Insight into the Willgerodt-Kindler Reaction of ω-Haloacetophenone Derivatives: Mechanistic Implication | Zendy

Urbain C. Kasséhin | Zendy; Fernand Gbaguidi | Zendy; Coco N. Kapanda | Zendy; Christopher R. McCurdy | Zendy; Jacques H. Poupaert | Zendy

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Insight into the Willgerodt-Kindler Reaction of ω-Haloacetophenone Derivatives: Mechanistic Implication

Author(s) -

Urbain C. Kasséhin,

Fernand Gbaguidi,

Coco N. Kapanda,

Christopher R. McCurdy,

Jacques H. Poupaert

Publication year - 2014

Publication title -

organic chemistry international

Language(s) - English

Resource type - Journals

eISSN - 2090-2018

pISSN - 2090-200X

DOI - 10.1155/2014/486540

Subject(s) - morpholine , chemistry , yield (engineering) , dimethylformamide , reagent , substrate (aquarium) , combinatorial chemistry , condensation reaction , solvent , condensation , organic chemistry , biochemical engineering , catalysis , engineering , materials science , thermodynamics , oceanography , physics , metallurgy , geology

This paper reports efforts aimed at tuning up the synthesis of a compound library centered on the general template 2-amino-1-phenyl-2-thioxoethanone taking the condensation of ω-haloacetophenone, octasulfur, and morpholine as pilot reaction. Considerations about atomic economy were found extremely precious in selecting the best starting halo-reagent. A one-pot practical method based on use of 2-bromo-1-phenylethanone as substrate and N,N-dimethylformamide as solvent can be easily scaled up to gram amounts (72% yield). Based on this synthetic approach, some more specific examples are reported

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