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

Ek, FredrikLund University,Lunds universitet,Kemisk biologi med inriktning mot läkemedelsutveckling,Forskargrupper vid Lunds universitet,Chemical Biology and Therapeutics,Lund University Research Groups (author)

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.

Wistrand, Lars-Göran (author)
Frejd, TorbjörnLund University,Lunds universitet,Centrum för analys och syntes,Kemiska institutionen,Institutioner vid LTH,Lunds Tekniska Högskola,Centre for Analysis and Synthesis,Department of Chemistry,Departments at LTH,Faculty of Engineering, LTH(Swepub:lu)orgk1-tf (author)
Kemisk biologi med inriktning mot läkemedelsutvecklingForskargrupper vid Lunds universitet (creator_code:org_t)

In:Journal of Organic Chemistry: American Chemical Society (ACS)68:5, s. 1911-19181520-69040022-3263

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NATURAL SCIENCES: NATURAL SCIENCES; and Chemical Science ...; and Organic Chemistr ...

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