Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact: purchase@heterocycles.com

Price: ¥ 4,320 (Yen only)
Period: This Article can be accessed for 7 days.

Paper | Regular issue | Vol 65, No. 1, 2005, pp.117-131
Published online, 19th November, 2004
DOI: 10.3987/COM-04-10242
Electron Transfer-initiated and Highly Selective Photocyclization of N-Acyl-α-dehydroarylalaninamides to 3,4-Dihydroquinolinone Derivatives

Kei Maekawa, Kunio Fujita, Katsuyuki Iizuka, Tetsutaro Igarashi, and Tadamitsu Sakurai*

*Departmnet of Applied Chemistry, Faculty of Engineering, Kanagawa University, 3-27-1 Rokkakubashi, Kanagawa-ku, Yokohama 221-8686, Japan

Abstract

The irradiation of (Z)-N-acyl-α-dehydroarylalaninamides [(Z)-1] in methanol containing 1,8-diazabicyclo[5.4.0]undec-7-ene gave substituted 3,4-dihydro-2-quinolinones (2) in high yields along with minor amounts of 2-quinolinone (3) and 4,5-dihydrooxazole (4) derivatives. Analysis of substituent and tertiary amine base effects on the selectivity of each product showed that 2 and 4 are formed via electron transfer from the amine to the excited-state (E)-1, the cyclization of which proceeds in competition with this electron transfer to afford 3.