# The Synthesis and Biological Evaluation of 2-(1H-Indol-3-yl)quinazolin-4(3H)-One Derivatives
## 3 Materials and Methods
#### Synthesis of 2-(1\(H\)-indol-3-yl)quinazolin-4(3\(h\))-one (**3a**) [80]
\({}^{1}\)H NMR (400 MHz, DMSO-\(d_{6}\)) \(\delta\) = 12.21 (brs, 1H), 11.85 (brs, 1H), 8.68-8.66 (m, 1H), 8.54 (brs, 1H), 8.37 (brs, 1H), 8.05-8.03 (m, 1H), 7.54-7.48 (m, 2H), and 7.25-7.20 (m, 2H) ppm; \({}^{13}\)C\({}^{[}\)H\(]\) NMR (100 MHz, DMSO-\(d_{6}\)) \(\delta\) = 160.7, 150.8, 149.0, 142.5, 136.8, 134.0, 129.4, 129.1, 125.4, 122.6, 122.3, 122.2, 120.9, 111.9, 108.4, and 89.1 ppm. HRMS (ESI) Calcd for C\({}_{16}\)H\({}_{11}\)IN\({}_{3}\)O [M + H]\({}^{+}\) 387.9941; Found 387.9947. N,N-dimethyl-1H-indole-3-carbothioamide (**7a**) was isolated as a by-product in the synthesis of 2-(1H-indol-3-yl)-6-iodoquinazolin-4(3H)-one (**3q**), 3-(1H-indol-3-yl)-2H-benzo[e][1,2,4] thiadiazine-1,1-dioxide (**3 af**), and 2-(1H-indol-3-yl)-5-phenyl-3,5-dihydro-4H-imidazol-4-one (**3 ag**) in 21%, 47%, and 50% yields, respectively. Yields of 0.056 g (21%) for **3q**, 0.125 g (47%) for **3 af**, and 0.133 g (50%) for **3 ag** were obtained and they were pale beige solids. Mp. \(\geq\) 180 \({}^{\circ}\)C, decomposition (petroleum ether/EtOAc). \({}^{1}\)H NMR (400 MHz, DMSO-\(d_{6}\)) \(\delta\) = 11.51 (brs, 1H), 7.68-7.62 (m, 2H), 7.43 (s, 1H), 7.12 (brs, 2H), and 3.42 (brs, 6H) ppm; \({}^{13}\)C\({}^{[}\)H\(]\) NMR (100 MHz, DMSO-\(d_{6}\)) \(\delta\) = 193.2, 135.5, 127.0, 124.8, 121.6, 120.3, 119.9, 118.3, 111.8, and 43.3 (brs, 2C) ppm. HRMS (ESI) Calcd for C\({}_{11}\)H\({}_{3}\)N\({}_{2}\)S [M + H]\({}^{+}\) 205.0794; Found 205.0792. (CCDC 2269768 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via. Available online: www.ccdc.cam.ac.uk/structures; accessed on 14 June 2023; for details, see Supplementary Materials). 2-(1H-Indol-2-yl)quinazolin-4(3H)-one (**3r**) [84]. A yield of 0.271 g (80%), 15 h, grey solid. Mp. \(\geq\) 326 \({}^{\circ}\)C, decomposition (EtOH, lit. [84] 302-304 \({}^{\circ}\)C). \({}^{1}\)H NMR (400 MHz, DMSO-\(d_{6}\)) \(\delta\) = 12.54 (brs, 1H), 11.73 (brs, 1H), 8.16 (brd, \(J\) = 7.6 Hz, 1H), 7.86-7.83 (m, 1H), 7.75-7.73 (m, 1H), 7.75-7.73 (m, 1H), 7.67-7.64 (m, 2H), 7.56-7.49 (m, 2H), 7.25-7.22 (m, 1H), and 7.09-7.05 (m, 1H) ppm; \({}^{13}\)C\({}^{[}\)H\(]\) NMR (100 MHz, DMSO-\(d_{6}\)) \(\delta\) = 161.6, 148.7, 146.5, 137.6, 134.5, 130.0, 127.4, 126.8, 126.1, 126.0, 123.9, 121.4, 121.1, 119.9, 112.3, and 104.9 ppm. 2-(Benzofuran-2-yl)quinazolin-4(3H)-one (**3s**) [85]. A yield of 0.235 g (69%), 6,5 h, beige solid. Mp. = 253-254 \({}^{\circ}\)C (EtOH) (lit. [84] 254-257 \({}^{\circ}\)C). \({}^{1}\)H NMR (400 MHz, DMSO-\(d_{6}\)) \(\delta\) = 12.69 (brs, 1H), 8.17 (brd, \(J\) = 7.6 Hz, 1H), 8.06 (s, 1H), 7.85-7.73 (m, 4H), 7.57-7.47 (m, 2H), and 7.37-7.34 (m, 1H) ppm; \({}^{13}\)C\({}^{[}\)H\(]\) NMR (100 MHz, DMSO-\(d_{6}\)) \(\delta\) = 161.4, 154.8, 148.3, 147.6, 144.2, 134.6, 127.4, 127.3, 126.93, 126.91, 125.9, 123.7, 122.5, 121.5, 111.7, and 110.1 ppm. 2-(Furan-2-yl)quinazolin-4(3H)-one (**3t**) [84]. A yield of 0.234 g (85%), 9 h, beige solid. Mp. = 221-222 \({}^{\circ}\)C (EtOH) (lit. [84] 210-212 \({}^{\circ}\)C). \({}^{1}\)H NMR (400 MHz, DMSO-\(d_{6}\)) \(\delta\) = 12.42 (brs, 1H), 8.12 (brd, \(J\) = 7.2 Hz, 1H), 7.98 (brs, 1H), 7.82-7.78 (m, 1H), 7.69-7.67 (m, 1H), 7.62 (d, \(J\) = 3.2 Hz, 1H), 7.50-7.47 (m, 1H), and 6.74-6.73 (m, 1H) ppm; \({}^{13}\)C\({}^{[}\)H\(]\) NMR (100 MHz, DMSO-\(d_{6}\)) \(\delta\) = 161.4, 148.6, 146.4, 146.1, 143.9, 134.5, 127.1, 126.3, 125.8, 121.1, 114.3, and 112.4 ppm. 2-(5-Methylfuran-2-yl)quinazolin-4(3H)-one (**3u**) [86]. A yield of 0.209 g (7%), 9 h, brown solid. Mp. = 195-196 \({}^{\circ}\)C (EtOH) (lit. [86] 191-192 \({}^{\circ}\)C).