Beilstein J. Org. Chem.2009,5, No. 66, doi:10.3762/bjoc.5.66
-methyl-3-oxo-pentanoic acid phenylamide with tertiarybutylcarbazate and subsequent condensation of the resulting carbamate derivative with a chalcone provided a facile new approach to pyrrolo[1,2-b]pyridazine derivatives.
Keywords: 1,4-diketone; migration and cyclization; pyrrolo[1,2-b]pyridazine
; tertiary butyl carbamate; tertiarybutylcarbazate; α,β-unsaturated ketone; Introduction
Pyrrolopyridazine derivatives have various biological applications [1][2][3][4][5][6][7][8], and their fluorescent properties have been investigated for potential use in sensors, lasers, and semiconductor devices [9
]pyridazines through a hitherto unprecedented approach from a BOC-protected 1-aminopyrrole derivative and α,β-unsaturated ketones.
Results and Discussion
2-[2-(4-Fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxo-pentanoic acid phenylamide 1 was reacted with tertiarybutylcarbazate 2 in toluene and cyclohexane