A novel approach for the synthesis of N -arylpyrroles

Synlett

Volumn , Issue 20, 2009, Pages 3336-3340

  Dumitrascu, Florea ^a   Georgescu, Emilian ^b   Caira, Mino R ^c   Georgescu, Florentina ^b   Popa, Marcel ^a   Draghici, Bogdan ^a   Dumitrescu, Dan G ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Romania)

^b Oltchim Research Center   (Romania)

^c UNIVERSITY OF CAPE TOWN   (South Africa)

Author keywords

1,3 dipolar cycloaddition; N ylide; One pot reaction; Pyrroles; Pyrrolo 1,2 a quinazoline

Indexed keywords

1,2 EPOXYBUTANE; ALKANE DERIVATIVE; PYRROLE DERIVATIVE; PYRROLO[1,2 A]QUINAZOLINE DERIVATIVE; QUINAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; ONE POT SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 72149110620     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1218372     Document Type: Article

References (53)

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26. General Procedure for Obtaining the Bromide Salts 3 3-Methyl-4(3H)- quinazolin-4-one (1, 10 mmol) and 2-bromoacetophenone 2 (10 mmol) in EtOH (30 mL) was stirred under reflux for 20 h. The obtained precipitate was filtered and then recrystallized from MeOH. 1-(2-Phenyl-2-oxoethyl)-3-methyl-4(3H)- quinazolinon-1-ium Bromide Colorless crystals with mp 287289 C were obtained by recrystallization from MeOH; yield 81%. Anal. Calcd C17H15BrN2O2: N, 7.80. Found: N, 8.04. FT-IR: 1687, 1709, 2927 cm1. 1H NMR (300 MHz, CDCl3): d = 3.87 (s, 3 H, MeN), 6.34 (s, 2 H, CH2), 7.43 (d, 1 H, J = 8.5 Hz, H-8), 7.577.62 (m, 2 H, H-3,H-5), 7.747.97 (m, 1 H, H-4), 7.83 (t, 1 H, J = 7.8 Hz, H-6), 7.98 (dt, 1 H, J = 8.5, 1.65 Hz, H-7), 8.098.12 (m, 2 H, H-2, H-6), 8.53 (dd, 1 H, J = 7.8, 1.65 Hz, H-5), 9.88 (s, 1 H, H-2). 13C NMR (75 MHz, CDCl3): d = 36.9 (MeN), 58.7 (CH2), 117.4 (C-8), 128.9, 129.7 (C-5, C-2, C-3, C-5, C-6), 131.0 (C-6), 119.6, 132.6, 137.8 (C-4a, C-8a, C-1), 136.3 (C-4), 137.7 (C-7), 154.4 (C-2), 157.9 (CON), 190.4 (COAr).
27. General Procedure for Obtaining the Pyrroles 4 Quaternary salt (5 mmol) and dipolarophile (7.5 mmol) are heated under reflux in 30 mL 1,2-epoxybutane for 60 h. The obtained precipitate is filtered and then recrystallized from MeOH. Ethyl 2-(4-Fluorobenzoyl)-1-(2-methylaminocarbonylphenyl) pyrrole-4-carboxylate (4h) Colorless crystals with mp 158160 C were obtained by recrystallization from MeOH; yield 61%. Anal. Calcd C22H19FN2O4: N, 7.10. Found: N, 7.28. FT-IR: 1635, 1660, 1708, 3389 cm1. 1H NMR (300 MHz, CDCl3): d = 1.33 (t, 3 H, J = 7.1 Hz, MeCH2), 2.67 (d, 1 H, J = 4.9 Hz, MeNH), 4.30 (sext, 2 H, J = 9.5, 7.1 Hz, CH2), 6.66 (q, 1 H, J = 4.9 Hz, NH), 7.157.22 (m, 3 H, H-6, H-3, H-5), 7.26 (d, 1 H, J = 1.6 Hz, H-5), 7.417.52 (m, 2 H, H-4, H-5), 7.61 (d, 1 H, J = 1.6 Hz, H-3), 7.657.68 (m, 1 H, H-3), 7.98 (dd, 2 H, J = 8.8, 5.5 Hz, H-2, H-6).13C NMR (75 MHz, CDCl3): d = 14.4 (MeCH2), 26.6 (MeNH), 60.6 (CH2O), 115.7 (d, J = 21.9 Hz, C-3, C-5), 117.3 (C-4), 122.1 (C-5), 127.1 (C- 6), 128.9 (C-3), 129.4, 130.7 (C-4, C-5), 132.5, 133.5, 136.7 (C-2, C-1, C-2), 132.6 (d, J = 9.0 Hz, C-2, C-6), 133.4 (d, J = 3.0 Hz, C-1), 135.0 (C-3), 163.5 (COO), 167.7 (CONH), 166.0 (d, J = 245.9 Hz, C-4), 184.8 (COAr). Dimethyl 2-Benzoyl-1-(2-methylaminocarbonylphenyl)- pyrrole-3,4-dicarboxylate (4m) Colorless crystals with mp 163165 C were obtained by recrystallization from MeOH; yield 53%. Anal. Calcd C23H20N2O6: C, 65.71; H, 4.79; N, 6.66. Found: C, 65.97; H, 5.03; N, 6.51. FT-IR: 1649, 1651, 1724, 3285 cm1. 1H NMR (300 MHz, CDCl3): d = 2.72 (1 H, d, J = 4.9 Hz, MeNH), 3.29, 3.81 (6 H, 2 s, 2 MeO), 7.03 (1 H, q, J = 4.9 Hz, NH), 7.057.08 (1 H, m, H-6), 7.347.40, 7.457.52 (4 H, 2 m, H-3, H-5, H-4, H-5), 7.50 (1 H, s, H-5), 7.597.65 (1 H, m, H-4), 7.667.69 (1 H, m, H-3), 7.837.87 (2 H, m, H- 2,H-6).13C NMR (75 MHz, CDCl3): d = 26.7 (MeNH), 51.9, 52.0 (2 MeO), 115.4, 123.0, 132.9, 135.2, 135.4, 137.4 (C-2, C-3, C-4, C-1, C-1, C-2), 127.0, 129.1, 129.3, 130.8, 132.7 (C-5, C-3, C-4, C-5, C-6), 128.8, 129.5 (C-2, C-3, C-5, C-6), 134.1 (C-4), 162.8, 163.8, 167.2 (2 COO, CONH), 188.2 (COAr).
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52. Crystal Data for 4h C22H19FN2O4; colorless prism; M = 394.39, monoclinic, C2/c, a = 32.702 (1) , b = 7.6703 (3) , c = 18.6347 (6) , b = 123.376 (1), V = 3903.3 (2) 3, Z = 8, T = 100 (2) K, F000 = 1648, R1 = 0.0374, wR2 = 0.1028. CCDC 750004 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc. cam.ac.uk/data-request/cif. Crystal Data for 4m C23H20N2O6; colorless prism; M = 420.41, monoclinic, P21/c, a = 13.874 (3) , b = 9.111 (2) , c = 17.175 (3) , b = 105.53 (3), V = 2087.7 (8) 3, Z = 4, T = 173 (2) K, F000 = 880, R1 = 0.0401, wR2 = 0.1072. The CCDC deposition number is 750005.
53. Dimethyl 1-Benzoyl-4-methyl-1,3a-dihydro-5(4H)- pyrrolo[1,2-a] quinazoline-5-one-2,3-dicarboxylate (6m) Colorless crystals with mp 156158 C were obtained by recrystallization from MeOH; yield 51%. Anal. Calcd C23H20N2O6: C, 65.71; H, 4.79; N, 6.66. Found: C, 66.01; H, 5.68; N, 6.89. FT-IR: 1632, 1659, 1705, 3387 cm1. 1H NMR (300 MHz, CDCl3): d = 3.10 (s, 3 H, MeN), 3.54, 3.90 (s, 6 H, 2 CO2Me), 6.32 (d, 1 H, J = 6.0 Hz, H-1), 6.34 (d, 1 H, J = 8.0 Hz, H-9), 6.45 (d, 1 H, J = 6.0 Hz, H-3a), 6.93 (t, 1 H, J = 7.5 Hz, H-7), 7.22 (ddd, 1 H, J = 7.5, 1.6 Hz, H-8), 7.547.59 (m, 2 H, H-3, H-5), 7.677.72 (m, 1 H, H-4), 8.02 (dd, 1 H, J = 7.5, 1.6 Hz, H-6), 7.097.12 (m, 2 H, H- 2, H-6). 13C NMR (75 MHz, CDCl3): d = 29.4 (MeN), 52.7, 53.0 (CO2Me), 71.7 (C-3a), 79.6 (C-1), 114.5 (C-9), 120.9 (C-7), 129.1 (C-2, C-6), 129.2 (C-3, C-5), 129.5 (C-6), 133.8 (C-8), 134.6 (C-4), 117.6, 135.2, 137.7, 139.7, 143.11 (C-2, C-3, C-5, C-5a, C-1), 161.8, 163.3, 163.4 (3 CO), 195.2 (CO).