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Synthesis oftrans-N-2-aryl(heteryl)ethenamidines

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Abstract

2-Amino-2-arylethylamides1 carrying electron-donating substituents in thepara position are transformed by hot POC13 to the the title compounds2, presumably via iminochlorides 7 and imidazolium derivatives8. Amides lacking this para-substituent give rise to chloroamidines11 under these conditions.m-Methoxyphenethylamide1t and POCl3 form, besides11f, an isoquinoline derivative3. The involvement of an imidazolium compound8 in the formation of ethenamidines has been verified by the synthesis of2a from10. Reaction of amide1w with PCl5 in the cold leads to, besides the chloroamidine11c, thecis-ethenamidine12 which equilibrates with thetrans-isomer2o in hot toluene. Thienylethyl urea13 converted by hot POCl3 to the imidazoline16, while phenylpropylamide17 forms only the iminochloride18a.

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References

  • Advani B G, Nagarajan K, Rajagopalan P and Ranga Rao V 1968Tetrahedron Lett. 56 5825

    Article  Google Scholar 

  • Biere H 1983Eur. Patent ammeldung EP 110 090A

  • Compagnon P L, Gasquez F, Compagnon O and Kimny T 1982Bull. Soc. Chim. Belg. 91 931

    Article  CAS  Google Scholar 

  • Cook S L, Venayak N D and Wakefield B J 1983J. Chem. Res. Synp. 199

  • Cook S L and Wakefield B J 1980J. Chem. Soc., Perkin Trans. I. 2392

  • Ichimura H and Ohta M 1966Tetrahedron Lett. 54 807

    Google Scholar 

  • Islam A M, El-Sharief A M S, Ismail I M and Harb A A 1983Egypt J. Chem. 26 221; 1984Chem. Abstr. 101 191751g

    CAS  Google Scholar 

  • Ito M M, Nomura Y, Takeuchi Y and Tomoda S 1983Bull. Chem. Soc. Jpn. 56 641

    Article  CAS  Google Scholar 

  • Kantlehner W 1979Advances in organic chemistry methods and results (series ed.) E C Taylor. Vol. 9, Part 2.Iminium salts in organic chemistry (eds) H Bohme and H G Viehe (New York: John Wiley & Sons) p.99

  • Marxer A 1972Helv. Chim. Acta 55 430

    Article  CAS  Google Scholar 

  • Matier W L and Corner W T 1974J. Org. Chem. 39 3080

    Article  CAS  Google Scholar 

  • Matier W L and Corner W T 1975Ger. Offen DE 2428223; 1975Chem. Abstr. 82 170425c

    Google Scholar 

  • Matier W L and Corner W T 1977Ger. Offen. DE 2635121; 1977Chem. Abstr. 87 22805q

  • McKillop A and Boulton A J (eds) 1984Comprehensive heterocyclic chemistry (Oxford: Pergamon) vol. 2, p. 442

    Google Scholar 

  • Nagarajan K, Vunnam V R, Shah R K, Shenoy S J, Fritz H, Richter W J and Muller D 1988Helv. Chim. Acta 71 77

    Article  CAS  Google Scholar 

  • Rajagopalan P and Advani B G 1965Tetrahedron Lett. 26 2197

    Article  Google Scholar 

  • Ried W and Erie H E 1979Chem. Ber. 112 640

    Article  CAS  Google Scholar 

  • Va Meeteren H W and Van der Plas H C 1971Recl. Trav. Chim. Pays-Bas 90 105

    Google Scholar 

  • Yanagida S 1975Jpn. Patent 50/37671; 1976Chem. Abstr. 85 108660j

    Google Scholar 

  • Yanagida S, Fujita T, Ohoka M, Katagiri I and Komori S 1973Bull. Chem. Soc. Jpn. 46 292

    Article  CAS  Google Scholar 

Download references

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Author notes

  1. K. Nagarajan

    Present address: Bangalore Pharmaceuticals and Research Laboratories Pvt. Ltd., 45th Cross, 9th Block, Jayanagar, 560 069, Bangalore, India

  2. P. Rajagopalan

    Present address: Medicinal Chemistry Division, Central Research & Development Department, E.I. DuPont de Nemours and Company, Experimental Station, Wilmington, USA

Authors and Affiliations

  1. Hindustan CIBA-GEIGY Ltd., Research Centre, 400063, Bombay, India

    K. Nagarajan, P. Rajagopalan, B. G. Advani, V. Ranga Rao & G. A. Bhat

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  1. K. Nagarajan
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  2. P. Rajagopalan
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  3. B. G. Advani
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  4. V. Ranga Rao
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  5. G. A. Bhat
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Contribution No. 752 from Research Centre

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Nagarajan, K., Rajagopalan, P., Advani, B.G. et al. Synthesis oftrans-N-2-aryl(heteryl)ethenamidines. Proc. Indian Acad. Sci. (Chem. Sci.) 104, 383–397 (1992). https://doi.org/10.1007/BF02839548

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  • DOI: https://doi.org/10.1007/BF02839548

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