Synthesis 2017; 49(18): 4183-4190
DOI: 10.1055/s-0036-1588821
special topic
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed Intramolecular C–H Amination: A New Entry to Substituted Xanthine Derivatives

Maki Shimizu
School of Pharmacy and Pharmaceutical Sciences, Mukogawa Women’s University, 11-68, 9-Bancho, Koshien, Nishinomiya, Hyogo 663-8179, Japan   Email: inamoto@mukogawa-u.ac.jp
,
Noboru Hayama
School of Pharmacy and Pharmaceutical Sciences, Mukogawa Women’s University, 11-68, 9-Bancho, Koshien, Nishinomiya, Hyogo 663-8179, Japan   Email: inamoto@mukogawa-u.ac.jp
,
Tetsutaro Kimachi
School of Pharmacy and Pharmaceutical Sciences, Mukogawa Women’s University, 11-68, 9-Bancho, Koshien, Nishinomiya, Hyogo 663-8179, Japan   Email: inamoto@mukogawa-u.ac.jp
,
Kiyofumi Inamoto*
School of Pharmacy and Pharmaceutical Sciences, Mukogawa Women’s University, 11-68, 9-Bancho, Koshien, Nishinomiya, Hyogo 663-8179, Japan   Email: inamoto@mukogawa-u.ac.jp
› Author Affiliations
We gratefully acknowledge financial support by a Grant-in-Aid for Scientific Research (C) (No. 16K08187) from the Japan Society for the Promotion of Science.
Further Information

Publication History

Received: 19 March 2017

Accepted after revision: 10 April 2017

Publication Date:
09 May 2017 (online)


Published as part of the Special Topic Modern Cyclization Strategies in Synthesis

Abstract

Catalytic synthesis of xanthines was achieved in the presence of a copper catalyst. The process involves copper-catalyzed intramolecular C–H amination of benzamidines that possess a uracil moiety and produces variously substituted xanthines generally in good to high yields. This work introduces a new, facile approach to polysubstituted xanthine compounds.

Supporting Information