Abstract
The LDA-mediated reaction of 4-methyl-1-phenylquinolone and 3-methyl-2-(methylthio)benzothiazolium tosylate proceeds differently depending on the amount of LDA used. With about 1 eq. LDA, the known condensation reaction takes place, and the expected benzothiazolic derivative forms. However, when 2 eq. LDA or more is used, a new reaction occurs by an interaction of the condensation product with an excess of LDA and results in cleavage of the C–S bond in the benzothiazole moiety along with the formation of the other C–S bond in the quinolone moiety to give the 2-aminothienoquinolone derivative.
Acknowledgements
The authors are grateful to Dr. Vered Marks for 1H and 13C NMR spectra measurements and Dr. Mariia Kaidash for the measurements of mass-spectra.
Disclosure statement
No potential conflict of interest was reported by the author(s).