Synthesis 2020; 52(07): 1113-1121
DOI: 10.1055/s-0039-1691575
paper
© Georg Thieme Verlag Stuttgart · New York

Transition-Metal-Free Synthesis of Pyridine Derivatives by Thermal Cyclization of N-Propargyl Enamines

Yuya Chikayuki
,
Takakane Miyashige
,
Shiori Yonekawa
,
Akiko Kirita
,
Natsuko Matsuo
,
Hiroyoshi Teramoto
,
Shigeru Sasaki
,
Kimio Higashiyama
,
Takayasu Yamauchi
Institute of Medicinal Chemistry, Hoshi University, Ebara, Shinagawa, Tokyo 142-8501, Japan   Email: yamauchi@hoshi.ac.jp
› Author Affiliations
Further Information

Publication History

Received: 16 November 2019

Accepted after revision: 27 December 2019

Publication Date:
21 January 2020 (online)


Abstract

A transition-metal-free synthesis of pyridine derivatives by 6-endo-dig cyclization of N-propargyl enamines was developed. This method is environmentally friendly and is a high atom economy reaction that is easily accessed to provide pyridine derivatives in moderate to good yield by heating N-propargyl enamines in solvent without additives. The total synthesis of onychine was achieved in 51% yield in only two steps by using this method.

Supporting Information