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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 ; 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
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
external identifiers
  • pmid:14961689
  • wos:000188955400043
  • scopus:1242307323
ISSN
1520-6904
DOI
10.1021/jo035498c
language
English
LU publication?
yes
id
9673d142-578c-495b-b97d-3b9b7549f15c (old id 139458)
date added to LUP
2007-07-10 09:33:44
date last changed
2017-04-30 08:36:18
@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},
  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},
  volume       = {69},
  year         = {2004},
}