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

Fredrik Ek, Lars-Göran Wistrand, Torbjörn Frejd

Forskningsoutput: TidskriftsbidragArtikel i vetenskaplig tidskriftPeer review

Sammanfattning

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.
Originalspråkengelska
Sidor (från-till)1911-1918
TidskriftJournal of Organic Chemistry
Volym68
Nummer5
DOI
StatusPublished - 2003

Bibliografisk information

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)

Ämnesklassifikation (UKÄ)

  • Organisk kemi

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