EXPERIMENTAL
1H NMR spectra for the synthesized compounds were recorded on a Bruker WM-360 (360 MHz)
spectrometer using DMSO-d6 solvent and TMS internal standard. Monitoring of the course of the amidation of
ester 1 was carried out by TLC on Silufol UV-254 plates in the system hexane-ether (1:2) and revealed using
iodine vapor. Ethyl 1-hydroxy-3-oxo-5,6-dihydro-3H-pyrrolo[3,2,1-ij]quinoline-2-carboxylate 1 was prepared
by the method in [13].
1-Hydroxy-3-oxo-5,6-dihydro-3H-pyrrolo[3,2,1-ij]quinoline-2-carboxylic Acid Methylamide (2a).
A solution of the ethyl ester 1 (2.59 g, 0.01 mol) in ethanol (20 ml) was saturated with gaseous methylamine and
left at room temperature for 3 h. The reaction mixture was diluted with cold water and acidified with dilute
(1 : 1) HCl to pH 4.5-5.0. The precipitated amide 2a was filtered off, washed with water, and dried.
Ethylamide 2b was synthesized by a similar method.
1-Hydroxy-3-oxo-5,6-dihydro-3H-pyrrolo[3,2,1-ij]quinoline-2-carboxylic Acid Allylamide (2c).
Allylamine (0.83 ml, 0.011 mol) was added to a solution of ethyl ester 1 (2.59 g, 0.01 mol) in ethanol (15 ml)
and refluxed using a reflux condenser for 2 h (in the case of other sterically hindered amines the reaction time
was increased to 3-4 h). Work up of the reaction mixture and separation of the final material was carried out as
reported in the previous method.
Alkylamides 2d-q were prepared similarly.
X-ray Structural Investigation. Crystals of the sec-butylamide 2h are triclinic (ethanol). At 20ºC:
a = 7.198(1), b = 8.658(1), c = 12.591(1) Å, α = 71.88(1), β = 82.293(1), γ = 77.59(1)º, V = 726.4(1) Å3,
M = 286.32, Z = 2, space group P , dcalc = 1.309 g/cm3, µ(MoKα) = 0.091 mm-1, F(000) = 304. The parameters
1
r
of the unit cell and intensities of 6179 reflections (2518 independent , Rint = 0.022) were measured on an
Xcalibur-3 diffractometer (MoKα radiation, CCD detector, graphite monochromator, ω-scanning, 2θmax = 50º).
The structure was solved by a direct method using the SHELXTL program package [14]. For refinement
of the structure limits were set on the bond lengths in the randomized fragment of N–Csp3 1.47(1) and Csp3–Csp3
1.54(1) Å. The position of the hydrogen atoms were revealed from electron density difference synthesis and for
the randomized part of the molecule calculated geometrically and refined using the riding model with Uiso = nUeq
for a non-hydrogen atom bound to the given hydrogen (n = 1.5 for a methyl group and n = 1.2 for the remaining
hydrogen atoms). The structures were refined by F2 full matrix least squares analysis in the anisotropic
approximation for non-hydrogen atoms to wR2 = 0.0124 for 2418 reflections (R1 = 0.048 for 1315 reflections
with F>4σ(F), S = 0.869). The full crystallographic information has been placed in the Cambridge structural data
bank (reference CCDC 604003). Interatomic distances and valence angles are given in Tables 3 and 4.
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