A copper-catalyzed direct synthesis of 2-(aminomethyl)indoles by catalytic domino reaction including multi-component coupling was developed, and is the first example of a three-component indole formation without producing salts as a byproduct. Based on this reaction, a copper-catalyzed synthesis of 3-(aminomethyl)isoquinoline was accomplished which represents an unprecedented isoquinoline synthesis through a four-component coupling reaction. Following these results, extensive application studies using one-pot palladium-, acid-, or base-promoted cyclization revealed that indole- or isoquinoline-fused polycyclic compounds can be readily synthesized through multi-component reactions. As the concept of Green Chemistry becomes ever more important, these findings may provide efficient and atom-economical approaches to the diversity-oriented synthesis of bioactive compounds containing a complex structure. This could lead to development of promising drug leads with structural complexity. The work of this thesis will go on to inspire the synthetic research of many readers.
Springer Theses Recognizing Outstanding Ph.D. Research For further volumes: http://www.springer.com/series/8790 Aims and Scope The series ‘‘Springer Theses’’ brings together a selection of the very best Ph.D. theses from around the world and across the physical sciences. Nominated and endorsed by two recognized specialists, each published volume has been selected for its scientific excellence and the high impact of its contents for the pertinent field of research. For greater accessibility to non-specialists, the published versions include an extended introduction, as well as a foreword by the student’s supervisor explaining the special relevance of the work for the field. As a whole, the series will provide a valuable resource both for newcomers to the research fields described, and for other scientists seeking detailed background information on special questions. Finally, it provides an accredited documentation of the valuable contributions made by today’s younger generation of scientists. Theses are accepted into the series by invited nominated only and must fulfill all of the following criteria • They must be written in good English. • The topic of should fall within the confines of Chemistry, Physics and related interdisciplinary fields such as Materials, Nanoscience, Chemical Engineering, Complex Systems and Biophysics. • The work reported in the thesis must represent a significant scientific advance. • If the thesis includes previously published material, permission to reproduce this must be gained from the respective copyright holder. • They must have been examined and passed during the 12 months prior to nomination. • Each thesis should include a foreword by the supervisor outlining the significance of its content. • The theses should have a clearly defined structure including and introduction accessible to scientists not expert in that particular field. Yusuke Ohta Copper-Catalyzed Multi-Component Reactions Synthesis of Nitrogen-Containing Polycyclic Compounds Doctoral Thesis accepted by Kyoto University, Japan 123 Author Dr. Yusuke Ohta Graduate School of Pharmaceutical Sciences, Kyoto University Yoshida-shimo-adachi-cho 46-29 Sakyo-ku, Kyoto 606-8501 Japan e-mail:
[email protected] Supervisors Prof. Yoshiji Takemoto and Prof. Nobutaka Fujii Graduate School of Pharmaceutical Sciences, Kyoto University Yoshida-shimo-adachi-cho 46-29 Sakyo-ku, Kyoto 606-8501 Japan e-mail: ISSN 2190-5053 e-ISSN 2190-5061 ISBN 978-3-642-15472-0 e-ISBN 978-3-642-15473-7 DOI 10.1007/978-3-642-15473-7 Spri