Direct Palladium-Catalyzed Arylations of Aryl Bromides. with 2/9-Substituted Pyrimido[5,4-b]indolizines
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1 Direct Palladium-Catalyzed Arylations of Aryl Bromides with 2/9-Substituted Pyrimido[5,4-b]indolizines Min Jiang, Ting Li, Linghua Meng, Chunhao Yang,* Yuyuan Xie*, and Jian Ding State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, SIBS, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Shanghai, P.R.China Supporting Information Contents General Methods Procedures for the Coupling Reaction Copies of 1 MR and 13 C MR of Compounds
2 General Methods Reagents (chemicals) were purchased from commercial sources (Alfa and Shanghai Chemical Reagent Company), and used without further purification. All reagents were stored in the presence of CaCl 2 in a desiccator under vacuum at room temperature and protected from light. Analytical thin layer chromatography (TLC) used was HSGF 254 ( mm thickness, Yantai Huiyou Company, China). All products were characterized by MR and MS. 1 H and 13 C MR spectra were obtained on Varian Mercury-300 and Varian Mercury-400 spectrometers with tetramethylsilane (TMS) as the internal standard (IS). Chemical shifts were reported in parts per million (ppm, δ) downfield from TMS. Proton coupling patterns are described as singlet (s), doublet (d), triplet (t), quartet (q), multiplet (m), and broad (br). Low- and high-resolution mass spectra (LRMS and HRMS) were obtained on a Finnigan MAT 95 spectrometer. Procedures for the Coupling Reaction General Procedure: A solution of 2-substituted pyrimido[5,4-b]indolizine (0.4 mmol), aryl bromide (0.48 mmol), KOAc (0.078g, 0.8 mmol) and Pd (PPh 3 ) 4 (0.023g, 5 mol%, 0.02 mmol) in HMPA (2 ml) was stirred at 100 o C for 10 min under argon atmosphere. To this solution was added water (0.073 g, 0.4 mmol), and the mixture was stirred at 100 o C for 8h. The mixture was poured into water (20 ml) and the organic compound was extracted with ethyl acetate (3 10 ml). The combined organic layers were dried with a 2 SO 4, concentrated and purified by flash column chromatography (petroleum ether/ethyl acetate) to give the desired product. 2
3 Characterization data: 2,5-Diphenylpyrimido[5,4-b]indolizine (3aa) Yellow solid,mp: H MR (300 MHz, CDCl 3 ): δ 9.51 (s, 1H), (d, J =7.2 Hz,1H), 8.62 (d, J = 7.8 Hz, 2H), (m, 3H), (m, 5H), 7.37 (t, J =7.2 Hz, 1H), 7.03(dd, J = 6, 8.7 Hz, 1H), 6.63 (t, J = 6.9 Hz, 1H); 13 C MR (100 MHz, CDCl 3 ): δ 155.5, 149.9, 144.7, 138.4, 133.6, 133.4,129.6, 129.2, , 127.9, 126.4, 125.8, 123.9, 118.4, 116.0, 110.0, 103.8; MS (EI, m/z): 321 [M] + ; HRMS (EI): Calcd. for C 22 H 15 3 [M] + : : Found: Phenyl-5-p-tolylpyrimido[5,4-b]indolizine (3ab) Yellow solid, mp: H MR (300 MHz, CDCl 3 ): δ 9.51 (s, 1H), (d, J = 6.9 Hz,1H), 8.63 (d, J = 7.5 Hz, 2H), 7.72 (d, J = 9.6 Hz, 1H), (m, 5H), 7.36 (d, J = 7.5, 2H), 7.06 (d, J = 6.9 Hz, 1H), 6.63 (t, J = 6 Hz, 1H), 2.46(s, 3H); 13 C MR (100 MHz, CDCl 3 ): δ 155.4, 149.9, 144.6, 138.4, 136.2, 133.2, 130.5, 129.9, 129.6, 129.2, 128.6, 128.5, 127.9, 125.6, 123.9, 118.6, 116.1, 110.0, 103.8, 21.2; MS (EI, m/z): 335 [M] + ; HRMS (EI): Calcd. for C 23 H 17 3 [M] + : ; Found:
4 5-(4-Methoxyphenyl)-2-phenylpyrimido[5,4-b]indolizine (3ac) O Red solid, mp: H MR (300 MHz, CDCl 3 ): δ 9.49 (s, 1H), 8.82 (d, J = 6.9 Hz,1H), (d, J = 7.8 Hz, 2H), 7.68 (d, J = 9.6 Hz, 1H), (m, 5H), 7.10 (d, J = 8.4, 2H), (m, 1H), 6.63 (t, J = 6.9Hz, 1H), 3.91 (s, 3H); 13 C MR (100 MHz, CDCl 3 ): δ 158.3, 155.3, 149.8, 144.5, 138.4, 133.1, 129.8, 129.7, 128.6, 127.9, 125.8,125.4, 123.9, 118.5, 116.1, 114.7, 109.9, 103.6, 55.4; MS (EI, m/z): 351 [M] + ; HRMS (EI): Calcd. for C 23 H 17 3 O [M] + : ; Found: Phenyl-5-(pyrimidin-5-yl)pyrimido[5,4-b]indolizine (3af) Yellow solid, mp: 238 dec. 1 H MR (300 MHz, CF 3 COOD): δ 9.94 (s, 2H), 9.91 (d, J = 1.2 Hz,1H), 9.79 (s, 1H), 9.22 (d, J = 5.1 Hz, 1H), 8.44 (d, J = 5.7 Hz, 2H), 8.12 (d, J = 6.9 Hz, 1H), 7.83 (t, J = 5.1 Hz, 2H), 7.77 (t, J = 5.1 Hz, 2H), 7.36 (t, J = 4.5 Hz, 1H); 13 C MR (100 MHz, CF 3 COOD): δ 157.5, 152.5, 150.2, 148.5, 143.2, 142.4, 136.1, 135.8, 132.2, 131.4, 130.3, 128.9, 126.4, 115.9, 95.5; MS (EI, m/z): 323 [M] + ; HRMS (EI): Calcd. for C 20 H 13 5 [M] + : ; Found: Phenyl-5-(quinolin-3-yl)pyrimido[5,4-b]indolizine (3ah) 4
5 Yellow solid, mp: H MR (300 MHz, CDCl 3 ): δ 9.55 (s, 1H), 9.30 (s, 1H), 8.88 (d, J = 7.5 Hz, 1H), 8.62 (d, J = 8.1 Hz, 2H), 8.37 (s, 1H), 8.17 (d, J = 8.4 Hz, 1H), 7.88 (d, J = 8.1 Hz, 1H), (m, 2H), (m, 4H), (m, 1H), 6.72 (t, J = 6.6 Hz, 1H); 13 C MR (100 MHz, CDCl 3 ): δ 156.1, 150.8, 149.5, 146.5, 145.1, 138.2, 134.1, 133.9, 129.8, 129.2, 129.1, 128.6, 128.4, 127.9, 127.5, 127.2, 126.9, 124.2, 117.8, 116.1, 110.5, 99.9; MS (EI, m/z): 372 [M] + ; HRMS (EI): Calcd. for C 25 H 16 4 [M] + : ; Found: (3-itrophenyl)-2-phenylpyrimido[5,4-b]indolizine (3ai) O 2 Yellow solid, mp: H MR (300 MHz, DMSO-d6): 9.63 (s, 1H), 9.03 (d, J = 7.2 Hz, 1H), 8.60 (d, J = 7.2 Hz, 2H), 8.46 (t, J = 1.5 Hz, 1H), (m, 2H), 7.91 (d, J = 9.3 Hz, 1H), 7.82 (t, J = 7.8 Hz, 1H), (m, 3H), 7.36 (dd, J = 9.3 Hz, 1H), 7.94 (t, J = 6.3 Hz, 1H); 13 C MR (100 MHz, CDCl 3 ): δ 156.1, 149.3, 149.0, 145.0, 138.1, 135.6, 134.1, 134.0, 130.1, 129.9, 128.6, 127.9, 127.4, 124.3, 122.8, 120.8, 117.6, 115.7, 110.6, 101.1; MS (EI, m/z): 366 [M] + ; HRMS (EI): Calcd. for C 22 H 14 4 O 2 [M] + : ; Found: Methyl-5-phenylpyrimido[5,4-b]indolizine (3ba) 5
6 Yellow solid, mp: H MR (300 MHz, CDCl 3 ): δ 9.35 (s, 1H), 8.67 (d, J = 6.9 Hz, 1H), (m, 3H), (m, 2H), (m, 1H), (m, 1H), 6.60 (td, J = 0.9, 6.9 Hz, 1H), 2.93 (s, 3H); 13 C MR (100 MHz, CDCl 3 ): δ 158.3, 149.5, 144.5, 133.5, 132.5, 129.2, 128.6, 126.4, 125.4, 123.6, 118.4, 115.3, 110.0, 103.5, 25.7; MS (EI, m/z): 259 [M] + ; HRMS (EI): Calcd. for C 17 H 13 3 [M] + : ; Found: Methyl-5-p-tolylpyrimido[5,4-b]indolizine (3bb) Yellow solid, mp: H MR (300 MHz, CDCl 3 ): δ 9.35 (s, 1H), 8.68 (td, J = 1.2, 7.5 Hz, 1H), (m, 1H), 7.55 (d, J = 7.8 Hz, 2H), 7.35 (d, J = 7.8 Hz, 2H), (m, 1H), 6.60 (td, J = 0.9, 6.3 Hz, 1H), 2.94 (s, 3H), 2.45 (s, 3H); 13 C MR (100 MHz, CDCl 3 ): δ 158.5, 149.9, 144.3, 136.0, 132.1, 130.6, 129.8, 129.1, 128.6, 128.5, 124.9, 123.5, 118.5, 115.3, 109.7, 103.3, 25.9, 21.2; MS (EI, m/z): 273 [M] + ; HRMS (EI): Calcd. for C 18 H 15 3 [M] + : ; Found: (4-Methoxyphenyl)-2-methylpyrimido[5,4-b]indolizine (3bc) O 6
7 Red solid, mp: H MR (300 MHz, CDCl 3 ): δ 9.32 (s, 1H), 8.66 (d, J = 7.2 Hz, 1H), 7.66 (d, J = 9 Hz, 1H), 7.56 (d, J = 7.8 Hz, 2H), 7.08 (d, J = 7.8 Hz, 2H), (m, 1H), 6.60 (t, J = 6.3 Hz, 1H), 3.89 (s, 3H), 2.96 (s, 3H); 13 C MR (100 MHz, CDCl 3 ): δ 158.4, 158.3, 149.8, 144.2, 132.0, 129.7, 125.9, 124.8, 123.5, 118.4, 115.3, 114.6, 109.7, 103.1, 55.3, 25.8; MS (EI, m/z): 289 [M] + ; HRMS (EI): Calcd. for C 18 H 15 3 O [M] + : ; Found: Methyl-5-(pyrimidin-5-yl)pyrimido[5,4-b]indolizine (3bf) Yellow solid, mp: 280 dec. 1 H MR (300 MHz, CF 3 COOD): δ 9.8 (s, 2H), 9.71 (d, J = 6.9 Hz, 2H), 9.02 (d, J = 5.1 Hz, 1H), 8.00 (d, J = 6.9 Hz, 1H), (m, 1H), 7.23 (d, J = 5.1 Hz, 1H), 3.17 (s, 3H); 13 C MR (100 MHz, CF 3 COOD): 157.7, 154.9, 150.2, 148.2, 142.7, 142.2, 135.8, 132.3, 126.3, 117.1, 116.0, 95.1, 21.9; MS (EI, m/z): 261 [M] + ; HRMS (EI): Calcd. for C 15 H 11 5 [M] + : ; Found: Methyl-5-(quinolin-3-yl)pyrimido[5,4-b]indolizine (3bh) Yellow solid, mp: H MR (300 MHz, CDCl 3 ): δ 9.42 (s, 1H), 9.28 (d, J = 2.1 Hz, 1H), 8.76 (d, J = 7.5 Hz, 1H), 8.36 (d, J = 1.8 Hz, 1H), 8.16 (d, J = 8.4 Hz, 1H), 7.88 (d, J = 8.4 Hz, 1H), (m, 2H), 7.62 (td, J = 1.2, 7.8 Hz, 1H), (m, 1H), 6.70 (td, J = 1.2, 7.5 Hz, 1H), 2.96 (s, 3H); 13 C MR (100 MHz, CDCl 3 ): δ 159.2, 150.9, 149.4, 146.5, 144.9, 133.9, 133.3, 129.3, 129.1, 7
8 128.4, 127.5, 127.2, 126.5, 123.9, 117.7, 115.4, 110.4, 99.6, 25.9; MS (EI, m/z): 310 [M] + ; HRMS (EI): Calcd. for C 20 H 14 4 [M] + : ; Found: Methyl-5-(3-nitrophenyl)pyrimido[5,4-b]indolizine (3bi) O 2 Yellow solid, mp: H MR (300 MHz, CDCl 3 ): 9.37 (s, 1H),8.76 (d, J = 7.8 Hz, 1H), 8.51 (t, J = 1.8 Hz, 1H), (m, 1H), 7.98 (td, J = 1.2, 7.8 Hz, 1H), (m, 2H), (m, 1H), 6.72 (td, J = 1.2, 7.5 Hz, 1H), 2.96 (s, 3H); 13 C MR (100 MHz, CDCl 3 ): δ 159.3, 149.3, 148.9, 144.8, 135.6, 134.1, 133.1, 130.1, 126.9, 123.9, 122.8, 120.7, 117.5, 115.0, 110.4, 100.6, 25.9; MS (EI, m/z): 304 [M] + ; HRMS (EI): Calcd. for C 17 H 12 4 O 2 [M] + : ; Found: (5-Phenylpyrimido[5,4-b]indolizin-2-yl)morpholine (3ca) O Yellow solid, mp: H MR (300 MHz, CDCl 3 ): δ 9.11 (s, 1H), 8.38 (d, J = 7.2 Hz, 1H), (m, 5H), 7.30 (t, J = 7.2, 1H), 6.80 (dd, J = 6.3, 9.3 Hz, 1H), 6.43 (t, J = 6.3 Hz, 1H), 3.92 (t, J = 4.5 Hz, 4H), 3.84 (t, J = 4.5 Hz, 4H); 13 C MR (100 MHz, CDCl 3 ): 151.2, 145.8, 134.2, 130.5, 129.0, 128.4, 125.9, 123.3, 123.0, 118.6, 110.9, 109.3, 103.5, 66.9, 45.1; MS (EI, m/z): 330 [M] + ; HRMS (EI): Calcd. for C 20 H 18 4 O [M] + : ; Found: (5-p-Tolylpyrimido[5,4-b]indolizin-2-yl)morpholine (3cb) 8
9 O Yellow solid, mp: H MR (300 MHz, CDCl 3 ): δ 9.11 (d, J = 5.1 Hz, 1H), 8.36 (t, J = 6.3 Hz, 1H), (m, 3H), 7.31 (d, J = 8.4 Hz, 2H), (m, 1H), 6.41 (t, J = 6.3 Hz, 1H), 3.90 (t, J = 4.5 Hz, 4H), 3.84 (t, J = 4.5 Hz, 4H), 2.43 (s, 3H); 13 C MR (100 MHz, CDCl 3 ): 157.4, 151.2, 145.7, 135.6, 134.2, 131.1, 130.3, 129.7, 129.0, 128.4, 128.3, 125.9, 123.0, 118.7, 118.6, 110.9, 109.2, 103.5, 66.9, 45.1, 21.1; MS (EI, m/z): 344 [M] + ; HRMS (EI): Calcd. for C 21 H 20 4 O [M] + : ; Found: (5-(4-Methoxyphenyl)pyrimido[5,4-b]indolizin-2-yl)morpholine (3cc) O O Red solid, mp: H MR (300 MHz, CDCl 3 ): δ 9.07 (s, 1H), 8.34 (d, J = 6.9 Hz, 1H), (m, 3H), 7.04 (dd, J = 3, 11.4 Hz, 2H), 6.74 (dd, J = 6.3, 9.6 Hz, 1H), 6.40 (t, J = 6.9 Hz, 1H), (m, 4H), 3.87 (s, 3H), (m, 4H); 13 C MR (100 MHz, CDCl 3 ): 157.9, 157.5, 151.2, 145.5, 130.0, 129.5, 126.5, 122.9, 122.7, 118.6, 114.5, 111.0, 109.0, 103.1, 66.9, 55.3, 45.1; MS (EI, m/z): 360 [M] + ; HRMS (EI): Calcd. for C 21 H 20 4 O 2 [M] + : ; Found: (5-(Pyrimidin-5-yl)pyrimido[5,4-b]indolizin-2-yl)morpholine (3cf) 9
10 O Red solid, mp: H MR (300 MHz, CDCl 3 ): δ 9.12 (s, 1H), 9.07 (s, 1H), 9.01 (s, 2H), 8.45 (d, J = 6.9 Hz, 1H), 7.55 (d, J = 9.6 Hz, 1H), 6.96 (dd, J = 6.6, 9.6 Hz, 1H), 6.56 (t, J = 6.6 Hz, 1H), 3.93 (t, J = 4.8 Hz, 4H), 3.84 (t, J = 4.8 Hz, 4H); 13 C MR (100 MHz, CDCl 3 ): 157.8, 155.6, 155.4, 150.5, 146.5, 131.5, 129.1, 125.3, 123.5, 117.3, 110.1, 109.9, 95.4, 66.8, 44.9; MS (EI, m/z): 332 [M] + ; HRMS (EI): Calcd. for C 18 H 16 6 O [M] + : ; Found: (5-(Quinolin-3-yl)pyrimido[5,4-b]indolizin-2-yl)morpholine (3ch) O Red solid, mp: H MR (300 MHz, CDCl 3 ): δ 9.24 (d, J = 1.8 Hz, 1H), 9.15 (s, 1H), 8.43 (td, J = 0.9, 5.4 Hz, 1H), 8.29 (d, J = 1.5 Hz, 1H), 8.14 (d, J = 6.3 Hz, 1H), 7.85 (dd, J = 0.9, 6 Hz, 1H), (m, 1H), (m, 2H), (m, 1H), (m, 1H), 3.93 (t, J = 3.6 Hz, 4H), 3.85 (t, J = 3.6 Hz, 4H); 13 C MR (100 MHz, CDCl 3 ): 157.8, 151.0, 150.9, 146.3, 146.2, 133.2, 131.3, 129.2, 128.7, 128.5, 127.8, 127.4, 127.0, 124.4, 123.3, 117.9, 110.7, 109.7, 99.7, 66.9, 45.0; MS (EI, m/z): 381 [M] + ; HRMS (EI): Calcd. for C 23 H 19 5 O [M] + : ; Found: (5-(3-itrophenyl)pyrimido[5,4-b]indolizin-2-yl)morpholine (3ci) 10
11 O O 2 Red solid, mp: H MR (300 MHz, CDCl 3 ): δ 9.10 (s, 1H), (m, 2H), 8.10 (dd, J = 0.9, 7.8 Hz, 1H), 7.91 (d, J = 7.8 Hz, 1H), 7.60 (dd, J = 8.1, 16.2 Hz, 2H), 6.93 (dd, J = 6.3, 9.6 Hz, 1H), 6.52 (t, J = 6.3 Hz,1H), 3.92 (t, J = 4.5 Hz, 4H), 3.84 (t, J = 4.5 Hz, 4H); 13 C MR (100 MHz, CDCl 3 ): 157.7, 150.7, 148.9, 146.2, 136.2, 133.8, 131.2, 129.9, 124.9, 123.4, 122.5, 120.2, 117.7, 110.4, 109.8, 100.8, 66.8, 44.9; MS (EI, m/z): 375 [M] + ; HRMS (EI): Calcd. for C 20 H 17 5 O 3 [M] + : ; Found: Methyl-2,5-diphenylpyrimido[5,4-b]indolizine (3da) Yellow solid, mp: H MR (300 MHz, CDCl 3 ): δ 9.48 (s, 1H), 8.55 (d, J = 7.5 Hz, 2H), (m, 3H), (m, 5H), 7.37 (t, J =7.2 Hz, 1H), 6.95 (dd, J = 6.6, 9.3 Hz, 1H), 6.37 (d, J = 6.0 Hz, 1H), 3.31 (s, 3H); 13 C MR (100 MHz, CDCl 3 ): 154.5, 149.2,146.9, 139.2, 138.7, 134.9, 133.6, 129.2, 129.0, 128.9, 128.4, 127.5, 126.3, 125.2, 116.3, 115.6, 110.9, 103.8, 22.3; MS (EI, m/z): 335 [M] + ; HRMS (EI): Calcd. For C 23 H 17 3 [M] + : ; Found: Methyl-2-phenyl-5-p-tolylpyrimido[5,4-b]indolizine (3db) 11
12 Yellow solid, mp: H MR (300 MHz, CDCl 3 ): δ 9.47 (s, 1H), 8.56 (d, J = 7.2 Hz, 2H), (m, 1H), (m, 5H), 7.35 (d, J = 7.8, 2H), 6.93 (dd, J = 6.3, 9.6Hz, 1H), 6.36 (d, J = 6.9 Hz, 1H), 3.30 (s, 3H), 2.46 (s, 3H); 13 C MR (100 MHz, CDCl 3 ): δ 154.5, 149.3, 146.9, 139.1, 138.8, 136.1, 134.9, 130.5, 129.8, 129.2, 128.9, 128.4, 127.6, 125.0, 116.4, 115.8, 110.8, 103.9, 22.3, 21.2; MS (EI, m/z): 349 [M] + ; HRMS (EI): Calcd. For C 24 H 19 3 [M] + : ; Found: Methyl-2-phenyl-5-(quinolin-3-yl)pyrimido[5,4-b]indolizine (3dd) Yellow solid, mp: H MR (300 MHz, CDCl 3 ): δ 9.54 (s, 1H), 9.29 (d, J = 2.4 Hz, 1H), 8.57 (d, J = 6.6 Hz, 2H), 8.37 (d, J = 2.1 Hz, 1H), 8.18 (d, J = 8.4 Hz, 1H), 7.88 (d, J = 8.1 Hz, 1H), (m, 2H), (m, 4H), 7.08 (dd, J =6.3, 9.6 Hz, 1H), 6.49 (t, J = 6.6 Hz, 1H), 3.79 (s, 3H); 13 C MR (100 MHz, CDCl 3 ): δ 154.8, 151.0, 148.5, 147.1, 146.4, 139.5, 139.5, 138.3, 135.6, 133.9, 129.4, 129.2, 128.9, 128.3, 128.2, 127.5, 127.4, 127.0, 126.3, 116.2, 114.8, 111.4, 99.8, 22.2; MS (EI, m/z): 386 [M] + ; HRMS (EI): Calcd. for C 26 H 18 4 [M] + : ; Found: Methyl-2-phenyl-5-(pyrimidin-5-yl)pyrimido[5,4-b]indolizine (3de) 12
13 Yellow solid, mp: H MR (300 MHz, CF 3 COOD): δ 9.76 (s, 2H), 9.69 (s, 1H), 9.63 (s, 1H), 8.22 (d, J = 5.4 Hz, 2H), 7.85 (d, J = 6.9 Hz, 1H), (m, 4H), 6.98 (d, J = 5.4 Hz, 1H), 3.38 (s, 3H); 13 C MR (100 MHz, CF 3 COOD): δ 159.5, 152.4, 152.1, 151.8, 146.6, 145.1, 142.6, 137.2, 137.0, 133.8, 133.0, 132.2, 130.2, 119.7, 118.7, 118.0, 116.8, 116.2, 97.1, 23.9; MS (EI, m/z): 337 [M] + ; HRMS (EI): Calcd. for C 21 H 15 5 [M] + : ; Found:
14 Copies of spectrum of Compounds: 2,5-Diphenylpyrimido[5,4-b]indolizine (3aa) PPM 14
15 2,5-Diphenylpyrimido[5,4-b]indolizine (3aa) 15
16 2,5-Diphenylpyrimido[5,4-b]indolizine (3aa) 16
17 2,5-Diphenylpyrimido[5,4-b]indolizine (3aa) 17
18 2,5-Diphenylpyrimido[5,4-b]indolizine (3aa) 18
19 2-Phenyl-5-p-tolylpyrimido[5,4-b]indolizine (3ab) PPM 19
20 2-Phenyl-5-p-tolylpyrimido[5,4-b]indolizine (3ab) 20
21 5-(4-Methoxyphenyl)-2-phenylpyrimido[5,4-b]indolizine (3ac) O PPM 21
22 5-(4-Methoxyphenyl)-2-phenylpyrimido[5,4-b]indolizine (3ac) 22
23 2-Phenyl-5-(pyrimidin-5-yl)pyrimido[5,4-b]indolizine (3af) PPM 23
24 2-Phenyl-5-(pyrimidin-5-yl)pyrimido[5,4-b]indolizine (3af) 24
25 2-Phenyl-5-(quinolin-3-yl)pyrimido[5,4-b]indolizine (3ah) PPM 25
26 2-Phenyl-5-(quinolin-3-yl)pyrimido[5,4-b]indolizine (3ah) 26
27 5-(3-itrophenyl)-2-phenylpyrimido[5,4-b]indolizine (3ai) O PPM 27
28 5-(3-itrophenyl)-2-phenylpyrimido[5,4-b]indolizine (3ai) 28
29 2-Methyl-5-phenylpyrimido[5,4-b]indolizine (3ba) PPM 29
30 2-Methyl-5-phenylpyrimido[5,4-b]indolizine (3ba) 30
31 2-Methyl-5-p-tolylpyrimido[5,4-b]indolizine (3bb) PPM 31
32 2-Methyl-5-p-tolylpyrimido[5,4-b]indolizine (3bb) 32
33 5-(4-Methoxyphenyl)-2-methylpyrimido[5,4-b]indolizine (3bc) O PPM 33
34 5-(4-Methoxyphenyl)-2-methylpyrimido[5,4-b]indolizine (3bc) 34
35 2-Methyl-5-(pyrimidin-5-yl)pyrimido[5,4-b]indolizine (3bf) PPM 35
36 2-Methyl-5-(pyrimidin-5-yl)pyrimido[5,4-b]indolizine (3bf) 36
37 2-Methyl-5-(quinolin-3-yl)pyrimido[5,4-b]indolizine (3bh) PPM 37
38 2-Methyl-5-(quinolin-3-yl)pyrimido[5,4-b]indolizine (3bh) 38
39 2-Methyl-5-(3-nitrophenyl)pyrimido[5,4-b]indolizine (3bi) O PPM 39
40 2-Methyl-5-(3-nitrophenyl)pyrimido[5,4-b]indolizine (3bi) 40
41 4-(5-Phenylpyrimido[5,4-b]indolizin-2-yl)morpholine (3ca) O PPM 41
42 4-(5-Phenylpyrimido[5,4-b]indolizin-2-yl)morpholine (3ca) 42
43 4-(5-p-Tolylpyrimido[5,4-b]indolizin-2-yl)morpholine (3cb) O PPM 43
44 4-(5-p-Tolylpyrimido[5,4-b]indolizin-2-yl)morpholine (3cb) 44
45 4-(5-(4-Methoxyphenyl)pyrimido[5,4-b]indolizin-2-yl)morpholine (3cc) O O PPM 45
46 4-(5-(4-Methoxyphenyl)pyrimido[5,4-b]indolizin-2-yl)morpholine (3cc) 46
47 4-(5-(Pyrimidin-5-yl)pyrimido[5,4-b]indolizin-2-yl)morpholine (3cf) O PPM 47
48 4-(5-(Pyrimidin-5-yl)pyrimido[5,4-b]indolizin-2-yl)morpholine (3cf) 48
49 4-(5-(Quinolin-3-yl)pyrimido[5,4-b]indolizin-2-yl)morpholine (3ch) O PPM 49
50 4-(5-(Quinolin-3-yl)pyrimido[5,4-b]indolizin-2-yl)morpholine (3ch) 50
51 4-(5-(3-itrophenyl)pyrimido[5,4-b]indolizin-2-yl)morpholine (3ci) O O PPM 51
52 4-(5-(3-itrophenyl)pyrimido[5,4-b]indolizin-2-yl)morpholine (3ci) 52
53 9-Methyl-2,5-diphenylpyrimido[5,4-b]indolizine (3da) PPM 53
54 9-Methyl-2,5-diphenylpyrimido[5,4-b]indolizine (3da) 54
55 9-Methyl-2-phenyl-5-p-tolylpyrimido[5,4-b]indolizine (3db) PPM 55
56 9-Methyl-2-phenyl-5-p-tolylpyrimido[5,4-b]indolizine (3db) 56
57 9-Methyl-2-phenyl-5-(quinolin-3-yl)pyrimido[5,4-b]indolizine (3dd) PPM 57
58 9-Methyl-2-phenyl-5-(quinolin-3-yl)pyrimido[5,4-b]indolizine (3dd) 58
59 9-Methyl-2-phenyl-5-(pyrimidin-5-yl)pyrimido[5,4-b]indolizine (3de) PPM 59
60 9-Methyl-2-phenyl-5-(pyrimidin-5-yl)pyrimido[5,4-b]indolizine (3de) 60
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