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Aromatic Allylation via Diazotization, Variation of the Allylic Moiety and a Short Route to a Benzazepine Derivative.

Ek, Fredrik LU ; Wistrand, Lars-Göran and Frejd, Torbjörn LU (2003) In Journal of Organic Chemistry 68(5). p.1911-1918
Abstract
A continued study of the recently discovered diazotizative allylation (DiazAll) reaction of aniline derivatives is reported. Several allyl reagents, commonly used in radical allylation reactions, were evaluated, and some of these reagents resulted in allylation when used in the DiazAll reaction. The best result was obtained with allyl bromide. Substituted allylic bromides gave the corresponding allyl aromatic compounds in poor to excellent yields. In comparison with an established method for aromatic allylation, the DiazAll reaction performed well and was superior when a more complex allylic bromide was used. Finally, a new allylation-bromocyclization reaction was demonstrated and used in the synthesis of a known inhibitor of... (More)
A continued study of the recently discovered diazotizative allylation (DiazAll) reaction of aniline derivatives is reported. Several allyl reagents, commonly used in radical allylation reactions, were evaluated, and some of these reagents resulted in allylation when used in the DiazAll reaction. The best result was obtained with allyl bromide. Substituted allylic bromides gave the corresponding allyl aromatic compounds in poor to excellent yields. In comparison with an established method for aromatic allylation, the DiazAll reaction performed well and was superior when a more complex allylic bromide was used. Finally, a new allylation-bromocyclization reaction was demonstrated and used in the synthesis of a known inhibitor of phenylethanolamine N-methyltransferase (PNMT), an enzyme involved in the biosynthesis of adrenaline. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Journal of Organic Chemistry
volume
68
issue
5
pages
1911 - 1918
publisher
The American Chemical Society
external identifiers
  • pmid:12608810
  • wos:000181329900036
  • scopus:0242515855
ISSN
1520-6904
DOI
language
English
LU publication?
yes
id
5dcd97a9-eee9-443e-9499-47f6eca5f8d8 (old id 128553)
date added to LUP
2007-07-10 09:36:11
date last changed
2018-05-29 11:57:05
@article{5dcd97a9-eee9-443e-9499-47f6eca5f8d8,
  abstract     = {A continued study of the recently discovered diazotizative allylation (DiazAll) reaction of aniline derivatives is reported. Several allyl reagents, commonly used in radical allylation reactions, were evaluated, and some of these reagents resulted in allylation when used in the DiazAll reaction. The best result was obtained with allyl bromide. Substituted allylic bromides gave the corresponding allyl aromatic compounds in poor to excellent yields. In comparison with an established method for aromatic allylation, the DiazAll reaction performed well and was superior when a more complex allylic bromide was used. Finally, a new allylation-bromocyclization reaction was demonstrated and used in the synthesis of a known inhibitor of phenylethanolamine N-methyltransferase (PNMT), an enzyme involved in the biosynthesis of adrenaline.},
  author       = {Ek, Fredrik and Wistrand, Lars-Göran and Frejd, Torbjörn},
  issn         = {1520-6904},
  language     = {eng},
  number       = {5},
  pages        = {1911--1918},
  publisher    = {The American Chemical Society},
  series       = {Journal of Organic Chemistry},
  title        = {Aromatic Allylation via Diazotization, Variation of the Allylic Moiety and a Short Route to a Benzazepine Derivative.},
  url          = {http://dx.doi.org/},
  volume       = {68},
  year         = {2003},
}