2394
VYDZHAK, PANCHISHIN
Table 2. (Contd.)
Comp.
no.
IR spectrum (KBr),a ν, cm–1
1H NMR spectrum, δ, ppm
1608 (C=C); 1652 (C9=O); 2.90 m (1H, HB NCH2), 3.24 s (3H, OCH3), 3.45 m (2H, OCH2), 3.86 m (1H, HA NCH2), 5.74 s
XIc
1710 (C3=O)
(1H, 1-H), 7.11–7.18 m (2H, Harom), 7.36–7.41 m (2H, Harom) 7.53 m (1H, 7-H), 7.69–7.90 m (2H,
5-H, 6-H), 8.02 d.d (1H, 8-H)
1607 (C=C); 1652 (C9=O); 2.87 m (1H, HB NCH2), 3.24 s (3H, OCH3), 3.44 m (2H, OCH2), 3.76 s (3H, OCH3), 3.86 m (1H,
XIf
1710 (C3=O)
HA NCH2), 5.65 s (1H, 1-H), 6.89 d (2H, Harom), 7.21 d (2H, Harom) 7.52 m (1H, 7-H), 7.69–7.90 m
(2H, 5-H, 6-H), 8.02 d.d (1H, 8-H)
2
1609 (C=C); 1657 (C9=O); 3.84 d (1H, 2JHH 15.3 Hz, HB NCH2), 4.97 d (1H, JHH 15.3 Hz, HA NCH2), 5.39 s (1H, 1-H), 7.13–
XIIa
XIIb
1713 (C3=O)
1608 (C=C); 1653 (C9=O); 2.33 s (3H, CH3), 3.79 d (1H, 2JHH 15.3 Hz, HB NCH2), 4.97 d (1H, 2JHH 15.3 Hz, HA NCH2), 5.33 s
7.39 m (10H, Harom) 7.51 m (1H, 7-H), 7.79–7.90 m (2H, 5-H, 6-H), 8.01 d.d (1H, 8-H)
1714 (C3=O)
(1H, 1-H), 7.11–7.35 m (9H, Harom), 7.52 m (1H, 7-H), 7.80–7.90 m (2H, 5-H, 6-H), 8.01 d.d (1H,
8-H)
1608 (C=C); 1654 (C9=O); 3.79 d (1H, 2JHH 15.3 Hz, HB NCH2), 4.97 d (1H, 2JHH 15.3 Hz, HA NCH2), 5.33 s (1H, 1-H), 7.08–
1714 (C3=O)
7.36 m (9H, Harom), 7.52 m (1H, 7-H), 7.80–7.90 m (2H, 5-H, 6-H), 8.01 d.d (1H, 8-H)
1609 (C=C); 1658 (C9=O); 3.92 d (1H, 2JHH 15.3 Hz, HB NCH2), 4.94 d (1H, 2JHH 15.3 Hz, HA NCH2), 5.44 s (1H, 1-H), 7.13–
1715 (C3=O)
7.39 m (9H, Harom), 7.52 m (1H, 7-H), 7.80–7.90 m (2H, 5-H, 6-H), 8.01 d.d (1H, 8-H)
1611 (C=C); 1653 (C9=O); 2.69 m (1H, HB NCH2), 2.84–3.02 m (2H, CH2Ph), 3.90 m (1H, HA NCH2), 5.54 s (1H, 1-H), 7.10–
1708 (C3=O)
7.40 m (10H, Harom), 7.52 m (1H, 7-H), 7.69–7.90 m (2H, 5-H, 6-H), 8.02 d.d (1H, 8-H)
1609 (C=C); 1659 (C9=O); 2.75 m (1H, HB NCH2), 2.86–3.02 m (2H, CH2Ph), 3.94 m (1H, HA NCH2), 5.59 s (1H, 1-H), 7.12–
1710 (C3=O)
7.42 m (9H, Harom), 7.52 m (1H, 7-H), 7.69–7.90 m (2H, 5-H, 6-H), 8.02 d.d (1H, 8-H)
1611 (C=C); 1650 (C9=O); 2.74 m (1H, HB NCH2), 2.86–3.03 m (2H, CH2Ph), 3.75 s (3H, OCH3), 3.88 m (1H, HA NCH2), 5.47
XIIc
XIId
XIIIa
XIIId
XIIIf
1712 (C3=O)
s (1H, 1-H), 6.87 d (2H, Harom), 7.13–7.29 m (7H, Harom), 7.51 m (1H, 7-H), 7.69–7.90 m (2H, 5-H,
6-H), 8.01 d.d (1H, 8-H)
1608 (C=C); 1654 (C9=O); 3.88 d (1H, 2JHH 15.9 Hz, HB NCH2), 4.95 d (1H, 2JHH 15.9 Hz, HA NCH2), 5.46 s (1H, 1-H), 6.22 m
XIVa
XIVb
1709 (C3=O)
(1H, furyl), 6.34 m (1H, furyl), 7.28–7.40 m (5H, Harom), 7.49–7.58 m (2H, 7-H, 1H, furyl), 7.79–
7.90 m (2H, 5-H, 6-H), 8.01 d.d (1H, 8-H)
1608 (C=C); 1652 (C9=O); 2.33 s (3H, CH3), 3.83 d (1H, 2JHH 15.9 Hz, HB NCH2), 4.95 d (1H, 2JHH 15.9 Hz, HA NCH2), 5.40 s
1716 (C3=O)
(1H, 1-H), 6.23 m (1H, furyl), 6.35 m (1H, furyl), 7.15–7.20 m (4H, Harom), 7.48–7.56 m (2H, 7-H,
1H, furyl), 7.79–7.90 m (2H, 5-H, 6-H), 8.01 d.d (1H, 8-H)
1609 (C=C); 1653 (C9=O); 3.97 d (1H, 2JHH 15.8 Hz, HB NCH2), 4.92 d (1H, 2JHH 15.8 Hz, HA NCH2), 5.49 s (1H, 1-H), 6.22 m
XIVd
1715 (C3=O)
(1H, furyl), 6.33 m (1H, furyl), 7.32–7.40 m (4H, Harom), 7.49–7.58 m (2H, 7-H, 1H, furyl), 7.79–
7.90 m (2H, 5-H, 6-H), 8.01 d.d (1H, 8-H)
Strong absorption bands in the region 1590–1750 cm–1 are given.
a
crystallization. The yield of the final product also
depends on the substituent in the benzene ring of the
initial aromatic aldehyde. Electron-withdrawing sub-
stituents favor formation of chromenopyrroles, while
aromatic aldehydes with electron-donating groups
gave lower yields.
intensity ratio and position of these bands depend on
the substituents, but the general pattern remains the
same for all compounds (Table 2). No absorption was
observed in the region 3200–3600 cm–1, indicating
participation of the OH and NH in the
cyclocondensation. In the 1H NMR spectra of IX–XIV
(Table 2), the 1-H proton resonated as a singlet at δ
6.30–6.70 ppm. The 5-H and 6-H protons gave rise to
a multiplet in the region δ 7.75–7.95 ppm, the 7-H
signal was a doublet of doublets at δ 7.50–7.60 ppm,
and the doublet at δ 8.00–8.10 ppm was assigned to 8-
H. Diastereotopic protons in the methylene group on
the N2 nitrogen atom gave two multiplets (X, XI, XIII)
or two doublets (XII, XIV).
The structure of the isolated compounds was
1
confirmed by their IR and H NMR spectra and
elemental analyses. The IR spectra of 1,2-
dihydrochromeno[2,3-c]pyrrole-3,9-diones in KBr
characteristically contained three absorption bands in
the region 1590–1720 cm–1: a medium-intensity band
at 1600–1620 cm–1 due to stretching vibrations of the
C=C bond, a strong band at 1640–1665 cm–1 belonging
to stretching vibrations of the C9=O carbonyl, and a
strong carbonyl band at 1695–1720 cm–1 (C3=O). The
Chromone derivatives IX–XIV are colorless
crystalline substances that are readily soluble in acetic
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 78 No. 12 2008