Rhodium(ii)-catalyzed synthesis of 2-aminoquinoline derivatives from 2-quinolones and N-sulfonyl-1,2,3-triazoles

Herein, we disclose a rhodium(ii) catalyzed efficient and convenient method for the synthesis of 2-aminoquinoline derivatives from 2-quinolones and N-sulfonyl-1,2,3-triazoles. The reaction provides rapid access to a series of 2-aminoquinolines with moderate to excellent yields. The reaction proceeds via quinolone-hydroxyquinoline tautomerization/O-H insertion to a rhodium(ii)-aza vinyl carbene intermediate generated by denitrogenation of triazole followed by rearrangement to deliver the desired product. Furthermore, we demonstrated the iodine-mediated dealkylation of a 2-aminoquinoline derivative.

Automated summary

Here, we disclose an efficient and convenient method catalyzed by rhodium(ii) for the synthesis of 2-aminoquinoline derivatives from 2-quinolones and N-sulfonyl-1,2,3-triazoles. This method provides rapid access to 2-aminoquinolines with moderate to excellent yields, and the reaction proceeds through quinolone-hydroxyquinoline tautomerization/O-H insertion to a rhodium(ii)-aza vinyl carbene intermediate generated by denitrogenation of the triazole.