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Synthesis of a C11 spirocyclopropyl derivative of 8-chloro-6,11- dihydro-5h-benzo[5,6]cyclohepta[1,2b]pyridine

Publication ,  Journal Article
Afonso, A; Puar, MS; Kelly, J; McPhail, AT
Published in: Tetrahedron Letters
October 15, 1998
Published version (DOI)

The carbanion derived from 8,11-dichloro-6,11-dihydro-5H- benzo[5,6]cyclohepta[1,2-b] pyridine (3) reacts with methyl acrylate to form the C11 spirocyclopropane carboxylic acid methyl ester 6. Compound 6 was converted in five steps to the N-methyl 2'-ethylamino spirocyclopropane 2 (R=H) which was required for a structure-activity study based on the lead Farnesyl Protein Transferase inhibitor 1.

Duke Scholars

Andrew T. McPhail
Author Andrew T. McPhail Chemistry

Published In

Tetrahedron Letters

DOI

10.1016/S0040-4039(98)01713-4

ISSN

0040-4039

Publication Date

October 15, 1998

Volume

39

Issue

42

Start / End Page

7657 / 7660

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
 

Citation

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ICMJE
MLA
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Afonso, A., Puar, M. S., Kelly, J., & McPhail, A. T. (1998). Synthesis of a C11 spirocyclopropyl derivative of 8-chloro-6,11- dihydro-5h-benzo[5,6]cyclohepta[1,2b]pyridine. Tetrahedron Letters, 39(42), 7657–7660. https://doi.org/10.1016/S0040-4039(98)01713-4
Afonso, A., M. S. Puar, J. Kelly, and A. T. McPhail. “Synthesis of a C11 spirocyclopropyl derivative of 8-chloro-6,11- dihydro-5h-benzo[5,6]cyclohepta[1,2b]pyridine.” Tetrahedron Letters 39, no. 42 (October 15, 1998): 7657–60. https://doi.org/10.1016/S0040-4039(98)01713-4.
Afonso A, Puar MS, Kelly J, McPhail AT. Synthesis of a C11 spirocyclopropyl derivative of 8-chloro-6,11- dihydro-5h-benzo[5,6]cyclohepta[1,2b]pyridine. Tetrahedron Letters. 1998 Oct 15;39(42):7657–60.
Afonso, A., et al. “Synthesis of a C11 spirocyclopropyl derivative of 8-chloro-6,11- dihydro-5h-benzo[5,6]cyclohepta[1,2b]pyridine.” Tetrahedron Letters, vol. 39, no. 42, Oct. 1998, pp. 7657–60. Scopus, doi:10.1016/S0040-4039(98)01713-4.
Afonso A, Puar MS, Kelly J, McPhail AT. Synthesis of a C11 spirocyclopropyl derivative of 8-chloro-6,11- dihydro-5h-benzo[5,6]cyclohepta[1,2b]pyridine. Tetrahedron Letters. 1998 Oct 15;39(42):7657–7660.
Journal cover image

Published In

Tetrahedron Letters

DOI

10.1016/S0040-4039(98)01713-4

ISSN

0040-4039

Publication Date

October 15, 1998

Volume

39

Issue

42

Start / End Page

7657 / 7660

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