Synthesis, Reactivity and Stability of Aryl Halide Protecting Groups towards Di-Substituted Pyridines

Brian, Ptoton Mnangat; Musau, Peter

doi:10.22146/ijc.21177

Cited by 5 publications

(4 citation statements)

References 17 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Many electron-rich alkoxybenzyl halides are unstable or are only stable in solution. 26 We assume the decomposition noted in our sample of 12a was a consequence of an exothermic ring-alkylation polymerization with release of HBr.…”

Section: Scheme 5 Bradsher Route To 3-naphthothiophene Derivativesmentioning

confidence: 98%

Short Syntheses of 1-Substituted Dibenzothiophenes and 3-Substituted Naphthothiophenes

En¹,

Ek²,

Roberston³

et al. 2019

Preprint

View full text Add to dashboard Cite

The 1-substituted dibenzothiophene motif is an unusual substitution pattern. We demonstrate a simple one-pot preparation of 1-lithiodibenzothiophene via a cascade of two benzyne additions and conversion to the aldehyde, boronic ester, and iodide. This work avoids the use of precious metals or tert-butyllithium and is shorter than existing routes to these compounds. We also report an improved route to the isomeric 3-substituted naphthothiophene scaffold. These protocols will allow rapid access to families of these two related heteroacenes.

show abstract

Section: Scheme 5 Bradsher Route To 3-naphthothiophene Derivativesmentioning

confidence: 98%

Short Syntheses of 1-Substituted Dibenzothiophenes and 3-Substituted Naphthothiophenes

En¹,

Ek²,

Roberston³

et al. 2019

Preprint

View full text Add to dashboard Cite

show abstract

“…Many electron-rich alkoxybenzyl halides are unstable or are only stable in solution. 19 We assume the decomposition noted in our sample of 10a was a consequence of an exothermic ring-alkylation polymerization, undergoing autocatalysis with release of HBr. Due to this potential safety issue, we discontinued studies toward naphthothiophene 2a by this route.…”

Section: Scheme 3 Realized Bradsher Routes To Naphthothiophene and 3-bromonaphthothiophenementioning

confidence: 99%

Efficient Synthesis and Functionalization of 3-Bromo Naphtho[2,3b]thiophene

Burke

Welsh

Robertson³

et al. 2021

Preprint

View full text Add to dashboard Cite

Naphtho[2,3b]thiophene is a linear sulfur containing polycyclic aromatic hydrocarbon. Naphtho[2,3b]thiophene and its derivatives are commonly accessed by a Bradsher cyclization. Synthesis of the Bradsher cyclization substrate typically requires harsh conditions, including several oxidation state changes. Here we report an improved, multigram synthesis of 3-bromonaphtho[2,3b]thiophene, exploiting a copper-catalyzed cross coupling to prepare the Bradsher substrate in 3 steps from commercial materials while minimizing redox reactions. Modification of the naphthothiophene scaffold in the 3-position has not previously been reported. In this work, the 3-bromonaphthothiophene is further functionalized via lithium-halogen exchange, with the key finding being a specific order of addition in lithiation is required to avoid undesired rearrangement reactions. A small yet versatile set of derivatives, including a naphthothiophene-containing chiral amine are prepared.

show abstract

“…N-containing heterocycles show a vast abundance of numerous natural products and several biologically active pharmaceuticals. Among the all heteroaromatic compounds, polysubstituted pyridines are unrivaled and also considered as "privileged medicinal scaffolds" because they are partial structures of many natural products, pharmaceuticals, and synthetic organic moieties [16][17][18][19][20][21].…”

Section: Introductionmentioning

confidence: 99%

One-Pot-Multicomponent Synthesis of 2,6-Diamino-4-arylpyridine-3,5-dicarbonitrile Derivatives Using Nanomagnetic Fe3O4@SiO2@ZnCl2

et al. 2018

View full text Add to dashboard Cite

Nanomagnetic Fe3O4@SiO2@ZnCl2 was used as a simple, cost-effective, and reusable heterogeneous catalyst for the synthesis of 2,6-diamino-4-arylpyridine-3,5-dicarbonitriles by a one-pot-three-component condensation reaction of malononitrile, ammonium acetate, and aldehydes under solvent-free conditions at 110 °C. Simple and mild reaction conditions, facile preparation of the catalyst, the use of a cheap catalyst and easy workup and isolation are notable features of this method. ABSTRAKNanomagnetik Fe3O4@SiO2@ZnCl2 digunakan sebagai katalis sederhana, hemat biaya, dan merupakan katalis heterogen yang dapat digunakan kembali untuk sintesis 2,6-diamino-4-arilpiridin-3,5-dikarbonitril melalui reaksi kondensasi tiga komponen one-pot antara malononitril, amonium asetat, dan aldehida dengan kondisi tanpa pelarut pada temperatur 110 °C. Kondisi reaksi yang sederhana dan ringan, persiapan katalis yang mudah, penggunaan katalis yang murah dan mudah dilakukan serta mudah diisolasi adalah aspek yang penting dari metode ini.

show abstract

Synthesis, Reactivity and Stability of Aryl Halide Protecting Groups towards Di-Substituted Pyridines

Cited by 5 publications

References 17 publications

Short Syntheses of 1-Substituted Dibenzothiophenes and 3-Substituted Naphthothiophenes

Short Syntheses of 1-Substituted Dibenzothiophenes and 3-Substituted Naphthothiophenes

Efficient Synthesis and Functionalization of 3-Bromo Naphtho[2,3b]thiophene

One-Pot-Multicomponent Synthesis of 2,6-Diamino-4-arylpyridine-3,5-dicarbonitrile Derivatives Using Nanomagnetic Fe<sub>3</sub>O<sub>4</sub>@SiO<sub>2</sub>@ZnCl<sub>2</sub>

Contact Info

Product

Resources

About