Synthesis of Azabicyclo[2.2.n]alkane Systems as Analogues of 3-[1-Methyl-2-(S)-pyrrolidinylmethoxy]pyridine (A-84543)

  1. Carreras, J. 1
  2. Avenoza, A. 1
  3. Busto, J.H. 1
  4. Peregrina, J.M. 1
  1. 1 Universidad de La Rioja

    Universidad de La Rioja

    Logroño, España


Journal of Organic Chemistry

ISSN: 0022-3263

Year of publication: 2007

Volume: 72

Issue: 8

Pages: 3112-3115

Type: Article

DOI: 10.1021/JO0700732 PMID: 17371077 SCOPUS: 2-s2.0-34247246344 WoS: WOS:000245510600051 GOOGLE SCHOLAR

More publications in: Journal of Organic Chemistry


Cited by

  • Scopus Cited by: 12 (12-01-2023)
  • Web of Science Cited by: 12 (31-12-2022)

JCR (Journal Impact Factor)

  • Year 2007
  • Journal Impact Factor: 3.959
  • Journal Impact Factor without self cites: 3.451
  • Article influence score: 1.115
  • Best Quartile: Q1
  • Area: CHEMISTRY, ORGANIC Quartile: Q1 Rank in area: 9/56 (Ranking edition: SCIE)

SCImago Journal Rank

  • Year 2007
  • SJR Journal Impact: 2.389
  • Best Quartile: Q1
  • Area: Organic Chemistry Quartile: Q1 Rank in area: 11/159


(Chemical Equation Presented) This work is connected with the epibatidine field and describes the synthesis of several analogues of compounds that present affinity for nicotinic acetylcholine receptors, such as 3-[1-methyl-2-(S)- pyrrolidinylmethoxy]pyridine (A-84543). These analogues bear a 3-pyridyl ether substituent at the bridgehead carbon of the azabicyclo[2.2.n]alkane system. Particularly, in the case of the 1-substituted 2-azabicyclo-[2.2.2]octane system, a new synthetic route has been developed, which involves the synthesis of a novel rigid sulfamidate that allows the straightforward introduction of nucleophiles. © 2007 American Chemical Society.