Novel synthesis of heterocyclic aryl amidines

Tetrahedron Letters

Volumn 39, Issue 33, 1998, Pages 5947-5950

  Tommasi, Ruben A ^a   Macchia, William M ^a   Parker, David T ^a  

^a NOVARTIS PHARMA AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDINE; AMMONIA; CARBON DISULFIDE; HETEROCYCLIC COMPOUND; METHYL IODIDE;

ARTICLE; CRYSTALLIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0032514578     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01222-2     Document Type: Article

References (16)

1. 1. Pinner, A. Die Iminoäther und ihre Derivate, Verlag R. Oppenheim, Berlin, 1892.
2. 2. For copper (I) mediated reactions see: Rousselet, G.; Capdevielle, P.; Maumy, M. Tetrahedron Lett. 1993, 34(40), 6395-6398.
3. 3. For the use of lanthanides in the preparation of amidines see: Forsberg, J., et. al. J. Org. Chem. 1987, 52, 1017-1021.
4. 4. Garigipati, R.S. Tetrahedron Lett. 1990, 14, 1969-1972.
5. 5. Levin, J.; Turos, E.; Weinreb, S. Syn. Comm. 1982, 12, 989-93.
6. 6. Whitten, J.P.; McCarthy, J.R. and Matthews, D.P. Synthesis 1988, pg 470. In our hands, the procedure reported in this paper only led to the 2-bromo analog. Addition of AgOTf to the mixture of CNBr and DMAP effectively removed the bromide from the reaction medium by precipitation and resulted in the production of the desired 2-cyano imidazole as the exclusive product.
7. 7. Holan, G.; Samuel, E. J. Chem. Soc. (C), 1967, 25-29. Ennis, B.C.; Holan, G.; Samuel, E. J. Chem. Soc. (C) 1967, 30-33.
8. 7. Holan, G.; Samuel, E. J. Chem. Soc. (C), 1967, 25-29. Ennis, B.C.; Holan, G.; Samuel, E. J. Chem. Soc. (C) 1967, 30-33.
9. 8. Galeazzi, E.; Guzmán, A.; Nava, J.L. J. Org. Chem. 1995, 60, 1090-1092.
10. 9. It is likely that base would catalyze the loss of a chloride from the 2-substituent, thus generating an exocyclic methylene derivative that would be highly reactive. This analysis is precendented by the work of Holan, et. al. as cited in reference 3.
11. 10. Verkruijsse, H.D.; Brandsma, L. J. Organomet. Chem. 1987, 332, 95-98.
12. 11 Poss, M.; Iwanowicz, E.; Reid, J.; Lin, J.; Gu, Z. Tetrahedron Lett. 1992, 33(40), 5933-5936.
13. 12. Bernthsen and Demselber Annalen 1877, 184, 321. Bristow, N.W., Charlton, P.T., Peak, D.A., Short, W.F. J. Chem. Soc. 1954, 616, 623.
14. 12. Bernthsen and Demselber Annalen 1877, 184, 321. Bristow, N.W., Charlton, P.T., Peak, D.A., Short, W.F. J. Chem. Soc. 1954, 616, 623.
15. 3H (leq.) in isopropanol (10 ml/gram) was added. The ppt of the products was collected by vacuum filtration and dried in vacuo.
16. 3H salts. Yields reported are for the purified salts of the products.