The Use of an Unusual Rearrangement Sequence for the Syntheses of 3-(1-Aminoalkylidene)-3H-thiophen-2-ones and two Examples of their Surprising Electrophilic-Induced Dimerization Reactions

Advanced Synthesis and Catalysis

Volumn 342, Issue 1, 2000, Pages 75-79

  Walter, Harald ^a   Rothen, Hans Peter ^a   Winkler, Tammo ^a  

^a NOVARTIS PHARMA AG   (Switzerland)

Author keywords

Cyclizations; Grignard reactions; Rearrangements; Sulfur heterocycles; Thiophenone

Indexed keywords

EID: 0347616749     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3897(200001)342:1<75::aid-prac75>3.0.co;2-w     Document Type: Article

References (8)

1. S. Gronowitz, J. Fortea-Laguna, S. Ross, B. Sjoberg, W. E. Stjernstrom, Acta Pharm. Suecica, 1968, 5, 563
2. P. E. Hansen, Prog. NMR Spectroscopy 1981, 14, 175
3. A. Bax, M. E Summers, J. Am. Chem. Soc. 1986, 106, 2093
4. S. Gronowitz, I. Johnson, A. B. Hörnfeldt, Chem. Scripta 1975, 7, 76
5. A. F. M. Fahmy, A. F. Shaaban, M. M. H. Arief, M. S. Amine, Egypt. J. Chem. 1989, 32, 581
6. The presented mechanism, in some points, is similar to the one used by R. Heckendorn et al. (R.Heckendorn, A.R. Gagneux, Tetrahedron Lett. 1973, 25, 2279) for explaining the reaction of 2-amino-3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophene with phenylmagnesium bromide.
7. 13C-NMR-Spektroskopie, Georg Thieme Verlag, Stuttgart 1984, p. 449
8. H. Walter, unpublished results