyelectrolytes are reported. Direct reaction of the protected aminopropynyl reagent LiC⋮CCH2N(SiMe2CH2)2 (8) with the substitutionally labile ring-opened polymer [fcSiMeCl] n (3) (fc = Fe(η−C5H4)2), which is generated via Pt-catalyzed ring-opening polymerization of the silicon-bridged [1]ferrocenophane fcSiMeCl (6), afforded the polymer [fcSiMe{C⋮CCH2N(SiMe2CH2)2}] n (10). Polymer 10 was also obtained via ring-opening polymerization of the [1]ferrocenophane fcSiMe{C⋮CCH2N(SiMe2CH2)2} (9) prepared from the reaction of the lithium salt 8 and the substitutionally labile [1]ferrocenophane 6, which is readily accessible via the reaction of fcLi2·TMEDA with MeSiCl3. Deprotection of 10 was readily achieved using THF/MeOH to yield [fcSiMe(C⋮CCH2NH2)] n (11), which was conveniently reduced with hydrazine to the analogous aminopropyl polymer [fcSiMe(CH2CH2CH2NH2)] n (12). Treatment of polyferrocenylsilanes 11 and 12 with HCl generated the water-soluble cationic polyelectrolytes [fcSiMe(C⋮CCH2NH3Cl)] n (13) and [fcSiMe(CH2CH2CH2NH3Cl)] n (14), respectively. Cationic polyferrocenylsilanes 13 and 14 were obtained in three steps from polymer 3 with an overall yield of 40−50%. An unexpected rearrangement process took place during the lithiation of the protected aminopropyl bromide Br(CH2)3N(SiMe2CH2)2 (15) and a reaction of the resulting lithium salt with 6 yielded the novel [1]ferrocenophane fcSiMe{N(CH2)3SiMe2(CH2)2SiMe2} (17) with a rearranged, and ring-expanded, cyclic silylamino substituent. Species 17 underwent thermal ring-opening polymerization to afford [fcSiMe{N(CH2)3SiMe2(CH2)2SiMe2}] n (18). Treatment of polymer 10 with 1,3-propane sultone afforded the anionic polyelectrolyte [fcSiMe{C⋮CCH2N(CH2CH2CH2SO3Na)2}] n (19). Polymer 19 was readily reduced with hydrazine to give [fcSiMe{CH2CH2CH2NH(CH2CH2CH2SO3)(CH2CH2CH2SO3Na)}] n (20) bearing saturated side chains; subsequent deprotonation yielded the anionic polyelectrolyte [fcSiMe{CH2CH2CH2N(CH2CH2CH2SO3Na)2}] n (21). All three anionic polyelectrolytes 19−21 were obtained in 2−3 steps from 3 with 60−75% overall yields. The polyferrocenylsilane polyelectrolytes 13, 14, and 19−21 were readily soluble in water, making them potentially useful materials for a range of applications.

show abstract

Section: Resultsmentioning

confidence: 99%

Synthesis and Characterization of Water-Soluble Cationic and Anionic Polyferrocenylsilane Polyelectrolytes

2002

View full text Add to dashboard Cite

show abstract

ChemInform Abstract: Synthesis of 2‐Aryl‐1‐pyrrolines from Arylnitriles.

1996

View full text Add to dashboard Cite

show abstract

Synthesis of N‐Aryl Formyl Pyrrole from γ‐Lactam Derivatives: A Highlight

Barman

2018

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

Pyrrole containing analogs are considered as a potential source of biologically active compounds and have significant set of advantageous properties and are found in many natural products. A number of methods have been reported till now to synthesize pyrrole and pyrrole containing analogs. This review article outlines highlight the recent progresses in pyrrole synthesis from γ‐lactam derivatives.

show abstract

Synthesis of 2-Aryl-1-pyrrolines from Arylnitriles

Cited by 5 publications

References 17 publications

Synthesis and Characterization of Water-Soluble Cationic and Anionic Polyferrocenylsilane Polyelectrolytes

Synthesis and Characterization of Water-Soluble Cationic and Anionic Polyferrocenylsilane Polyelectrolytes

ChemInform Abstract: Synthesis of 2‐Aryl‐1‐pyrrolines from Arylnitriles.

Synthesis of N‐Aryl Formyl Pyrrole from γ‐Lactam Derivatives: A Highlight

Contact Info

Product

Resources

About