Synthesis of fused tetrazole derivatives via a tandem cycloaddition and N-allylation reaction and parallel synthesis of fused tetrazole amines
(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.
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/139458
- author
- Ek, Fredrik LU ; Manner, Sophie LU ; Wistrand, Lars-Göran and Frejd, Torbjörn LU
- organization
- publishing date
- 2004
- 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
- 2022-02-18 18:44:20
@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}}, }