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
    info

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

Journal:
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

Metrics

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

Abstract

(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.