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Updated: Jun 7, 2025

Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
Ag-Catalyzed Cyclization-Intermolecular Sulfinyl Group Transfer Cascade Reactions Enabling Enantioselective Synthesis
Itaru Nakamura1,2,3, Keiryo Kubota2, Hiroki Tashiro2
1Institute for Excellence in Higher Education, Tohoku University, 41 Kawauchi, Aoba-ku, Sendai, 980-8576, Japan.
Abstract:
N-Sulfinylimines derived from ortho-alkynylbenzaldehydes were efficiently converted into the corresponding 4-sulfinylisoquinolines in good to excellent yields. The reaction proceeds via cyclization followed by intermolecular migration of the sulfinyl group from the nitrogen atom to the silver-bound carbon of the resulting cyclized vinylsilver intermediate with the aid of either a counteranion or a nucleophilic species. Moreover, the Ag-catalyzed reaction in the presence of quinidine acetate as a chiral nucleophilic cocatalyst yielded chiral isoquinolines with high enantioselectivities through a dynamic kinetic asymmetric transformation (DYKAT).
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