A NEW REGIOSPECIFIC METHOD FOR THE SYNTHESIS OF SUBSTITUTED PHENANTHRIDINES AND BENZO[J]PHENANTHRIDINES VIA AROMATIC ANNELATION OF LTHIO)METHYLENE]-1,2,3,4-TETRAHYDROQUINOLINE-4-ONE

Authors
PATRA PK SURESH JR ILA H JUNJAPPA H
Citation
Pk. Patra et al., A NEW REGIOSPECIFIC METHOD FOR THE SYNTHESIS OF SUBSTITUTED PHENANTHRIDINES AND BENZO[J]PHENANTHRIDINES VIA AROMATIC ANNELATION OF LTHIO)METHYLENE]-1,2,3,4-TETRAHYDROQUINOLINE-4-ONE, Tetrahedron, 54(34), 1998, pp. 10167-10178
Citations number
48
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
34
Year of publication
1998
Pages
10167 - 10178
Database
ISI
SICI code
0040-4020(1998)54:34<10167:ANRMFT>2.0.ZU;2-2
Abstract
A new efficient method for the synthesis of substituted phenanthridine s, benzo[j]phenanthridines and naphtho[2,1-j]phenanthridines is descri bed. The method involves reaction of alpha-oxoketene dithioacetal 2 wi th allyl (3a), methallyl (3b), benzyl (11a-f) and 1-naphthylmethyl (20 ) magnesium halides followed by cyclization of the resulting carbinola cetals in the presence of BF3.Et2O in refluxing benzene. The dihydroph enanthridines thus obtained were aromatized by treatment with a base i n the presence of phase transfer catalyst. (C) 1998 Published by Elsev ier Science Ltd. All rights reserved.