Formation of reagent-selective products from 2-(4,5-dihydrothi- azol-2-ylthio)-1-arylethanone with different nucleophiles

Saravanan, Sivaperuman; Mohan, P.; Muthusubramanian, Shanmugam

doi:10.1080/17415993.2010.533772

Cited by 4 publications

(4 citation statements)

References 22 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[33] Another direct access to unsubstituted aroyl-S,N-ketene acetals is granted by using 2-(4,5-dihydrothiazol-2-ylthio)-1arylethanone with bromo acetophenone alongside different diamino compounds in mediocre to excellent yields (Scheme 2, B, right). [34] A focus of this review article lies on aroyl-S,N-ketene acetals bearing a benzothiazole moiety, which mostly date back to the 1970s or earlier, being left in a slumber for nearly fifty years.…”

Section: Approaches To Benzo Anellated Aroyl-sn-ketene Acetalsmentioning

confidence: 99%

“… Aroyl‐ S , N ‐ketene acetal synthesis starting from acetophenone and carbon disulfide ( A ), [30] and different approaches to aroyl‐ S , N ‐ketene actals with no substituents at the thiazole moiety starting from dithiotic acid esters and aziridine [31] or 2‐aminoethane‐1‐thiol [32,33] as well as from 2‐(4,5‐dihydrothiazol‐2‐ylthio)‐1‐arylethanone ( B ) [34] …”

Section: Synthetic Approaches To Aroyl‐sn‐ketene Acetalsmentioning

confidence: 99%

“…Another direct access to unsubstituted aroyl‐ S , N ‐ketene acetals is granted by using 2‐(4,5‐dihydrothiazol‐2‐ylthio)‐1‐arylethanone with bromo acetophenone alongside different diamino compounds in mediocre to excellent yields (Scheme 2, B , right) [34] …”

Section: Synthetic Approaches To Aroyl‐sn‐ketene Acetalsmentioning

confidence: 99%

See 2 more Smart Citations

Aroyl‐S,N‐Ketene Acetals: Luminous Renaissance of a Class of Heterocyclic Compounds

Biesen,

Müller

2023

Chemistry A European J

View full text Add to dashboard Cite

Aroyl‐S,N‐ketene acetals represent a peculiar class of heterocyclic merocyanines, compounds bearing pronounced and rather short dipoles with great push‐pull characteristics that define their rich properties. They are accessible via a wide array of synthetic concepts and procedures, ranging from addition‐elimination and condensation procedures up to rearrangement and metal‐mediated reactions. With our work from 2020, aroyl‐S,N‐ketene acetals have been identified as powerful and promising dyes with pronounced and vastly tunable solid‐state emission and aggregation‐induced emission properties. One characteristic trademark of this class of dye molecules is the level of control that could be exerted, and which was thoroughly explored. Based on these results, the field was opened to extend the system to bi‐ and multichromophoric systems by the full toolkit of synthetic organic chemistry thus giving access to even more exciting properties and manifolded substance libraries capitalizing on the AIE properties. This review aims at outlining the reaction‐based principles that allow for a swift and facile access to aroyl‐S,N‐ketene acetals, their methodical and structural evolution and the plethora of fluorescence and aggregation properties.

show abstract

Section: Approaches To Benzo Anellated Aroyl-sn-ketene Acetalsmentioning

confidence: 99%

Section: Synthetic Approaches To Aroyl‐sn‐ketene Acetalsmentioning

confidence: 99%

See 1 more Smart Citation

Aroyl‐S,N‐Ketene Acetals: Luminous Renaissance of a Class of Heterocyclic Compounds

Biesen,

Müller

2023

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…-Biphenyl]-4-yl)-1,2,3-thiadiazole (3g). 26 The representative procedure was followed using N′-(1-([1,1′-biphenyl]-4-yl)-2bromoethylidene) benzohydrazide (1g) (0.2 mmol) and KSCN (0.4 mmol) as the substrate. Isolation by column chromatography (PE/ EtOAc: 10:1) yielded 3g (40 mg, 86%) as a yellow oil.…”

Section: -([11′mentioning

confidence: 99%

Perylenequinonoid-Catalyzed [4 + 1] and [4 + 2] Annulations of Azoalkenes: Photocatalytic Access to 1,2,3-Thiadiazole/1,4,5,6-Tetrahydropyridazine Derivatives

Zhang

Cao

et al. 2019

J. Org. Chem.

View full text Add to dashboard Cite

Nitrogen-containing heterocycles are especially considered “privileged” structural scaffolds for the development of new drugs. However, traditional methods of organic synthesis are mainly based on thermal cycloaddition reaction; thus, the exploration of new strategies for the rapid assembly of N-heterocycles under mild conditions is highly desirable. Here, we developed a new method that visible light along with 1 mol % cercosporin, which is one of the perylenequinonoid pigments with excellent properties of photosensitization and can be easily produced by a new isolated endophytic fungus Cercospora sp. JNU001 strain with high yield through microbial fermentation, catalyzes the synthesis of 1,2,3-thiadiazoles and 1,4,5,6-tetrahydropyridazines by a photocatalytic process with good regioselectivity and broad functional-group compatibility under mild conditions. Thus, a bridge between microbial fermentation and organic photocatalysis for the construction of nitrogen-containing heterocycles was set up in a sustainable, environmentally friendly manner.

show abstract

2-Ylidene-1,3-thiazolidines and their nonhydrogenated analogs: methods of synthesis and chemical properties

Litvinchuk

Bentya

Slyvka

et al. 2020

Chem Heterocycl Comp

View full text Add to dashboard Cite

Formation of reagent-selective products from 2-(4,5-dihydrothi- azol-2-ylthio)-1-arylethanone with different nucleophiles

Cited by 4 publications

References 22 publications

Aroyl‐S,N‐Ketene Acetals: Luminous Renaissance of a Class of Heterocyclic Compounds

Aroyl‐S,N‐Ketene Acetals: Luminous Renaissance of a Class of Heterocyclic Compounds

Perylenequinonoid-Catalyzed [4 + 1] and [4 + 2] Annulations of Azoalkenes: Photocatalytic Access to 1,2,3-Thiadiazole/1,4,5,6-Tetrahydropyridazine Derivatives

2-Ylidene-1,3-thiazolidines and their nonhydrogenated analogs: methods of synthesis and chemical properties

Contact Info

Product

Resources

About