Halogenation of pyrazoloquinolines and pyrazoloisoquinolines. Theoretical analysis of the regioreactivity and cross-coupling of 3-halogen derivativesâ Spectral and theoretical data are available as supplementary data. For direct electronic access see http://www.rsc.org/suppdata/p1/b0/b006435l/
Pawlas, Jan; Greenwood, Jeremy; Vedsø, Per; Liljefors, Tommy; Jakobsen, Palle; Huusfeldt, Per Olaf; Begtrup, Mikael; Pawlas Jan; Department of Medicinal Chemistry, The Royal Danish School of Pharmacy; Greenwood Jeremy; Department of Medicinal Chemistry, The Royal Danish School of Pharmacy; Vedsø Per; Department of Medicinal Chemistry, The Royal Danish School of Pharmacy; Liljefors Tommy; Department of Medicinal Chemistry, The Royal Danish School of Pharmacy; Jakobsen Palle; Medicinal Chemistry Research; Huusfeldt Per Olaf; Medicinal Chemistry Research; Begtrup Mikael; Department of Medicinal Chemistry, The Royal Danish School of Pharmacy
Журнал:
Journal of the Chemical Society, Perkin Transactions 1
Дата:
2001
Аннотация:
Selective C*â C* indicates C-3 for pyrazoles 2 and 4 and C-1 for pyrazoles 1 and 3. halogenation (I and Br) of pyrazoles 1a, 3a and 4a gave halopyrazoles 5, 7â 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.
350.1Кб