Issue 8, 2001
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Halogenation of pyrazoloquinolines and pyrazoloisoquinolines. Theoretical analysis of the regioreactivity and cross-coupling of 3-halogen derivatives †

Jan Pawlas,a   Jeremy Greenwood,a   Per Vedsø,a   Tommy Liljefors,a   Palle Jakobsen,b   Per Olaf Huusfeldtb  and  Mikael Begtrup*a  

* Corresponding authors

a Department of Medicinal Chemistry, The Royal Danish School of Pharmacy, Universitetsparken 2, Copenhagen, Denmark
E-mail: begtrup@dfh.dk
Fax: (45) 35306040

b Medicinal Chemistry Research, Novo Nordisk Park, Måløv, Denmark

Abstract

Selective C* halogenation (I and Br) of pyrazoles 1a, 3a and 4a gave halopyrazoles 5, 7–9, 11, 12. Reactivity differences between 1a, 3a and 4a, and the failure of 2a to give the expected halopyrazoles 6, 10 were explained using calculated relative energies of bromination, and inspection of frontier molecular orbitals. Utility of the prepared halides was demonstrated by a series of palladium-catalysed cross-coupling reactions.

Graphical abstract: Halogenation of pyrazoloquinolines and pyrazoloisoquinolines. Theoretical analysis of the regioreactivity and cross-coupling of 3-halogen derivatives [ ]

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Article information

DOI
https://doi.org/10.1039/B006435L
Article type
Paper
Submitted
07 Aug 2000
Accepted
16 Nov 2000
First published
26 Jan 2001

J. Chem. Soc., Perkin Trans. 1, 2001, 861-866

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Halogenation of pyrazoloquinolines and pyrazoloisoquinolines. Theoretical analysis of the regioreactivity and cross-coupling of 3-halogen derivatives

J. Pawlas, J. Greenwood, P. Vedsø, T. Liljefors, P. Jakobsen, P. O. Huusfeldt and M. Begtrup, J. Chem. Soc., Perkin Trans. 1, 2001, 861 DOI: 10.1039/B006435L

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