Straightforward convergent access to 2-arylated polysubstituted benzothiazoles

A modular access to 2,4 disubstituted benzothiazoles has been achieved though the intermediacy of 4-bromo-2-iodobenzothiazole. The difference in reactivity of both halogens was advantageously exploited to achieve sequential Suzuki-Miyaura cross-coupling giving access to a range of polyaromatic derivatives featuring a central benzothiazole core.

• Publication year

  2019

• Venue

  Tetrahedron

• Publication date

  2019-12-05

• Fields of study

  Chemistry

• Identifiers
  DOI 10.3762/bxiv.2019.152.v1
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar

• No claims are published for this paper.

• No concepts are published for this paper.

• Excited-state intramolecular proton transfer (ESIPT) emitters based on a 2-(2′-hydroxybenzofuranyl)benzoxazole (HBBO) scaffold functionalised with oligo(ethylene glycol) (OEG) chains

  2019cited by this paper
• Natural Born Laser Dyes: Excited-State Intramolecular Proton Transfer (ESIPT) Emitters and Their Use in Random Lasing Studies

  2019cited by this paper
• White-light generation from all-solution-processed OLEDs using a benzothiazole-salophen derivative reactive to the ESIPT process.

  2019cited by this paper
• Direct Transformation of Arylamines to Aryl Halides via Sodium Nitrite and N-Halosuccinimide.

  2018cited by this paper
• Selective mono N-methylation of anilines with methanol catalyzed by rhenium complexes: An experimental and theoretical study

  2018cited by this paper
• Contemporary progress in the synthesis and reactions of 2-aminobenzothiazole: a review

  2018cited by this paper
• Ethynyl-Tolyl Extended 2-(2′-Hydroxyphenyl)benzoxazole Dyes: Solution and Solid-state Excited-State Intramolecular Proton Transfer (ESIPT) Emitters

  2018cited by this paper
• On the Fine-Tuning of the Excited-State Intramolecular Proton Transfer (ESIPT) Process in 2-(2'-Hydroxybenzofuran)benzazole (HBBX) Dyes.

  2017cited by this paper
• N‐Methyl‐Benzothiazolium Salts as Carbon Lewis Acids for Si−H σ‐Bond Activation and Catalytic (De)hydrosilylation

  2016cited by this paper
• A novel excited-state intramolecular proton transfer (ESIPT) dye with unique near-IR keto emission and its application in detection of hydrogen sulfide.

  2015cited by this paper
• Recent Advances in the Chemistry and Biology of Benzothiazoles

  2015cited by this paper
• A comprehensive review in current developments of benzothiazole-based molecules in medicinal chemistry.

  2015cited by this paper
• Thioflavin-based molecular probes for application in Alzheimer's disease: from in silico to in vitro models.

  2015cited by this paper
• A water-soluble ESIPT fluorescent probe with high quantum yield and red emission for ratiometric detection of inorganic and organic palladium.

  2015cited by this paper
• Organotrifluoroborates: Another Branch of the Mighty Oak.

  2015cited by this paper
• Strongly phosphorescent platinum(II) complexes supported by tetradentate benzazole-containing ligands

  2015cited by this paper
• Selection of boron reagents for Suzuki-Miyaura coupling.

  2014cited by this paper
• Recent advances in the synthesis of 2-substituted benzothiazoles: a review

  2014cited by this paper
• The benzazole scaffold: a SWAT to combat Alzheimer's disease.

  2013cited by this paper
• QSAR modeling of synthesized 3-(1,3-benzothiazol-2-yl) 2-phenyl quinazolin-4(3H)-ones as potent antibacterial agents

  2012cited by this paper
• Structural requirement(s) of N-phenylthioureas and benzaldehyde thiosemicarbazones as inhibitors of melanogenesis in melanoma B 16 cells.

  2010cited by this paper
• On the properties of new benzothiazole derivatives for organic light emitting diodes (OLEDs): A comprehensive theoretical study

  2010cited by this paper
• Design, selection, and characterization of thioflavin-based intercalation compounds with metal chelating properties for application in Alzheimer's disease.

  2009cited by this paper
• Naturally Occurring Nitrogen–Sulfur Compounds. The Benzothiazole Alkaloids

  2009cited by this paper
• Scope of the Suzuki-Miyaura cross-coupling reactions of potassium heteroaryltrifluoroborates.

  2009cited by this paper
• Improved Procedures for the Preparation of Cycloalkyl-, Arylalkyl-, and Arylthioureas

  1988cited by this paper
• Einwirkung von Brom auf aromatische Thioharnstoffe

  1903cited by this paper
• Einwirkung von Halogenen auf Thioharnstoffe

  1901cited by this paper

• The Application Research on Cu-Al/Sba-15 Bimetallic Synergistic Effect in the C-X Bond Sequential Assembly

  2022cites this paper
• Chiral Benzothiazole Monofluoroborate Featuring Chiroptical and Oxygen-Sensitizing Properties: Synthesis and Photophysical Studies.

  2021cites this paper
• Current advances in the synthetic strategies of 2-arylbenzothiazole

  2020cites this paper