Preparation of α,β-Unsaturated
Lactams through Intramolecular Electrophilic Carbamoylation
of Alkenes

Yoshizumi Yasui; Issei Kakinokihara; Hiroshi Takeda; Yoshiji Takemoto

doi:10.1055/s-0029-1217028

PAPER

Preparation of α,β-Unsaturated Lactams through Intramolecular Electrophilic Carbamoylation of Alkenes

Yoshizumi Yasui^a, Issei Kakinokihara^b, Hiroshi Takeda^b, Yoshiji Takemoto*^b
^a WPI Advanced Institute for Materials Research, Tohoku University, Aoba, Sendai 980-8577, Japan
^b Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan
Fax: +81(75)7534569; e-Mail: takemoto@pharm.kyoto-u.ac.jp;

Abstract

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Abstract

A general synthetic method for the preparation of α,β-unsaturated lactams starting from alkenylchloroformamides has been developed. The reaction was complete within five minutes at 150 ˚C in N-methylpyrrolidone with a catalytic amount of HBr under microwave irradiation. Not only six-membered lactams, but also five- and seven-membered lactams were obtained in high yields.

Key words

lactam - cyclization - electrophilic addition - acid catalyst - microwave

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Referenzen

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