SIMULTANEOUS FORMATION OF ISOQUINOLINE AND 1-AZETINE DERIVATIVES VIA PHOTOACETYL MIGRATION OF SUBSTITUTED ALPHA-DEHYDROPHENYLALANINE

Authors
KUBO K YAEGASHI S SASAKI K SAKURAI T INOUE H
Citation
K. Kubo et al., SIMULTANEOUS FORMATION OF ISOQUINOLINE AND 1-AZETINE DERIVATIVES VIA PHOTOACETYL MIGRATION OF SUBSTITUTED ALPHA-DEHYDROPHENYLALANINE, Tetrahedron letters, 37(33), 1996, pp. 5917-5920
Citations number
29
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
33
Year of publication
1996
Pages
5917 - 5920
Database
ISI
SICI code
0040-4039(1996)37:33<5917:SFOIA1>2.0.ZU;2-7
Abstract
Irradiation of substituted alpha-dehydrophenylalanine in methanol or a cetonitrile with Pyrex-filtered light was found to give isoquinoline a nd 1-azetine derivatives in relatively good yields, which may be forme d via 1,5-acetyl shift from the (Z)-isomer and 1,3-acetyl migration fr om the (E)-isomer, respectively. The photoreaction in methanol afforde d the azetine in preference to the isoquinoline, while the reverse res ult was obtained in acetonitrile. Copyright (C) 1996 Elsevier Science Ltd