Patra, Pranab K. ; Suresh, J. R. ; Ila, H. ; Junjappa, Hiriyakkanavar (1998) A new regiospecific method for the synthesis of substituted phenanthridines and benzo[j]phenanthridines via aromatic annelation of 1-N-benzenesulfonyl-3-[bis(methylthio)methylene]-1,2,3,4-tetrahydroquinoline-4-one Tetrahedron, 54 (34). pp. 10167-10178. ISSN 0040-4020
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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...
Related URL: http://dx.doi.org/10.1016/S0040-4020(98)00609-7
Abstract
A new efficient method for the synthesis of substituted phenanthridines, benzo[j]phenanthridines and naphtho[2,1-j]phenanthridines is described. The method involves reaction of α-oxoketene dithioacetal 2 with allyl (3a), methallyl (3b), benzyl (11a-f) and 1-naphthylmethyl (20) magnesium halides followed by cyclization of the resulting carbinolacetals in the presence of BF3.Et2O in refluxing benzene. The dihydrophenanthridines thus obtained were aromatized by treatment with a base in the presence of phase transfer catalyst.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| ID Code: | 15273 |
| Deposited On: | 13 Nov 2010 13:01 |
| Last Modified: | 11 Jul 2012 04:31 |
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