SYNTHETIC APPROACHES TO 2-SUBSTITUTED 1-OXOTETRAHYDROISOQUINOLINES AND 3-OXOTETRAHYDROISOQUINOLINES

Authors
CHENG CY TSAI HB LIN MS
Citation
Cy. Cheng et al., SYNTHETIC APPROACHES TO 2-SUBSTITUTED 1-OXOTETRAHYDROISOQUINOLINES AND 3-OXOTETRAHYDROISOQUINOLINES, Journal of heterocyclic chemistry, 32(1), 1995, pp. 73-77
Citations number
12
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of heterocyclic chemistry → ACNP
ISSN journal
0022152X
Volume
32
Issue
1
Year of publication
1995
Pages
73 - 77
Database
ISI
SICI code
0022-152X(1995)32:1<73:SAT21A>2.0.ZU;2-U
Abstract
2-Substituted homophthalimides 2a-c were reduced regioselectively with sodium borohydride to carbinol-lactam intermediates 3a-c, which were dehydrated, followed by hydrogenation, to give 1-oxo-tetrahydroisoquin olines or 3,4-dihydroisoquinolin-1(2H)ones 5a-c. The isomeric 3-oxo-te trahydro-isoquinolines or 1,4-dihydroisoquinolin-3(2H)-ones 8a-i were obtained in satisfactory yields via heating 3-isochromanone (6) with t he corresponding amines 7a-i in the presence of aluminum chloride.