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Pregled bibliografske jedinice broj: 875240

Synthesis of 3–aryl 3–hydroxyisoindolinones by the Addition of Grignard and Organolithium Reagents to Phthalimides


Glavač, Danijel; Dokli, Irena; Gredičak, Matija
Synthesis of 3–aryl 3–hydroxyisoindolinones by the Addition of Grignard and Organolithium Reagents to Phthalimides // Current organic chemistry, 21 (2017), 14; 1335-1340 doi:10.2174/1385272821666170222100150 (međunarodna recenzija, članak, znanstveni)


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Naslov
Synthesis of 3–aryl 3–hydroxyisoindolinones by the Addition of Grignard and Organolithium Reagents to Phthalimides

Autori
Glavač, Danijel ; Dokli, Irena ; Gredičak, Matija

Izvornik
Current organic chemistry (1385-2728) 21 (2017), 14; 1335-1340

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
3–hydroxyisoindolinones, Grignard reaction, organolithium reaction, phthalimide, organometallic addition

Sažetak
The 3-substituted 3- hydroxyisoindolinone motif is common to a variety of compounds with potent biological activities. In recent years, they have also been increasingly used as substrates in various asymmetric transformations. Current methods for their preparation either do not tolerate wide range of functional groups, or yield 3– hydroxyisoindolinones as N–substituted products, which makes them inapplicable as substrates for the asymmetric transformations. Aim of this study was a detailed examination of the synthesis of 3–substituted 3– hydroxyisoindolinones comprising various functional groups and unsubstituted phthalimide nitrogen. Grignard and organolithium reagents were employed as nucleophiles for the synthesis of 3–substituted 3–hydroxyisoindolinones under various reaction conditions. Phenyl substituents with electron donating groups are easily introduced by employing a Grignard reaction, while electron– poor arenes require a lithium exchange or direct lithiation strategy. The protocols are tolerant of various functional groups on the nucleophile, and a wide range of 3–hydroxyisoindolinones were afforded in good to excellent yields. Conclusion: Simple and inexpensive method for the synthesis of 3-substituted 3-hydroxyisoindolinone has been developed. By tweaking the reaction conditions, described protocols are tolerant of a wide range of functional groups, and yield 3–substituted isoindolinone alcohols with unsubstituted phthalimide nitrogen.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Ustanove:
Institut "Ruđer Bošković", Zagreb

Profili:

Avatar Url Matija Gredičak (autor)

Avatar Url Irena Dokli (autor)

Avatar Url Danijel Glavač (autor)

Citiraj ovu publikaciju

Glavač, Danijel; Dokli, Irena; Gredičak, Matija
Synthesis of 3–aryl 3–hydroxyisoindolinones by the Addition of Grignard and Organolithium Reagents to Phthalimides // Current organic chemistry, 21 (2017), 14; 1335-1340 doi:10.2174/1385272821666170222100150 (međunarodna recenzija, članak, znanstveni)
Glavač, D., Dokli, I. & Gredičak, M. (2017) Synthesis of 3–aryl 3–hydroxyisoindolinones by the Addition of Grignard and Organolithium Reagents to Phthalimides. Current organic chemistry, 21 (14), 1335-1340 doi:10.2174/1385272821666170222100150.
@article{article, year = {2017}, pages = {1335-1340}, DOI = {10.2174/1385272821666170222100150}, keywords = {3–hydroxyisoindolinones, Grignard reaction, organolithium reaction, phthalimide, organometallic addition}, journal = {Current organic chemistry}, doi = {10.2174/1385272821666170222100150}, volume = {21}, number = {14}, issn = {1385-2728}, title = {Synthesis of 3–aryl 3–hydroxyisoindolinones by the Addition of Grignard and Organolithium Reagents to Phthalimides}, keyword = {3–hydroxyisoindolinones, Grignard reaction, organolithium reaction, phthalimide, organometallic addition} }
@article{article, year = {2017}, pages = {1335-1340}, DOI = {10.2174/1385272821666170222100150}, keywords = {3–hydroxyisoindolinones, Grignard reaction, organolithium reaction, phthalimide, organometallic addition}, journal = {Current organic chemistry}, doi = {10.2174/1385272821666170222100150}, volume = {21}, number = {14}, issn = {1385-2728}, title = {Synthesis of 3–aryl 3–hydroxyisoindolinones by the Addition of Grignard and Organolithium Reagents to Phthalimides}, keyword = {3–hydroxyisoindolinones, Grignard reaction, organolithium reaction, phthalimide, organometallic addition} }

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus


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