Solvent effect in the Wollgerodt-Kindler reaction

✍ Scribed by Martial R. Kanyonyo; Huseyin Ucar; Majed Isa; Pascal Carato; Daniel Lesieur; Pierre Renard; Jacques H. Poupaert

• Publisher: Wiley (John Wiley & Sons)
• Year: 2010
• Weight: 382 KB
• Volume: 105
• Category: Article
• ISSN: 0037-9646
• DOI: 10.1002/bscb.19961050105

✦ Synopsis

The Willgerodt-Kindler reaction was studied on three different model compounds (4-bromo benzaldehyde, 4-fluorobenzaldehyde, 4-methoxyacetophenone) with particular emphasis on the influence of the solvent on the yield of the reaction. Best conditions involved the use of polar aprotic solvents such as DMF. This finding was applied to the Willgerodt-Kindler reaction of two difficult s u b s t r a t e s , i. e. 3 -rn e t h y I-6form y I-2 ( 3 H)be nzox a z o I i n on e a n d 3 -me thy I-6 -f o r m y i -2 ( 3 H) - benzothiazolinone with various secondary amines.