Synthesis of Some Pyrido-Imidazophenazine Derivatives
1939
TABLE II Spectral Data for Selected Compounds
Comp. no.
IR (νmax/cm−1
)
1H-NMR (δ/ppm)
1
3400–3320 (NH2), 3098 C
H
6.26 (s, 4H, 2NH2), disappear by
(arom.), 1610–1480 (C C)
conj., 162 (C N)
deuteration with D2O, 6.92 (s, 2H,
Hrom.), 7.53 (m, 2H, arom.) and 7.88
(m, 2H, arom.)
2
4
3465 (NH) cyclic, 3120 (C H)
arom., 2920 ( CH) aliph.,
1610–1480 (C N) conj.,
1623 (C N)
4.6 (s, 2H, CH2-), 7.9 (m, 2H, arom.),
8.42 (m, 2H, arom.), 9.1 (s, 2H, arom.)
and 12.9 (br.(s), 1H, NH).
3120 (CH) arom., 2930 (CH)
aliph., 2210 (C≡N), 1890
2.6 (s, 6H, 2CH3), 7.4 (m, 5H, arom.),
7.86 (m, 2H, arom.); 8.38 (m, 2H,
arom.) and 9.12 (s, 2H, arom.)
(N
N ), 1624 (C N),
1616–1510 (C C) conj.
3480 (OH), 2220 (C≡N), 1620
(C N)
5b
6a
6.9 (s, 1H, arom.), 7.2 (br., 1H, OH); 7.4
(m, 5H, arom.); 7.8 (m, 2H, arom.); 8.3
(m, 2H, arom.) and 9.08 (s, 2H, arom.)
1.3 (t, 3H, CH3), 4.1–4.2 (m, 2H,
o-CH2CH3); 2.6 (s, 3H, CH3); 7.2 (br.,
1H, OH); 7.4 (m, 5H, arom.); 7.9 (m,
2H, arom.); 8.4 (m, 2H, arom.) and 9.1
(s, 2H, arom.)
3470 (OH), 1910 (N
N ),
1760 (C O) ester, 1623
(C N), 1158, 1193
(C
O C)
7
8
3300–3180 (NH2), 3100 (CH)
arom., 2210 (C≡N), 1620
(C N)
6.3 (s, 2H, NH2); 7.2 (s, 1H arom.); 7.4
(m, 5H, arom.); 7.84 (m, 2H, arom.),
8.37 (m, 2H, arom), 9.12 (s, 2H, arom.)
6.3 (s, 2H, NH2), 7.3 (m, 10H, arom.),
7.87 (m, 2H, arom.); 8.43 (m, 2H,
arom.) and 9.12 (s, 2H, arom.)
3390–3280 (NH2), 3098 (CH)
arom., 2210 (C≡N), 1910
(N
N ), 1624 (C N),
1610–1485 (C C) conj.
3100 (CH) arom., 2910 (CH)
aliph., 2210 (C≡N), 1760
(C O) ester, 1624 (C N),
9
1.4 (t, 3H, CH3); 4.2–4.3 (m, 2H,
OCH2CH3); 4.7 (s, 2H, CH2CN), 7.83
(m, 2H, arom.), 8.39 (m, 2H, arom.)
and 9.08 (s, 2H, arom.)
1160, 1195 (C
O C)
10
3098 (CH) arom., 2220 (C≡N),
3.6 (s, 2H, CH2); 7.4 (m, 5H, arom.); 7.84
(m, 2H, arom.); 8.41 (m, 2H, arom.);
and 9.12 (s, 2H, arom.)
1720 (C O), 1623 (C N)
Reaction of compound (2) with cyanoacetophenone, hydrazonyl-
acetophenone and/or ethyl chloroformate in acetic acid/acetic anhydride
under reflux condition give the corresponding pyrido[1,6-a]imidazo[4,5-
b]phenazine derivatives (7), (8) and/or (9) respectively.
Condensation reactions of (2) with different ketones such as acetone
and/or acetophenone in ethanol/piperidine under reflux condition, yield
the corresponding pyridoimidazophenazine derivatives (5a), and/or (10)
respectively. Finally compounds (3) and/or (7) can be coupled with dia-
zonium salts such as phenyldiazonium chloride in ethanol/sod. acetate
to afford the corresponding compounds (4) and/or (8) respectively.