Convenient Preparation of Halo-1,3-thiazoles: Important Building Blocks for Materials and Pharmaceutical Synthesis
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Convenient, scalable and high-yielding approaches to 2,5- and 2,4-dibromo-1,3-thiazole are reported that offer significant improvements over previously reported approaches. 2,5-Dibromo-1,3-thiazole was generated in two steps from commercially inexpensive 2-amino-1,3-thiazole, whereas 2,4-dibromo-1,3-thiazole was generated in a single step from commercially inexpensive 1,3-thiazolidine-2,4-dione. As part of this study, convenient approaches to 2-bromo- and 2-iodo-1,3-thiazole were also developed.Keywords:
Thiazole
Thiazolidine
The new Z-5-arylmethylene-4-thioxo-thiazolidine derivatives have been synthesized by condensation of ω -(4-formylphenoxy)acetophenone derivatives with 4-thioxo-thiazolidine derivatives, in good yields. The cycloaddition of the newly synthesized compounds to N-arylmaleimides, N-phenyl-1,2,4-triazole-3,5-dione, ethyl acrylate and ω -nitrostyrene has been studied. Under thermal reaction conditions [4 + 2] cycloaddition proceeds with complete site- and regioselectivity to yield the new fused thiopyrano[2,3-d]thiazole derivatives.
Thiazolidine
Thiazole
Acetophenone
Ethyl acrylate
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Abstract For Abstract see ChemInform Abstract in Full Text.
Thiazole
Thiazolidine
Conjugate
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Simple, versatile, and catalyst-free synthetic methods for β-keto dithiocarbamates, thiazolidine-2-thiones, and thiazole-2-thiones via the multicomponent reaction of CS2, amines, and sulfoxonium ylides have been described. The β-keto sulfoxonium ylides furnished β-keto dithiocarbamates in the presence of CS2 and secondary amines, whereas primary amines afforded thiazolidine-2-thiones or thiazole-2-thiones after dehydration in an acidic environment. With simple procedures, the reaction has a wide substrate scope and excellent functional group tolerance.
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Abstract Several new thiazoles ( 3–7 ), thiazolylpyrazole carbonitrile ( 10 , 11 ), and Thiazolidine sulfonamido conjugate derivatives ( 19–26 ) were prepared starting with p-Piperidinesulfonylacetophenones ( 1 , 2 ). The structure of these compounds was elucidated on the bases of elemental analysis, IR, PMR, and mass spectra. The antimicrobial activities of some selected compounds are also reported. Keywords: p-Piperidinesulfonylacetophenonesthiazolethiazolidine-containing piperidine sulfonamidethiazolylpyrazol
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Thiazole
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Piperidine
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Thiazolidine
Thiazole
Amide
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Thiazole
Benzothiazole
Thiazolidine
Thiazoline
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Abstract A single crystalline enantiomer of 2‐(2‐thioxothiazolidin‐3‐yl)thiazole 5 has been isolated as the major product of the pyrolysis of 3‐(2‐thiazolin‐2‐yl)thiazolidine‐2‐thione 3 (n = 1); the latter isolated as the sole product of the reaction between thiazolidine‐2‐thione 2 (n = 1) and diethyl azodicarboxylate (DEAD) in benzene.
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Diethyl azodicarboxylate
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The pharmacological activities of thiazole and pyrazole moieties as antimicrobial and anticancer agents have been thoroughly described in many literature reviews. In this study, a convenient synthesis of novel pyrazolo[5,1-b]thiazole-based heterocycles was carried out. The synthesized compounds were characterized by IR, 1H and 13C NMR spectroscopy and mass spectrometry. Some selected examples were screened and evaluated for their antimicrobial and anticancer activities and showed promising results. These products could serve as leading compounds in the future design of new drug molecules.
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Pyrazole
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Convenient, scalable and high-yielding approaches to 2,5- and 2,4-dibromo-1,3-thiazole are reported that offer significant improvements over previously reported approaches. 2,5-Dibromo-1,3-thiazole was generated in two steps from commercially inexpensive 2-amino-1,3-thiazole, whereas 2,4-dibromo-1,3-thiazole was generated in a single step from commercially inexpensive 1,3-thiazolidine-2,4-dione. As part of this study, convenient approaches to 2-bromo- and 2-iodo-1,3-thiazole were also developed.
Thiazole
Thiazolidine
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The arylidene derivatives (1) of 3-phenyl-1,3-thiazolidine-2,4-dithione undergo 1,4-cycloaddition reaction with acrylonitrile, ethyl acrylate, ω-nitrostyrene, styrylethyl ketone and N-arylmaleimides leading to substituted tetrahydrothiopyrano-7 H[2,3-d]thiazole-2-thiones (2) and (3). The bactericidal and fungicidal activities of the new products were tested.
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Thiazolidine
Ethyl acrylate
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