Call us toll-free

A new synthesis of benzo[f]isoindole-4,9-diones by …

A new synthesis of benzo[f]isoindole-4,9-diones by radical alkylation and bromomethylation of 1,4-naphthoquinones.

Approximate price

Pages:

275 Words

$19,50

Synthesis of isoquinolines - Organic Chemistry Portal

Our design of responsive dyes use 1,3-bis(imino)isoindole as a central moiety. 1,3-bis(imino)isoindole derivatives are known to undergo intra molecular hydrogen bonding through their extended conjugation by benzannulation of aromatic rings and its pronounced fluorescence excitation properties. Platinum coupled 1,3-bis(imino)isoindole derivatives exhibit great photophysical and photoemission properties. In the present work, the design of the dyes utilized a 1,3-bis(aryl imino)isoindole (aryl: compound 1= 2-aminopyridine; compound 3= 4-butyl aniline) moiety and a strategically placed acyl fatty acid chain (R= −C8H17) to provide membrane stability (; compounds 1, 3). The aryl amines were selected based on their potential ability to form intra molecular hydrogen bonds within the molecule itself. We hypothesize that the benzannulation of pyridyl and isoindole rings in 1 will be influenced by the solvent polarity. A similar compound, 3, which lacks the extended conjugation by benzannulation of pyridyl and isoindole rings, was synthesized as a control compound. In order to investigate the compounds’ ability to undergo intra molecular hydrogen bonding in changing environments, dyes will be encapsulated within a phospholipids-coated nanoparticle and studied in vitro.

CHEMICALS & REAGENTS of UNITED QUANTUM …
Photo provided by Flickr

N2 - Poly(2,6-1H-benzo[f]isoindole-1,3(2H)-dione) (PBID), which was a self-condensable naphthalene-containing polyimide, was synthesized as precipitated crystals from 6-amino-3-(ethoxycarbonyl)-2-naphthoic acid and 7-amino-3-(ethoxycarbonyl)-2-naphthoic acid by using reaction-induced crystallization during solution polymerization. The obtained PBID crystals possessed high crystallinity, excellent thermal stability and chemical resistance. They neither exhibited Tg nor Tm under the decomposition temperature. The morphology of the PBID crystals depended on not only the polymerization conditions but also the isomeric structure of the monomer, and the wide variety of the morphology appeared such as rods, plates and lathes. The plate-like crystals had fine protuberances on the surface. Copolymerization of PBID and poly(4-phthalimide) were also examined.

Indole chemistry began to develop with the study of the dye indigo

“A New Synthesis of Benzo[f]isoindole-4,9-diones by Radical Alkylation and Bromomethylation of 1,4-naphthoquinones.”  28 (2009): 4882–4892.
Photo provided by Flickr

Our initial attempt to produce 1 and 3 by a solventless microwave assiated method was unsuccessful. Briefly, 3,6-Dioctyloxy-1,2-benzenedicarbonitrile (2) was added to the aryl amine (for compound 1: 2-aminopyridine; for compound 3: 4-butyl aniline) and calcium chloride followed by heating the mixture in a domestic microwave for 1–3 mins (). The formation of compound 1 was identified by 1H-NMR spectroscopy of the crude mixture. However, we were unsuccessful to isolate the desired compound from a complex mixture of side products. In case of 3, the product was never identified by the microwave route. In an alternative pathway, 1 and 3 were synthesized based on the nucleophilic addition of aryl amines to 1,2-benzenedicarbonitrile to form 1,3-bis(arylimino)isoindole derivatives () following a modified method. Briefly, 3,6-Dioctyloxy-1,2-benzenedicarbonitrile (2, 0.65 mmol), 2-aminopyridine (1.62 mmol) and 25 mg of CaCl2 was refluxed in 1-butanol under argon for 15h to produce 1 in 70% yield. In a similar fashion, compound 3 was synthesized from 4-butyl-aniline in 81% overall yield. The compounds were purified by repeated recrystallization to obtain fine needle-shaped orange crystals and characterized via1H-NMR and Mass Spectrometric analyses. The synthesized compounds were preserved at 4°C protecting from light and moisture. Interestingly, upon exposure to moisture, the 1,3-bis(arylimino)isoindole derivatives were found to undergo slow hydrolytic degradation as indicated by the appearance of O-phthalamide derivatives in 1H-NMR studies. ()

A synthetic methodology of preparing novel membrane stable, responsive dyes is revealed in this manuscript. 1,3-bis(arylimino)isoindole dyes were synthesized and their properties to undergo intramolecular hydrogen bonding was studied with fluorescence spectroscopy in varying solvent polarities. Based on the functional moieties, compound that is capable of hydrogen donor and acceptor interactions produces predominant photoexcitation in comparison to the responsive dyes that lack these functionalities. These dyes, by the virtue of the presence of long chain acyl groups could be incorporated stably within the phospholipids membrane of core-shell nanoparticles. Nanoparticle was ‘cracked’ to release the dye from a hydrophobic to a hydrophilic environment, A significant change in florescence intensity was then observed, indicating the direct change in effect of intramolecular hydrogen bonding based on solvent polarity changes. This unique study provided implications of many further applications towards nanomedicine and nano-biotechnology.

Indigo can be converted to isatin and then to oxindole

synthesis of isoxazole and 1,2,3-triazole isoindole derivatives via silver- and copper-catalyzed 1,3-dipolar cycloaddition reaction the cui- or ag2co3
Photo provided by Flickr

Poly(2,6-1H-benzo[f]isoindole-1,3(2H)-dione) (PBID), which was a self-condensable naphthalene-containing polyimide, was synthesized as precipitated crystals from 6-amino-3-(ethoxycarbonyl)-2-naphthoic acid and 7-amino-3-(ethoxycarbonyl)-2-naphthoic acid by using reaction-induced crystallization during solution polymerization. The obtained PBID crystals possessed high crystallinity, excellent thermal stability and chemical resistance. They neither exhibited Tg nor Tm under the decomposition temperature. The morphology of the PBID crystals depended on not only the polymerization conditions but also the isomeric structure of the monomer, and the wide variety of the morphology appeared such as rods, plates and lathes. The plate-like crystals had fine protuberances on the surface. Copolymerization of PBID and poly(4-phthalimide) were also examined.

AB - Poly(2,6-1H-benzo[f]isoindole-1,3(2H)-dione) (PBID), which was a self-condensable naphthalene-containing polyimide, was synthesized as precipitated crystals from 6-amino-3-(ethoxycarbonyl)-2-naphthoic acid and 7-amino-3-(ethoxycarbonyl)-2-naphthoic acid by using reaction-induced crystallization during solution polymerization. The obtained PBID crystals possessed high crystallinity, excellent thermal stability and chemical resistance. They neither exhibited Tg nor Tm under the decomposition temperature. The morphology of the PBID crystals depended on not only the polymerization conditions but also the isomeric structure of the monomer, and the wide variety of the morphology appeared such as rods, plates and lathes. The plate-like crystals had fine protuberances on the surface. Copolymerization of PBID and poly(4-phthalimide) were also examined.

Mohamed Othman, Pascal Pigeon, Bernard Decroix. Synthesis and reduction of thieno[2 `,3 `(3 `,2 ` or 3 `,4 `): 5,6]-azocino[2,1-a]isoindole-7,13-diones.
Photo provided by Flickr
Order now
  • General & Introductory Chemistry

    Categories: Synthesis of N-Heterocycles > benzo-fused N-Heterocycles > Synthesis of isoquinolines

  • Organic Letters - ACS Publications

    Recent Literature

  • Sigma-Aldrich Online Catalog Product List: C15 to C19

    Indole - Wikipedia

Order now
  • Kim

    "I have always been impressed by the quick turnaround and your thoroughness. Easily the most professional essay writing service on the web."

  • Paul

    "Your assistance and the first class service is much appreciated. My essay reads so well and without your help I'm sure I would have been marked down again on grammar and syntax."

  • Ellen

    "Thanks again for your excellent work with my assignments. No doubts you're true experts at what you do and very approachable."

  • Joyce

    "Very professional, cheap and friendly service. Thanks for writing two important essays for me, I wouldn't have written it myself because of the tight deadline."

  • Albert

    "Thanks for your cautious eye, attention to detail and overall superb service. Thanks to you, now I am confident that I can submit my term paper on time."

  • Mary

    "Thank you for the GREAT work you have done. Just wanted to tell that I'm very happy with my essay and will get back with more assignments soon."

Ready to tackle your homework?

Place an order