2-amino-4-(p-tolyl)-4H-pyrano[3,2-h]quinoline-3-carbonitrile (4e)

White solid, yield; 90%, IR (KBr, υ_max cm⁻¹); 3495 (NH₂ str), 3035 (-CH str), 2223 (-CN), 1587 (-C=N str), 1149 (-C-O-C- str); ¹H NMR (CDCl₃-400 MHz, δ ppm); 7.7 (d, Ar-H), 7.3 - 7.4 (m, Ar-H), 7.2 - 7.3 (d, Ar-H), 7.0 (d, Ar-H), 6.8 - 6.9 (d, Ar-H),7.6 (s, NH₂), 6.6 - 6.7 (d, Ar-H), 6.5 (d, Ar-H), 5.2 - 5.3 (s, CH-pyran ring), 2.5 (s, 3H, CH₃); ESMS: 314 [M + 1].

6

2-amino-4-(4-chlorophenyl)-4H-pyrano[3,2-h]quinoline-3-carbonitrile(4f)

White solid, yield; 90%, IR (KBr, υ_max cm⁻¹); 3421 (NH₂ str), 3097 (-CH str), 2225 (-CN), 1637 (-C=N str), 1094 (-C-O-C- str); ¹H NMR (CDCl₃-400 MHz, δ ppm); 7.8 - 7.9 (d, Ar-H), 7.7 (d, Ar-H), 7.5 (d, Ar-H), 7.3 (d, Ar-H), 7.1 - 7.2 (d, Ar-H), 7.0 (s, NH₂), 6.5 - 6.7 (d, Ar-H), 6.4 (d, Ar-H), 5.1 - 5.2 (d, CH-pyran ring); ESMS: 334 [M + 1].

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2-amino-4-(3-hydroxy-4-methoxyphenyl)-4H-pyrano[3,2-h]quinoline-3-carbonitrile (4g)

Lemon yellow solid, yield; 88%, IR (KBr, υ_max cm⁻¹); 3394 (NH₂ str), 3082 (-CH str), 2228 (-CN), 1619 (-C=N str), 1281 (-C-O-C- str); ¹H NMR (CDCl₃-400 MHz, δ ppm); 7.5 (d, Ar-H), 7.2 - 7.3 (s, NH₂), 6.9 (d, Ar-H), 6.6 - 6.7 (m, Ar-H), 6.5 - 6.6 (d, Ar-H), 6.4 - 6.5 (d, Ar-H), 6.3 - 6.4 (d, Ar-H), 6.0 (s, Ar-H), 5.5 - 5.7 (s, OH proton), 4.7 - 4.9 (s, CH-pyran ring), 4.0 (s, OCH₃); ESMS: 346 [M + 1].