Tetrahedron
Tetrahedron
5 years ago

Cascade annulations of aryldiazonium salts, nitriles and halo-alkynes leading to 3-haloquinolines

Cascade annulations of aryldiazonium salts, nitriles and halo-alkynes leading to 3-haloquinolines
A regiospecific access to 3-haloquinolines has been developed via a three-component annulation of aryldiazonium salts, nitriles and haloalkynes. This reaction proceeds through an initial formation of reactive nitrilium ion and further cascade annulation with haloalkynes. This method provides a straightforward access to a diverse array of functionalized quinolones (28 examples) under mild conditions and exhibits broad functional group tolerance. Applications of this method in a gram scale reaction and a formal synthesis of Pitavastatin are illustrated.

Publisher URL: www.sciencedirect.com/science

DOI: S004040201730594X

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