Chemistry
Heterocyclic Building Blocks
Thiazoles
5-phenylthiazole
Electrophilic Aromatic Substitution (EAS): 5-Phenylthiazole can undergo EAS reactions, where an electrophile substitutes a hydrogen atom on the phenyl ring. Common electrophiles include nitration (HNO3/H2SO4), sulfonation (H2SO4), halogenation (e.g., Br2/FeBr3), and Friedel-Crafts acylation/alkylation.
Nucleophilic Aromatic Substitution (SNAr): The thiazole ring can also undergo SNAr reactions, where nucleophiles displace a leaving group. This reaction can be utilized for functionalization of the thiazole ring.
Reduction: 5-Phenylthiazole can be reduced using reducing agents like lithium aluminum hydride (LiAlH4) or sodium borohydride (NaBH4) to yield the corresponding dihydrothiazole.
Oxidation: Oxidizing agents like potassium permanganate (KMnO4) or chromic acid (H2CrO4) can oxidize thiazoles to produce thiazole derivatives.
Alkylation and Acylation: The nitrogen atom in the thiazole ring can be alkylated or acylated using suitable alkyl or acyl halides and a base, resulting in N-alkyl or N-acyl derivatives.
Heterocyclization: 5-Phenylthiazole can be used as a starting material in the synthesis of other heterocyclic compounds through various cyclization reactions.
Nucleophilic Addition: The nitrogen and sulfur atoms in the thiazole ring can participate in nucleophilic addition reactions with appropriate electrophiles, leading to functionalized products.
Cross-Coupling Reactions: 5-Phenylthiazole can participate in various cross-coupling reactions, such as Suzuki-Miyaura, Heck, or Stille couplings, to introduce different substituents onto the phenyl ring.
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(S)-1-(4-(4Methylthiazol-5-yl)phenyl)ethan-1-amine HCl
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2-Chloro-5-(4-fluorophenyl)thiazole-4-carboxylic acid
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2-Bromo-5-(4-fluorophenyl)thiazole-4-carboxylic acid
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(4-(4-Methylthiazol-5-yl)phenyl)methanamine hydrochloride
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(4-(4-Methylthiazol-5-yl)phenyl)methanamine
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2-Hydroxy-4-(4-methylthiazol-5-yl)benzonitrile
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N-(5-(4-Hydroxyphenyl)thiazol-2-yl)acetamide