Nagarajan, K. ; Rajagopalan, P. ; Advani, B. G. ; Ranga Rao, V. ; Bhat, G. A. (1992) Synthesis of trans-N-2-aryl(heteryl)ethenamidines Proceedings of the Indian Academy of Sciences - Chemical Sciences, 104 (3). pp. 383-397. ISSN 0253-4134
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Official URL: http://www.ias.ac.in/j_archive/chemsci/104/2/383-3...
Abstract
2-Amino-2-arylethylamides 1 carrying electron-donating substituents in the para position are transformed by hot POC13 to the the title compounds 2, presumably via iminochlorides 7 and imidazolium derivatives 8. Amides lacking this para-substituent give rise to chloroamidines 11 under these conditions.m-Methoxyphenethylamide1t and POCl3 form, besides 11f, an isoquinoline derivative 3. The involvement of an imidazolium compound 8 in the formation of ethenamidines has been verified by the synthesis of 2a from 10. Reaction of amide lw with PCl5 in the cold leads to, besides the chloroamidine11c, the cis-ethenamidine12 which equilibrates with thetrans-isomer 2o in hot toluene. Thienylethyl urea 13 converted by hot POCl3 to the imidazoline16, while phenylpropylamide 17 forms only the iminochloride18a.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Indian Academy of Sciences. |
| Keywords: | Ethenamidine; α-chloroamidine; Anomalous Bischler-Napieralski Reaction; Imidazoline; 2-azabutadienes |
| ID Code: | 90830 |
| Deposited On: | 14 May 2012 13:51 |
| Last Modified: | 14 May 2012 13:51 |
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