A new Claisen sequence for the synthesis of 3-substituted-2-oxindoles

Tetrahedron Letters

Volumn 41, Issue 23, 2000, Pages 4657-4661

  Booker Milburn, Kevin I ^a   Fedouloff, Michael ^b   Paknoham, Sandra J ^b   Strachan, John B ^b   Melville, James L ^b   Voyle, Martyn ^b  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; SYNTHESIS;

EID: 0034640982     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00649-3     Document Type: Article

References (8)

1. (a) Fedouloff, M.; Strachan, J. B. (SmithKline Beecham plc, UK) Patent WO 99-EP4944 19990713.
2. (b) Fedouloff, M.; Strachan, J. B. (SmithKline Beecham plc, UK) Patent WO 99-EP4943 19990713.
3. For specific indole Claisen rearrangements, see: (a) Somei, M.; Yamada, F.; Fukui, Y.; Shinmyo, D. Heterocycles 1993, 35, 99.
4. (b) Somei, M.; Yamada, F.; Izumi, T.; Nakajou, M. Heterocycles 1997, 45, 2327.
5. (c) Sakamoto, M.; Kawasaki, T.; Tarashima, R.; Sakaguchi, K.; Sekiguchi, H. Tetrahedron Lett. 1996, 37, 7525.
6. (d) Merour, J.-Y.; Malapel-Andrieu, B.; Piroelle, S. J. Chem. Res. (S) 1998, 594.
7. 3: C, 67.50%; H, 5.66%; N, 6.06%. Found: C, 67.49%; H, 5.60%; N, 5.99%.
8. For example, cycloadduct 11 exhibited the following NOE enhancements: