OUDI ET AL.
7
1H, J = 7.8 Hz, ArH), 3.40 (s, 3H, CH3), and 3.04 (s, 3H,
(dd, J = 3.3 Hz, J = 1.8 Hz, 1H, ArH), 6.01 (d, J = 3.0 Hz,
1H, ArH), 4.71 (s, 1H, CH), and 1.91 (s, 3H, CH3) ppm.
CH3) ppm.
4 | CONCLUSIONS
3.4.3 | 20-Amino-2,50-dioxo-2H,50H-spiro
(acenaphthylene-1,40-pyrano[3,2-c]chromene)-
30-carbonitrile (4j)
White solid; m.p: 288–291ꢀC; IR (KBr): νmax 3,404, 3,322,
2,962, 2,191, 1,712, 1,678, 1,650, 1,533, 1,488, 1,189,
992, and 785 cm−1 1H NMR (DMSO-d6, 300 MHz): δ 8.36
(d, 1H, J = 7.8 Hz, ArH), 7.99–8.07 (m, 5H, ArH), 7.89 (t,
1H, J = 7.8 Hz, ArH), 7.64–7.81 (m, 5H, ArH, NH2), 7.57
(t, 1H, J = 7.5 Hz, ArH), and 7.50 (d, 1H, J = 8.1 Hz,
ArH) ppm.
We have introduced QUIN as a new and efficient catalyst
for one-pot multicomponent synthesis of spirochromenes
and dihydropyranopyrazoles. The relatively simple protocols
offer a benign and sustainable route using solvent-free con-
ditions or a green solvent. Easy work-up procedure, short
reaction time, high yield of products, and no need of chro-
matographic process plus the use of QUIN as an effective,
and commercially available catalyst are other merits of this
protocol.
3.4.4 | Ethyl 70-amino-7-bromo-10,30-dimethyl-
2,20,40-trioxo-10,20,30,40-tetrahydrospiro
(indoline-3,50-pyrano[2,3-d]pyrimidine)-60-
carboxylate (41)
ACKNOWLEDGMENTS
We gratefully appreciate the financial support from the
Research Council of the University of Sistan and
Baluchestan.
White solid; m.p: 227–228ꢀC; IR (KBr): νmax 3,508,
3,339, 2,987, 1,748, 1,705, 1,721, 1,694, 1,643, 1,619,
ORCID
1,474, 1,385, 1,195, 976, and 771 cm−1
;
1H NMR
(DMSO-d6, 300 MHz): δ 10.41 (s, 1H, NH), 8.13 (s, 2H,
NH2), 7.26 (dd, J = 8.1 Hz, 1H, ArH), 7.20 (1H, d,
J = 1.8 Hz, ArH), 6.67 (d, 1H, J = 8.1 Hz, ArH), 3.46 (q,
2H, J = 7.2 Hz, OCH2) 3.41 (s, 3H, CH3), 3.03 (s, 3H,
CH3), and 0.87 (t, 3H, J = 7.2 Hz, CH3) ppm. 13C NMR
(DMSO-d6, 75 MHz): δ 179.4, 167.4, 159.7, 158.8, 151.7,
150.0, 144.0, 138.2, 130.5, 126.3, 112.7, 110.5,
89.3,76.01, 59.7, 47.6, 29.8, 28.1, and 13.60 ppm. MS m/z
(%): 478 (M + 1)+.
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3.4.5 | 6-Amino-4-(4-bromophenyl)-3-methyl-
1,4-dihydropyrano[2,3-c]pyrazole-
5-carbonitrile (8d)
White solid, m.p: 242–245ꢀC; IR (KBr): νmax 3,396, 3,233,
2,190, 1,642, 1,597, 797, and 754; 1H NMR (300 MHz,
DMSO-d6): δ 12.16 (s, 1H, NH), 6.95 (s, 2H, NH2), 7.53 (d,
2H, J = 8.4 Hz, ArH), 7.15 (d, 2H, J = 8.1 Hz, ArH), 4.64
(s, 1H, CH), and 1.81 (s, 3H, CH3) ppm.
3.4.6 | 6-Amino-4-(furan-2-yl)-3-methyl-
1,4-dihydropyrano[2,3-c]pyrazole-
5-carbonitrile (8i)
White solid, m.p: 230–233ꢀC; IR (KBr): νmax 3,357, 3,174,
1
2,924, 2,188, 1,705, 1,650, 1,601,1,405, and 752 cm−1; H
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NMR (300 MHz, DMSO-d6): δ 12.09 (s, 1H, NH), 7.53 (dd,
J = 2.8 Hz, J = 1.2 Hz, 1H, ArH), 6.88 (s, 2H, NH2), 6.37