A Simple Synthesis of 5-(2-Aminophenyl)-1H-pyrazoles
Monika Janjić
Faculty of Chemistry and Chemical Technology, University of Ljubljana, Aškerčeva 5, P.O. Box 537, SI-1000 Ljubljana (phone: +386 1 2419 100; fax: +386 1 2419 220)
Search for more papers by this authorRok Prebil
Faculty of Chemistry and Chemical Technology, University of Ljubljana, Aškerčeva 5, P.O. Box 537, SI-1000 Ljubljana (phone: +386 1 2419 100; fax: +386 1 2419 220)
Search for more papers by this authorUroš Grošelj
Faculty of Chemistry and Chemical Technology, University of Ljubljana, Aškerčeva 5, P.O. Box 537, SI-1000 Ljubljana (phone: +386 1 2419 100; fax: +386 1 2419 220)
Search for more papers by this authorDavid Kralj
Faculty of Chemistry and Chemical Technology, University of Ljubljana, Aškerčeva 5, P.O. Box 537, SI-1000 Ljubljana (phone: +386 1 2419 100; fax: +386 1 2419 220)
Search for more papers by this authorČrt Malavašič
Faculty of Chemistry and Chemical Technology, University of Ljubljana, Aškerčeva 5, P.O. Box 537, SI-1000 Ljubljana (phone: +386 1 2419 100; fax: +386 1 2419 220)
Search for more papers by this authorAmalija Golobič
Faculty of Chemistry and Chemical Technology, University of Ljubljana, Aškerčeva 5, P.O. Box 537, SI-1000 Ljubljana (phone: +386 1 2419 100; fax: +386 1 2419 220)
Search for more papers by this authorKatarina Stare
Faculty of Chemistry and Chemical Technology, University of Ljubljana, Aškerčeva 5, P.O. Box 537, SI-1000 Ljubljana (phone: +386 1 2419 100; fax: +386 1 2419 220)
Search for more papers by this authorGeorg Dahmann
Boehringer Ingelheim Pharma GmbH & Co. KG , Department Chemical Research, D-88397 Biberach
Search for more papers by this authorBranko Stanovnik
Faculty of Chemistry and Chemical Technology, University of Ljubljana, Aškerčeva 5, P.O. Box 537, SI-1000 Ljubljana (phone: +386 1 2419 100; fax: +386 1 2419 220)
Search for more papers by this authorCorresponding Author
Jurij Svete
Faculty of Chemistry and Chemical Technology, University of Ljubljana, Aškerčeva 5, P.O. Box 537, SI-1000 Ljubljana (phone: +386 1 2419 100; fax: +386 1 2419 220)
Faculty of Chemistry and Chemical Technology, University of Ljubljana, Aškerčeva 5, P.O. Box 537, SI-1000 Ljubljana (phone: +386 1 2419 100; fax: +386 1 2419 220)Search for more papers by this authorMonika Janjić
Faculty of Chemistry and Chemical Technology, University of Ljubljana, Aškerčeva 5, P.O. Box 537, SI-1000 Ljubljana (phone: +386 1 2419 100; fax: +386 1 2419 220)
Search for more papers by this authorRok Prebil
Faculty of Chemistry and Chemical Technology, University of Ljubljana, Aškerčeva 5, P.O. Box 537, SI-1000 Ljubljana (phone: +386 1 2419 100; fax: +386 1 2419 220)
Search for more papers by this authorUroš Grošelj
Faculty of Chemistry and Chemical Technology, University of Ljubljana, Aškerčeva 5, P.O. Box 537, SI-1000 Ljubljana (phone: +386 1 2419 100; fax: +386 1 2419 220)
Search for more papers by this authorDavid Kralj
Faculty of Chemistry and Chemical Technology, University of Ljubljana, Aškerčeva 5, P.O. Box 537, SI-1000 Ljubljana (phone: +386 1 2419 100; fax: +386 1 2419 220)
Search for more papers by this authorČrt Malavašič
Faculty of Chemistry and Chemical Technology, University of Ljubljana, Aškerčeva 5, P.O. Box 537, SI-1000 Ljubljana (phone: +386 1 2419 100; fax: +386 1 2419 220)
Search for more papers by this authorAmalija Golobič
Faculty of Chemistry and Chemical Technology, University of Ljubljana, Aškerčeva 5, P.O. Box 537, SI-1000 Ljubljana (phone: +386 1 2419 100; fax: +386 1 2419 220)
Search for more papers by this authorKatarina Stare
Faculty of Chemistry and Chemical Technology, University of Ljubljana, Aškerčeva 5, P.O. Box 537, SI-1000 Ljubljana (phone: +386 1 2419 100; fax: +386 1 2419 220)
Search for more papers by this authorGeorg Dahmann
Boehringer Ingelheim Pharma GmbH & Co. KG , Department Chemical Research, D-88397 Biberach
Search for more papers by this authorBranko Stanovnik
Faculty of Chemistry and Chemical Technology, University of Ljubljana, Aškerčeva 5, P.O. Box 537, SI-1000 Ljubljana (phone: +386 1 2419 100; fax: +386 1 2419 220)
Search for more papers by this authorCorresponding Author
Jurij Svete
Faculty of Chemistry and Chemical Technology, University of Ljubljana, Aškerčeva 5, P.O. Box 537, SI-1000 Ljubljana (phone: +386 1 2419 100; fax: +386 1 2419 220)
Faculty of Chemistry and Chemical Technology, University of Ljubljana, Aškerčeva 5, P.O. Box 537, SI-1000 Ljubljana (phone: +386 1 2419 100; fax: +386 1 2419 220)Search for more papers by this authorAbstract
A four-step synthesis of 1-substituted 5-(2-aminophenyl)-1H-pyrazoles 5 as a novel type of histamine analogs and versatile building blocks for further transformations was developed. The synthesis starts from commercially available 2-nitroacetophenone (12), which is converted into the enamino ketone 13 as the key intermediate. Cyclization of the key intermediate 13 with monosubstituted hydrazines 14a–14l afforded the 5-(2-nitrophenyl)-1H-pyrazoles 17a–17l. Finally, catalytic hydrogenation of the nitro compounds 17a, 17c–17e, and 17g–17j furnished the title compounds 5a, 5c–5e, and 5g–5j, respectively, in good yields. As demonstrated by some further transformations, additional functionalization of compounds 17 and 5 is feasible, either by electrophilic substitution at C(4) of the pyrazole ring, or at the NH2 group.
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