Nagarajan, K. ; Talwalker, P. K. ; Shah, R. K. ; Shenoy, S. J. (1985) Antiimplantation agents: Part IV. 4-Benzhydrylidenepiperidines & tetrahydropyran analogues of F 6066 Indian Journal of Chemistry - Section B: Organic and Medicinal Chemistry, 24 . pp. 112-118. ISSN 0376-4699
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Abstract
Several α-(4-pyridyl)benzhydrols (8) have been synthesised by Grignard reaction on 4-aroylpyridines (6) or ethyl isonicotinate (7). The quaternary salts,9 of 8 are reduced catalytically to α-(4-piperidyi)benzhydrols (10) which undergo dehydration to benzhydrylidenepiperidines (11). Demethylation of 11c with HBr affords 11d which is further acelylated to provide 11e, an azaisoster of F 6066. Reduction of 9 with sodium borohydride furnishes the tetrahydropyridyl derivatives (12) which undergo acid-catalysed rearrangement to the benzhydrylidenepiperidin-3-ols 13 (14). Treatment of ethyl tetrahydropyran-4-earboxylate with p-anisylmagnesium bromide affords the benzhydrol (19), which is dehydrated to 20. Among the compounds tested, 8b-8d show moderate antiimplantation activity in rats.
Item Type: | Article |
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Source: | Copyright of this article belongs to National Institute of Science Communication and Information Resources. |
ID Code: | 93495 |
Deposited On: | 19 Jun 2012 08:01 |
Last Modified: | 19 May 2016 06:34 |
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