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Organic & Biomolecular Chemistry
7.54–7.45 (m, 5H), 2.32 (s, 3H); 13C NMR (100 MHz, CDCl3): CDCl3): δ 154.9, 150.0, 142.9, 136.9, 134.6, 131.8, 130.1, 129.5,
δ 153.8, 149.1, 142.4, 139.0, 135.6, 132.1, 131.4, 131.3, 130.0, 128.87, 128.81, 128.7, 128.6, 128.2, 127.9, 127.5, 126.8, 125.9,
128.5, 127.5, 127.2, 118.0, 117.8, 18.2; IR (KBr) (cm−1): 125.5, 125.3, 122.4, 122.2, 112.4; IR (KBr) (cm−1): 1732, 1637;
1730, 1629; HRMS (ESI, m/z) calcd for C15H11N5OBr 356.0147 HRMS (ESI, m/z) calcd for C22H13N5ONa386.1018 (M + Na),
(M + H), found 356.0149.
found 386.1033.
3-(2,3-Dimethylphenyl)-7-methoxytetrazolo[5,1-b]quinazolin-
7-Fluoro-3-(1-naphthyl)tetrazolo[5,1-b]quinazolin-9(3H)-one
9(3H)-one (9a). Yellow solid, yield 60% (96 mg), mp: (17a). Pale yellow solid, yield 48% (79 mg), mp: 360–365 °C, 1H
214–216 °C, 1H NMR (500 MHz, CDCl3): δ 7.79 (d, J = 3 Hz, NMR (400 MHz, CDCl3): δ 8.16–8.11 (m, 2H), 8.03 (d, J =
1H), 7.59 (d, J = 9 Hz, 1H), 7.43–7.40 (m, 2H), 7.35–7.32 (m, 7.6 Hz, 1H), 7.80 (d, J = 7.2 Hz, 1H), 7.72–7.68 (m, 1H),
2H), 3.94 (s, 3H), 2.42 (s, 3H), 2.14 (s, 3H); 13C NMR (100 MHz, 7.66–7.57 (m, 4H), 7.54–7.50 (m, 1H); 13C NMR (100 MHz,
CDCl3): δ 156.9, 154.8, 145.0, 141.3, 139.5, 134.4, 132.8, 131.5, CDCl3): δ 160.7, 158.2, 154.2, 146.8, 134.7, 132.0, 129.1, 129.0,
128.2, 127.1, 126.8, 125.1, 117.0, 106.1, 56.0, 20.5, 14.8; IR 128.8, 128.5, 128.4, 127.5, 125.8, 125.3, 125.1, 124.8, 122.0,
(KBr) (cm−1): 1710, 1637; HRMS (ESI, m/z) calcd for 117.7, 117.6, 112.4, 112.1; IR (KBr) (cm−1): 1725, 1631; HRMS
C17H15N5O2Na344.1123 (M + Na), found 344.1129.
(ESI, m/z) calcd for C18H10N5OFNa 354.0767 (M + Na), found
7-Methoxy-3-(4-methoxyphenyl)tetrazolo[5,1-b]quinazolin-9 354.0788.
(3H)-one (11a). Pale yellow solid, yield 72% (116 mg), mp:
7-Chloro-3-(1-naphthyl)tetrazolo[5,1-b]quinazolin-9(3H)-one
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205–207 °C, H NMR (400 MHz, CDCl3): δ 8.10 (d, J = 8.8 Hz, (18a). Pale yellow solid, yield 56% (97 mg), mp: 220–222 °C, 1H
2H), 7.76 (d, J = 2.8 Hz, 1H), 7.67 (d, J = 9.2 Hz, 1H), 7.44 (dd, NMR (400 MHz, CDCl3): δ 8.45 (d, J = 2.4 Hz, 1H), 8.16 (d, J =
J = 9.2, 2.8 Hz, 1H), 7.10 (d, J = 9.2 Hz, 2H), 3.94 (s, 3H), 3.89 8 Hz, 1H), 8.03 (d, J = 7.6 Hz, 1H), 7.80 (dd, J = 7.2, 1.2 Hz,
(s, 3H); 13C NMR (100 MHz, CDCl3): δ 159.8, 157.0, 154.6, 1H), 7.72–7.68 (m, 2H), 7.66–7.57 (m, 3H), 7.55 (d, J = 8.8 Hz,
144.8, 128.3, 127.3, 127.1, 122.3, 117.1, 115.0, 106.1, 56.0, 55.8; 1H); 13C NMR (100 MHz, CDCl3): δ 153.9, 148.7, 143.0, 136.4,
IR (KBr) (cm−1): 1708, 1630; HRMS (ESI, m/z) calcd for 134.6, 132.0, 130.5, 128.87, 128.82, 128.4, 127.5, 126.9, 125.8,
C16H13N5O3Na 346.0916 (M + Na), found 346.0911.
125.35, 125.31, 122.0, 117.7; IR (KBr) (cm−1): 1729, 1635;
7-Bromo-3-(4-bromophenyl)tetrazolo[5,1-b]quinazolin-9(3H)- HRMS (ESI, m/z) calcd for C18H11N5OCl 348.0652 (M + H),
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one (13a). White solid, yield 30% (63 mg), mp: 232–234 °C, H found 348.0677.
NMR (400 MHz, CDCl3): δ 8.57 (d, J = 2.4 Hz, 1H), 8.20 (AAlBBl
7-Bromo-3-(1-naphthyl)tetrazolo[5,1-b]quinazolin-9(3H)-one
pattern J = 8.8 Hz, 2H), 7.90 (dd, J = 8.8, 2.4 Hz, 1H), 7.75 (19a). White solid, yield 42% (82 mg), mp: 224–226 °C, 1H
(AAlBBl pattern J = 8.8 Hz, 2H), 7.64 (d, J = 8.8 Hz, 1H); NMR (400 MHz, CDCl3): δ 8.61 (d, J = 1.6 Hz, 1H), 8.15 (d, J =
13C NMR (125 MHz, CDCl3): δ 153.4, 148.6, 141.0, 139.3, 133.2, 8.4 Hz, 1H), 8.03 (d, J = 7.6 Hz, 1H), 7.84–7.79 (m, 2H), 7.70 (t,
133.1, 130.2, 128.7, 122.7, 121.6, 118.4, 118.2; IR (KBr) (cm−1): J = 8 Hz, 1H), 7.66–7.57 (m, 3H), 7.48 (d, J = 8.8 Hz, 1H);
1722, 1631; HRMS (ESI, m/z) calcd for
C
14H7N5OBr2Na 13C NMR (100 MHz, CDCl3): δ 153.8, 149.0, 143.1, 139.1, 134.6,
441.8915 (M + Na), found 441.8904.
132.1, 130.1, 128.87, 128.80, 128.5, 128.4, 127.5, 125.8,
7-Chloro-3-(4-chlorophenyl)tetrazolo[5,1-b]quinazolin-9(3H)- 125.3, 122.0, 118.1, 117.9; IR (KBr) (cm−1): 1731, 1627; HRMS
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one (14a). White solid, yield 58% (96 mg), mp: 207–209 °C, H (ESI, m/z) calcd for C18H11N5OBr 392.0147 (M + H), found
NMR (500 MHz, CDCl3): δ8.40 (d, J = 1.6 Hz, 1H), 8.25 (AAlBBl 392.0128.
pattern J = 9.0 Hz, 2H), 7.77 (dd, J = 8.5, 2.5 Hz, 1H), 7.70 (d,
3-(2,6-Dimethylphenyl)tetrazolo[5,1-b]quinazolin-9(3H)-one
J = 9.0 Hz, 1H), 7.60 (AAlBBl pattern J = 9.0 Hz, 2H), 13C NMR (20a). White solid, yield 76% (110 mg), mp: 197–199 °C, 1H
(125 MHz, CDCl3): δ 153.6, 148.2, 141.0, 136.6, 134.8, 132.7, NMR (400 MHz, CDCl3): δ 8.48 (dd, J = 8, 1.2 Hz, 1H),
131.0, 130.1, 128.5, 127.0, 121.3, 117.8; IR (KBr) (cm−1): 7.81–7.77 (m, 1H), 7.65 (dd, J = 8.4, 0.8 Hz, 1H), 7.46–7.42 (m,
1719, 1630; HRMS (ESI, m/z) calcd for
353.9925 (M + Na), found 353.9950.
C
14H7N5OCl2Na 2H), 7.27 (d, J = 9.2 Hz, 2H); 13C NMR (100 MHz, CDCl3):
δ 155.0, 150.4, 142.2, 137.0, 135.9, 131.6, 130.5, 129.2, 127.9,
3-(1-Naphthyl)tetrazolo[5,1-b]quinazolin-9(3H)-one
(15a). 126.8, 124.7, 116.6, 18.0; IR (KBr) (cm−1): 1729, 1635; HRMS
White solid, yield 70% (109 mg), mp: 234–236 °C, 1H NMR (ESI, m/z) calcd for C16H13N5OK 330.0757 (M + K), found
(500 MHz, CDCl3): δ 8.51(dd, J = 8.5, 1.5 Hz, 1H), 8.15 (d, J = 330.0734.
8.0 Hz, 1H), 8.04–8.02 (m, 1H), 7.82–7.76 (m, 2H), 7.72–7.69
3-p-Tolyltetrazolo[5,1-b]quinazolin-9(3H)-one (21a) & 7-methyl-
(m, 1H), 7.65–7.57 (m, 4H), 7.48–7.44 (m, 1H); 13C NMR 3-phenyltetrazolo[5,1-b]quinazolin-9(3H)-one (22a). The ratio
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(125 MHz, CDCl3): δ 155.0, 150.1, 142.9, 136.0, 134.7, 131.9, (by H NMR) of the starting material mixture (21 and 22) – 1
128.9, 128.8, 128.6, 128.3, 128.0, 127.5, 126.8, 125.8, 125.3, (21) : 0.83 (22).
124.9, 122.1, 116.7; IR (KBr) (cm−1): 1728, 1630; HRMS (ESI,
m/z) calcd for C18H12N5O 314.1042 (M + H), found 314.1062.
An inseparable mixture of 21a and 22a (ratio 1 : 0.80): white
solid, yield 71% (98 mg), mp: 123–125 °C, H NMR (400 MHz,
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11-(1-Naphthyl)benzo[h]tetrazolo[5,1-b]quinazolin-7(11H)- CDCl3): δ 8.45 (d, J = 8.0 Hz, 1H), 8.28–8.26 (m, 1.67H), 8.22 (s,
one (16a). White solid, yield 75% (136 mg), mp: 224–226 °C, 0.78H), 8.10 (d, J = 8.4 Hz, 1.96H), 7.83–7.80 (m, 1H), 7.76–7.73
1H NMR (400 MHz, CDCl3): δ 8.73 (dd, J = 8.4, 0.4 Hz, 1H), (m, 1H), 7.64–7.59 (m, 3.34H), 7.50–7.42 (m, 1.71H), 7.40 (d,
8.35 (d, J = 8.3 Hz, 1H), 8.19 (d, J = 8.4 Hz, 1H), 8.07 (d, J = 8.0 J = 8.0 Hz, 2.23H), 2.49 (s, 2.42H), 2.45 (s, 3H); 13C NMR
Hz, 1H), 7.93–7.88 (m, 2H), 7.79–7.73 (m, 3H), 7.70–7.64 (m, (100 MHz, CDCl3): δ 154.7, 150.0, 147.8, 139.1, 137.7, 137.6,
2H), 7.62–7.58 (m, 1H), 7.54–7.50 (m, 1H); 13C NMR (100 MHz, 136.0, 135.9, 135.2, 134.4, 131.8, 130.3, 129.8, 128.8, 128.7,
8634 | Org. Biomol. Chem., 2018, 16, 8629–8638
This journal is © The Royal Society of Chemistry 2018