Sc(OTf)₃-Mediated [4 + 2] Annulations of N-Carbonyl Aryldiazenes with Cyclopentadiene to Construct Cinnoline Derivatives: Azo-Povarov Reaction.

ABSTRACT: We disclose the first accomplishment of the azo-Povarov reaction involving Sc(OTf)₃-catalyzed [4 + 2] annulations of N-carbonyl aryldiazenes with cyclopentadiene in chloroform, in which N-carbonyl aryldiazenes act as 4π-electron donors. Hence, this protocol offers a rapid access to an array of cinnoline derivatives in moderate to good yields for substrates over a wide scope. The synthetic potential of the protocol was achieved by the gram-scale reaction and further derivatization of the obtained polycyclic product.

SUBMITTER: Jimenez-Aberasturi X 

PROVIDER: S-EPMC9447289 | biostudies-literature | 2022 Sep

REPOSITORIES: biostudies-literature