Synthesis of a C11 spiropiperidino derivative of 8-chloro-6,11- dihydro 5H-benzo[5,6]cyclohepta[1,2-b]pyridine
Publication
, Journal Article
Afonso, A; Kelly, J; Puar, MS; McCombie, S; McPhail, AT
Published in: Tetrahedron Letters
October 15, 1998
A method using N-tosyl aziridine for the synthesis of a spiropiperidine 2 (R=H) is described. Cleavage of the N-tosyl group of the intermediate 8 to form the spiropiperidinone 9 was found to proceed in high yield with conc. sulfuric acid. Acylated derivatives of 2 were required for a structure- activity study aimed at defining the spatial requirements of the N-acyl residue in the lead Farnesyl-Protein-Transferase inhibitor 1.
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Published In
Tetrahedron Letters
DOI
ISSN
0040-4039
Publication Date
October 15, 1998
Volume
39
Issue
42
Start / End Page
7661 / 7664
Related Subject Headings
- Organic Chemistry
- 3405 Organic chemistry
- 3404 Medicinal and biomolecular chemistry
- 3101 Biochemistry and cell biology
- 0305 Organic Chemistry
- 0304 Medicinal and Biomolecular Chemistry
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Afonso, A., Kelly, J., Puar, M. S., McCombie, S., & McPhail, A. T. (1998). Synthesis of a C11 spiropiperidino derivative of 8-chloro-6,11- dihydro 5H-benzo[5,6]cyclohepta[1,2-b]pyridine. Tetrahedron Letters, 39(42), 7661–7664. https://doi.org/10.1016/S0040-4039(98)01714-6
Afonso, A., J. Kelly, M. S. Puar, S. McCombie, and A. T. McPhail. “Synthesis of a C11 spiropiperidino derivative of 8-chloro-6,11- dihydro 5H-benzo[5,6]cyclohepta[1,2-b]pyridine.” Tetrahedron Letters 39, no. 42 (October 15, 1998): 7661–64. https://doi.org/10.1016/S0040-4039(98)01714-6.
Afonso A, Kelly J, Puar MS, McCombie S, McPhail AT. Synthesis of a C11 spiropiperidino derivative of 8-chloro-6,11- dihydro 5H-benzo[5,6]cyclohepta[1,2-b]pyridine. Tetrahedron Letters. 1998 Oct 15;39(42):7661–4.
Afonso, A., et al. “Synthesis of a C11 spiropiperidino derivative of 8-chloro-6,11- dihydro 5H-benzo[5,6]cyclohepta[1,2-b]pyridine.” Tetrahedron Letters, vol. 39, no. 42, Oct. 1998, pp. 7661–64. Scopus, doi:10.1016/S0040-4039(98)01714-6.
Afonso A, Kelly J, Puar MS, McCombie S, McPhail AT. Synthesis of a C11 spiropiperidino derivative of 8-chloro-6,11- dihydro 5H-benzo[5,6]cyclohepta[1,2-b]pyridine. Tetrahedron Letters. 1998 Oct 15;39(42):7661–7664.
Published In
Tetrahedron Letters
DOI
ISSN
0040-4039
Publication Date
October 15, 1998
Volume
39
Issue
42
Start / End Page
7661 / 7664
Related Subject Headings
- Organic Chemistry
- 3405 Organic chemistry
- 3404 Medicinal and biomolecular chemistry
- 3101 Biochemistry and cell biology
- 0305 Organic Chemistry
- 0304 Medicinal and Biomolecular Chemistry