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Synthesis of fused tetrazole derivatives via a tandem cycloaddition and N-allylation reaction and parallel synthesis of fused tetrazole amines

Ek, Fredrik LU orcid ; Manner, Sophie LU ; Wistrand, Lars-Göran and Frejd, Torbjörn LU (2004) In Journal of Organic Chemistry 69(4). p.1346-1352
Abstract
A method for the synthesis of novel fused tricyclic tetrazoles from allylic bromides generated by the recently discovered DiazAll reaction has been developed. This new tandem reaction comprises a cycloaddition between a nitrile and (TMS)N-3 followed by an intramolecular N-allylation. The variation of functionalities in the benzene moiety was well-tolerated, and only a moderate difference in yield and degree of purity was noticed. An exo-methylene group in these new compounds permitted further derivatization. Structural resemblance with substances which possess important pharmacological properties motivated the synthesis of a series of ketones and a small library of amines.
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author
; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Journal of Organic Chemistry
volume
69
issue
4
pages
1346 - 1352
publisher
The American Chemical Society (ACS)
external identifiers
  • pmid:14961689
  • wos:000188955400043
  • scopus:1242307323
  • pmid:14961689
ISSN
1520-6904
DOI
10.1021/jo035498c
language
English
LU publication?
yes
additional info
The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240), Chemical Biology and Drug Discovery (013210700)
id
9673d142-578c-495b-b97d-3b9b7549f15c (old id 139458)
date added to LUP
2016-04-01 12:09:41
date last changed
2025-10-14 11:21:52
@article{9673d142-578c-495b-b97d-3b9b7549f15c,
  abstract     = {{A method for the synthesis of novel fused tricyclic tetrazoles from allylic bromides generated by the recently discovered DiazAll reaction has been developed. This new tandem reaction comprises a cycloaddition between a nitrile and (TMS)N-3 followed by an intramolecular N-allylation. The variation of functionalities in the benzene moiety was well-tolerated, and only a moderate difference in yield and degree of purity was noticed. An exo-methylene group in these new compounds permitted further derivatization. Structural resemblance with substances which possess important pharmacological properties motivated the synthesis of a series of ketones and a small library of amines.}},
  author       = {{Ek, Fredrik and Manner, Sophie and Wistrand, Lars-Göran and Frejd, Torbjörn}},
  issn         = {{1520-6904}},
  language     = {{eng}},
  number       = {{4}},
  pages        = {{1346--1352}},
  publisher    = {{The American Chemical Society (ACS)}},
  series       = {{Journal of Organic Chemistry}},
  title        = {{Synthesis of fused tetrazole derivatives via a tandem cycloaddition and N-allylation reaction and parallel synthesis of fused tetrazole amines}},
  url          = {{http://dx.doi.org/10.1021/jo035498c}},
  doi          = {{10.1021/jo035498c}},
  volume       = {{69}},
  year         = {{2004}},
}