organic compounds
Ethyl 7-methyl-2-((1-methyl-1H-pyrrol-2-yl)methylene)-3-oxo-5-phenyl-3,5-dihydro-2H-thiazolo[3,2-a]pyrimidine-6-carboxylate
aWenzhou Medical College, School of Pharmacy, Wenzhou 325035, People's Republic of China
*Correspondence e-mail: proflxk@163.com
In the structure of the title compound, C22H21N3O3S, the thiazole ring forms dihedral angles of 88.83 (7) and 9.39 (9)°, respectively, with the benzene and pyrrole rings. The dihydropyrimidine ring adopts a flattened boat conformation. The olefinic double bond is in a Z conformation.
Related literature
For related structures, see: Hou (2009); Zhao et al. (2011). For background to the biological properties of fused thiazolo[3,2-a]pyrimidine derivatives, see: Ashok et al. (2007); Bahekar & Shinde (2004); Hurst & Hull (1961); Mehta et al. (2006); Shah & Desai (2007); Srivastava et al. (2006); Subudhi et al. (2007); Magerramov et al. (2006); Zhou et al. (2008).
Experimental
Crystal data
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Data collection: SMART (Bruker, 2002); cell SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536812041748/aa2075sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812041748/aa2075Isup2.hkl
In a typical procedure of one pot Biginelli reaction, sulfamic acid (0.4 mol) was added to a solution of substituted benzaldehyde (0.5 mol), ethyl acetylacetate (0.6 mol), and thiourea (0.75 mol) in ethanol and reflux at 351 K for 2 h. When the reaction was finished, the mixture was cooled to room temperature and filtered. The product ethyl 2-mercapto-4-methyl-6 -phenyl-1,6-dihydropyrimidine-5-carboxylate was washed with water, and then dried in vacuum as a white solid.
To a stirred solution of ethyl ] 2-mercapto-4-methyl-6-phenyl-1,6-dihydropyrimidine-5-carboxylate (2 mmol) and ethyl chloroacetate (2 mmol) in ethanol (10 ml) pyridine (2 mmol) was added.The reaction was heated at refluxing temperature for 4 h. Then 1-methyl-1H-pyrrole-2-carbaldehyde (2 mmol) and morpholine (2 mmol) was added to the mixture without further treatment until the reaction finished. The mixture was then cooled to room temperature, filtered and washed with water to obtain crude product. The resulting yellow solid was collected and recrystallized from acetic acid, then single crystals were grown in CH2Cl2/CH3OH mixture (2:1). Yield 45.6%.
1H NMR (DMSO-d6) δ: 1.111 (3H, m, 6–CH3), 4.030 (2H, m, 6–CH2), 2.380 (3H, s, N–CH3), 3.730 (3H, s, 7–CH3), 6.035 (H, s, 5–CH), 6.317 (1H, m, pyrrole), 6.576(1H, m, pyrrole), 7.213 (1H, m, pyrrole), 7.284–7.340 (5H, m, Ar—H), 7.625 (1H, s, =CH). ESI-MS m/z: 408.4 (M)+, 430.3 (M+Na)+, calcd for C22H21N3O3S 407.49.
The H atoms were positioned geometrically (C—H = 0.93 – 0.98 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).
Data collection: SMART (Bruker, 2002); cell
SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).Fig. 1. The molecular structure of the title compound, showing 30% displacement ellipsoids for the non-hydrogen atoms. Hydrogen atoms are drawn as spheres of arbitrary radius. |
C22H21N3O3S | F(000) = 856 |
Mr = 407.48 | Dx = 1.371 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 4867 reflections |
a = 11.8187 (10) Å | θ = 5.0–56.3° |
b = 10.2911 (9) Å | µ = 0.19 mm−1 |
c = 16.2290 (14) Å | T = 293 K |
β = 90.584 (2)° | Prismatic, red |
V = 1973.8 (3) Å3 | 0.32 × 0.24 × 0.16 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 3877 independent reflections |
Radiation source: fine-focus sealed tube | 3433 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
phi and ω scans | θmax = 26.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −14→14 |
Tmin = 0.814, Tmax = 1.000 | k = −12→11 |
10415 measured reflections | l = −20→19 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.109 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0574P)2 + 0.5784P] where P = (Fo2 + 2Fc2)/3 |
3877 reflections | (Δ/σ)max < 0.001 |
265 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
C22H21N3O3S | V = 1973.8 (3) Å3 |
Mr = 407.48 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 11.8187 (10) Å | µ = 0.19 mm−1 |
b = 10.2911 (9) Å | T = 293 K |
c = 16.2290 (14) Å | 0.32 × 0.24 × 0.16 mm |
β = 90.584 (2)° |
Bruker SMART CCD area-detector diffractometer | 3877 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | 3433 reflections with I > 2σ(I) |
Tmin = 0.814, Tmax = 1.000 | Rint = 0.020 |
10415 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.109 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.30 e Å−3 |
3877 reflections | Δρmin = −0.19 e Å−3 |
265 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.45859 (3) | 0.25287 (4) | 0.01131 (2) | 0.04128 (14) | |
N1 | 0.36364 (10) | 0.46192 (12) | 0.06560 (7) | 0.0318 (3) | |
N2 | 0.26786 (11) | 0.35881 (14) | −0.04481 (8) | 0.0402 (3) | |
N3 | 0.76832 (11) | 0.15037 (14) | 0.18041 (8) | 0.0413 (3) | |
O1 | 0.48083 (10) | 0.52724 (11) | 0.17107 (8) | 0.0471 (3) | |
O2 | 0.05024 (13) | 0.69653 (15) | −0.05111 (10) | 0.0735 (5) | |
O3 | 0.14144 (10) | 0.76092 (11) | 0.06154 (7) | 0.0473 (3) | |
C1 | 0.45910 (12) | 0.45135 (15) | 0.11618 (9) | 0.0337 (3) | |
C2 | 0.52334 (12) | 0.33419 (15) | 0.09404 (9) | 0.0343 (3) | |
C3 | 0.34879 (12) | 0.36725 (15) | 0.00763 (9) | 0.0338 (3) | |
C4 | 0.19135 (13) | 0.46391 (15) | −0.04784 (9) | 0.0362 (3) | |
C5 | 0.19370 (12) | 0.56033 (15) | 0.00841 (9) | 0.0336 (3) | |
C6 | 0.27014 (12) | 0.55164 (14) | 0.08448 (9) | 0.0316 (3) | |
H6 | 0.3014 | 0.6379 | 0.0965 | 0.038* | |
C7 | 0.20515 (11) | 0.50354 (15) | 0.15961 (9) | 0.0330 (3) | |
C8 | 0.16948 (14) | 0.59098 (18) | 0.21843 (10) | 0.0446 (4) | |
H8 | 0.1883 | 0.6784 | 0.2138 | 0.054* | |
C9 | 0.10566 (17) | 0.5486 (2) | 0.28426 (11) | 0.0588 (5) | |
H9 | 0.0809 | 0.6081 | 0.3233 | 0.071* | |
C10 | 0.07856 (16) | 0.4197 (2) | 0.29245 (11) | 0.0573 (5) | |
H10 | 0.0360 | 0.3919 | 0.3370 | 0.069* | |
C11 | 0.11433 (15) | 0.3322 (2) | 0.23496 (11) | 0.0520 (4) | |
H11 | 0.0967 | 0.2446 | 0.2406 | 0.062* | |
C12 | 0.17686 (14) | 0.37389 (17) | 0.16826 (10) | 0.0422 (4) | |
H12 | 0.2001 | 0.3141 | 0.1289 | 0.051* | |
C13 | 0.11228 (15) | 0.45209 (19) | −0.12025 (11) | 0.0485 (4) | |
H13A | 0.0502 | 0.5112 | −0.1137 | 0.073* | |
H13B | 0.0840 | 0.3648 | −0.1235 | 0.073* | |
H13C | 0.1520 | 0.4728 | −0.1699 | 0.073* | |
C14 | 0.12023 (13) | 0.67570 (16) | 0.00121 (10) | 0.0396 (4) | |
C15 | 0.07470 (16) | 0.87886 (19) | 0.05991 (13) | 0.0561 (5) | |
H15A | −0.0034 | 0.8591 | 0.0727 | 0.067* | |
H15B | 0.0768 | 0.9173 | 0.0054 | 0.067* | |
C16 | 0.1209 (2) | 0.9705 (3) | 0.12081 (18) | 0.0907 (9) | |
H16A | 0.1136 | 0.9345 | 0.1751 | 0.136* | |
H16B | 0.0799 | 1.0509 | 0.1176 | 0.136* | |
H16C | 0.1993 | 0.9861 | 0.1096 | 0.136* | |
C17 | 0.61539 (12) | 0.29575 (16) | 0.13690 (10) | 0.0371 (3) | |
H17 | 0.6411 | 0.3529 | 0.1773 | 0.045* | |
C18 | 0.67851 (12) | 0.17881 (16) | 0.12828 (10) | 0.0384 (4) | |
C19 | 0.66600 (15) | 0.07268 (18) | 0.07624 (12) | 0.0503 (4) | |
H19 | 0.6123 | 0.0643 | 0.0343 | 0.060* | |
C20 | 0.74750 (17) | −0.01876 (19) | 0.09753 (13) | 0.0572 (5) | |
H20 | 0.7581 | −0.0994 | 0.0729 | 0.069* | |
C21 | 0.80908 (15) | 0.03176 (18) | 0.16125 (12) | 0.0516 (4) | |
H21 | 0.8697 | −0.0091 | 0.1875 | 0.062* | |
C22 | 0.81581 (16) | 0.23339 (19) | 0.24420 (13) | 0.0548 (5) | |
H22A | 0.8705 | 0.1853 | 0.2760 | 0.082* | |
H22B | 0.7565 | 0.2628 | 0.2796 | 0.082* | |
H22C | 0.8518 | 0.3069 | 0.2192 | 0.082* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0416 (2) | 0.0415 (2) | 0.0407 (2) | 0.01238 (17) | −0.00433 (17) | −0.00727 (16) |
N1 | 0.0271 (6) | 0.0325 (7) | 0.0358 (6) | 0.0032 (5) | −0.0009 (5) | −0.0010 (5) |
N2 | 0.0418 (7) | 0.0412 (8) | 0.0373 (7) | 0.0070 (6) | −0.0067 (6) | −0.0036 (6) |
N3 | 0.0334 (7) | 0.0417 (8) | 0.0488 (8) | 0.0044 (6) | −0.0002 (6) | 0.0088 (6) |
O1 | 0.0408 (6) | 0.0430 (7) | 0.0573 (7) | 0.0047 (5) | −0.0145 (5) | −0.0128 (6) |
O2 | 0.0766 (10) | 0.0619 (9) | 0.0813 (10) | 0.0293 (8) | −0.0421 (8) | −0.0117 (8) |
O3 | 0.0500 (7) | 0.0418 (7) | 0.0499 (7) | 0.0171 (5) | −0.0098 (5) | −0.0021 (5) |
C1 | 0.0281 (7) | 0.0335 (8) | 0.0396 (8) | −0.0014 (6) | −0.0007 (6) | 0.0012 (6) |
C2 | 0.0296 (7) | 0.0346 (8) | 0.0388 (8) | 0.0004 (6) | 0.0019 (6) | 0.0010 (6) |
C3 | 0.0346 (7) | 0.0338 (8) | 0.0331 (7) | 0.0041 (6) | 0.0019 (6) | 0.0005 (6) |
C4 | 0.0334 (7) | 0.0393 (8) | 0.0359 (7) | 0.0015 (6) | −0.0023 (6) | 0.0039 (6) |
C5 | 0.0289 (7) | 0.0357 (8) | 0.0363 (7) | 0.0019 (6) | −0.0008 (6) | 0.0055 (6) |
C6 | 0.0283 (7) | 0.0288 (7) | 0.0376 (8) | 0.0036 (6) | −0.0016 (6) | −0.0014 (6) |
C7 | 0.0263 (7) | 0.0398 (8) | 0.0328 (7) | 0.0047 (6) | −0.0051 (6) | −0.0007 (6) |
C8 | 0.0474 (9) | 0.0451 (10) | 0.0413 (9) | 0.0062 (8) | −0.0028 (7) | −0.0075 (7) |
C9 | 0.0566 (11) | 0.0806 (15) | 0.0395 (9) | 0.0131 (10) | 0.0064 (8) | −0.0122 (9) |
C10 | 0.0463 (10) | 0.0845 (16) | 0.0412 (9) | 0.0007 (10) | 0.0076 (8) | 0.0094 (9) |
C11 | 0.0436 (9) | 0.0572 (11) | 0.0554 (10) | −0.0039 (8) | 0.0033 (8) | 0.0114 (9) |
C12 | 0.0403 (8) | 0.0430 (9) | 0.0433 (9) | 0.0009 (7) | 0.0033 (7) | −0.0006 (7) |
C13 | 0.0467 (9) | 0.0545 (11) | 0.0442 (9) | 0.0063 (8) | −0.0121 (7) | −0.0035 (8) |
C14 | 0.0358 (8) | 0.0402 (9) | 0.0427 (8) | 0.0044 (7) | −0.0033 (7) | 0.0062 (7) |
C15 | 0.0539 (11) | 0.0439 (10) | 0.0703 (12) | 0.0189 (8) | −0.0066 (9) | −0.0017 (9) |
C16 | 0.0925 (18) | 0.0751 (17) | 0.1037 (19) | 0.0376 (14) | −0.0330 (15) | −0.0384 (14) |
C17 | 0.0305 (7) | 0.0371 (8) | 0.0437 (8) | 0.0001 (6) | −0.0004 (6) | 0.0003 (7) |
C18 | 0.0294 (7) | 0.0393 (9) | 0.0465 (9) | 0.0029 (6) | 0.0007 (6) | 0.0054 (7) |
C19 | 0.0444 (9) | 0.0479 (10) | 0.0584 (11) | 0.0083 (8) | −0.0045 (8) | −0.0052 (8) |
C20 | 0.0566 (11) | 0.0425 (10) | 0.0725 (13) | 0.0140 (9) | 0.0016 (10) | −0.0040 (9) |
C21 | 0.0438 (9) | 0.0447 (10) | 0.0663 (12) | 0.0142 (8) | 0.0024 (8) | 0.0129 (9) |
C22 | 0.0479 (10) | 0.0532 (11) | 0.0628 (12) | 0.0022 (8) | −0.0167 (9) | 0.0072 (9) |
S1—C2 | 1.7515 (15) | C9—H9 | 0.9300 |
S1—C3 | 1.7525 (15) | C10—C11 | 1.367 (3) |
N1—C3 | 1.3644 (19) | C10—H10 | 0.9300 |
N1—C1 | 1.3927 (18) | C11—C12 | 1.385 (2) |
N1—C6 | 1.4747 (18) | C11—H11 | 0.9300 |
N2—C3 | 1.2767 (19) | C12—H12 | 0.9300 |
N2—C4 | 1.410 (2) | C13—H13A | 0.9600 |
N3—C21 | 1.350 (2) | C13—H13B | 0.9600 |
N3—C18 | 1.382 (2) | C13—H13C | 0.9600 |
N3—C22 | 1.451 (2) | C15—C16 | 1.467 (3) |
O1—C1 | 1.2103 (18) | C15—H15A | 0.9700 |
O2—C14 | 1.1986 (19) | C15—H15B | 0.9700 |
O3—C14 | 1.336 (2) | C16—H16A | 0.9600 |
O3—C15 | 1.448 (2) | C16—H16B | 0.9600 |
C1—C2 | 1.471 (2) | C16—H16C | 0.9600 |
C2—C17 | 1.345 (2) | C17—C18 | 1.424 (2) |
C4—C5 | 1.348 (2) | C17—H17 | 0.9300 |
C4—C13 | 1.499 (2) | C18—C19 | 1.388 (2) |
C5—C14 | 1.475 (2) | C19—C20 | 1.388 (3) |
C5—C6 | 1.525 (2) | C19—H19 | 0.9300 |
C6—C7 | 1.530 (2) | C20—C21 | 1.362 (3) |
C6—H6 | 0.9800 | C20—H20 | 0.9300 |
C7—C8 | 1.381 (2) | C21—H21 | 0.9300 |
C7—C12 | 1.383 (2) | C22—H22A | 0.9600 |
C8—C9 | 1.384 (3) | C22—H22B | 0.9600 |
C8—H8 | 0.9300 | C22—H22C | 0.9600 |
C9—C10 | 1.371 (3) | ||
C2—S1—C3 | 91.30 (7) | C7—C12—C11 | 120.65 (16) |
C3—N1—C1 | 116.64 (12) | C7—C12—H12 | 119.7 |
C3—N1—C6 | 119.93 (12) | C11—C12—H12 | 119.7 |
C1—N1—C6 | 122.05 (12) | C4—C13—H13A | 109.5 |
C3—N2—C4 | 116.54 (13) | C4—C13—H13B | 109.5 |
C21—N3—C18 | 108.92 (15) | H13A—C13—H13B | 109.5 |
C21—N3—C22 | 124.10 (15) | C4—C13—H13C | 109.5 |
C18—N3—C22 | 126.96 (14) | H13A—C13—H13C | 109.5 |
C14—O3—C15 | 116.02 (13) | H13B—C13—H13C | 109.5 |
O1—C1—N1 | 123.23 (14) | O2—C14—O3 | 121.64 (15) |
O1—C1—C2 | 127.04 (14) | O2—C14—C5 | 126.98 (16) |
N1—C1—C2 | 109.69 (12) | O3—C14—C5 | 111.37 (13) |
C17—C2—C1 | 122.10 (14) | O3—C15—C16 | 109.13 (16) |
C17—C2—S1 | 126.93 (13) | O3—C15—H15A | 109.9 |
C1—C2—S1 | 110.87 (10) | C16—C15—H15A | 109.9 |
N2—C3—N1 | 126.75 (14) | O3—C15—H15B | 109.9 |
N2—C3—S1 | 121.76 (12) | C16—C15—H15B | 109.9 |
N1—C3—S1 | 111.48 (10) | H15A—C15—H15B | 108.3 |
C5—C4—N2 | 122.14 (13) | C15—C16—H16A | 109.5 |
C5—C4—C13 | 126.79 (15) | C15—C16—H16B | 109.5 |
N2—C4—C13 | 111.07 (14) | H16A—C16—H16B | 109.5 |
C4—C5—C14 | 122.06 (14) | C15—C16—H16C | 109.5 |
C4—C5—C6 | 120.85 (13) | H16A—C16—H16C | 109.5 |
C14—C5—C6 | 117.05 (13) | H16B—C16—H16C | 109.5 |
N1—C6—C5 | 107.91 (11) | C2—C17—C18 | 128.30 (15) |
N1—C6—C7 | 110.27 (12) | C2—C17—H17 | 115.8 |
C5—C6—C7 | 111.47 (11) | C18—C17—H17 | 115.8 |
N1—C6—H6 | 109.0 | N3—C18—C19 | 106.40 (14) |
C5—C6—H6 | 109.0 | N3—C18—C17 | 121.26 (15) |
C7—C6—H6 | 109.0 | C19—C18—C17 | 132.26 (15) |
C8—C7—C12 | 118.85 (15) | C18—C19—C20 | 108.23 (17) |
C8—C7—C6 | 119.96 (15) | C18—C19—H19 | 125.9 |
C12—C7—C6 | 121.13 (13) | C20—C19—H19 | 125.9 |
C7—C8—C9 | 120.06 (18) | C21—C20—C19 | 107.12 (17) |
C7—C8—H8 | 120.0 | C21—C20—H20 | 126.4 |
C9—C8—H8 | 120.0 | C19—C20—H20 | 126.4 |
C10—C9—C8 | 120.59 (18) | N3—C21—C20 | 109.33 (16) |
C10—C9—H9 | 119.7 | N3—C21—H21 | 125.3 |
C8—C9—H9 | 119.7 | C20—C21—H21 | 125.3 |
C11—C10—C9 | 119.81 (17) | N3—C22—H22A | 109.5 |
C11—C10—H10 | 120.1 | N3—C22—H22B | 109.5 |
C9—C10—H10 | 120.1 | H22A—C22—H22B | 109.5 |
C10—C11—C12 | 120.04 (19) | N3—C22—H22C | 109.5 |
C10—C11—H11 | 120.0 | H22A—C22—H22C | 109.5 |
C12—C11—H11 | 120.0 | H22B—C22—H22C | 109.5 |
C3—N1—C1—O1 | −178.40 (14) | C5—C6—C7—C8 | −101.17 (16) |
C6—N1—C1—O1 | −11.8 (2) | N1—C6—C7—C12 | −43.80 (18) |
C3—N1—C1—C2 | −0.46 (18) | C5—C6—C7—C12 | 76.03 (17) |
C6—N1—C1—C2 | 166.11 (12) | C12—C7—C8—C9 | −0.6 (2) |
O1—C1—C2—C17 | 2.4 (2) | C6—C7—C8—C9 | 176.68 (15) |
N1—C1—C2—C17 | −175.41 (14) | C7—C8—C9—C10 | 0.9 (3) |
O1—C1—C2—S1 | 179.05 (14) | C8—C9—C10—C11 | −0.3 (3) |
N1—C1—C2—S1 | 1.22 (15) | C9—C10—C11—C12 | −0.6 (3) |
C3—S1—C2—C17 | 175.15 (15) | C8—C7—C12—C11 | −0.3 (2) |
C3—S1—C2—C1 | −1.27 (11) | C6—C7—C12—C11 | −177.55 (14) |
C4—N2—C3—N1 | 5.9 (2) | C10—C11—C12—C7 | 0.9 (3) |
C4—N2—C3—S1 | −173.22 (11) | C15—O3—C14—O2 | 0.3 (2) |
C1—N1—C3—N2 | −179.70 (15) | C15—O3—C14—C5 | 179.36 (14) |
C6—N1—C3—N2 | 13.4 (2) | C4—C5—C14—O2 | 2.3 (3) |
C1—N1—C3—S1 | −0.50 (16) | C6—C5—C14—O2 | −175.46 (18) |
C6—N1—C3—S1 | −167.38 (10) | C4—C5—C14—O3 | −176.79 (14) |
C2—S1—C3—N2 | −179.73 (14) | C6—C5—C14—O3 | 5.49 (19) |
C2—S1—C3—N1 | 1.03 (11) | C14—O3—C15—C16 | −170.47 (19) |
C3—N2—C4—C5 | −8.6 (2) | C1—C2—C17—C18 | 172.86 (15) |
C3—N2—C4—C13 | 170.92 (14) | S1—C2—C17—C18 | −3.2 (3) |
N2—C4—C5—C14 | 174.67 (14) | C21—N3—C18—C19 | −0.08 (18) |
C13—C4—C5—C14 | −4.7 (2) | C22—N3—C18—C19 | 178.08 (16) |
N2—C4—C5—C6 | −7.7 (2) | C21—N3—C18—C17 | 177.00 (14) |
C13—C4—C5—C6 | 172.92 (15) | C22—N3—C18—C17 | −4.8 (2) |
C3—N1—C6—C5 | −26.08 (17) | C2—C17—C18—N3 | −176.53 (15) |
C1—N1—C6—C5 | 167.78 (13) | C2—C17—C18—C19 | −0.3 (3) |
C3—N1—C6—C7 | 95.89 (15) | N3—C18—C19—C20 | 0.3 (2) |
C1—N1—C6—C7 | −70.25 (17) | C17—C18—C19—C20 | −176.32 (17) |
C4—C5—C6—N1 | 23.55 (19) | C18—C19—C20—C21 | −0.4 (2) |
C14—C5—C6—N1 | −158.71 (12) | C18—N3—C21—C20 | −0.2 (2) |
C4—C5—C6—C7 | −97.67 (16) | C22—N3—C21—C20 | −178.41 (17) |
C14—C5—C6—C7 | 80.07 (16) | C19—C20—C21—N3 | 0.4 (2) |
N1—C6—C7—C8 | 139.00 (14) |
Experimental details
Crystal data | |
Chemical formula | C22H21N3O3S |
Mr | 407.48 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 11.8187 (10), 10.2911 (9), 16.2290 (14) |
β (°) | 90.584 (2) |
V (Å3) | 1973.8 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.19 |
Crystal size (mm) | 0.32 × 0.24 × 0.16 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2002) |
Tmin, Tmax | 0.814, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10415, 3877, 3433 |
Rint | 0.020 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.109, 1.05 |
No. of reflections | 3877 |
No. of parameters | 265 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.30, −0.19 |
Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
Acknowledgements
This work was supported by the Zhejiang Provincial Natural Science Foundation of China (grants No. LY12H16003 and Y4110197) and the project of Wenzhou Sci & Tech Bureau (Y20100273). The X-ray crystallographic facility at the Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, is gratefully acknowledged for the data collection.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Thiazolinone and their derivatives have attracted continuing interest over the years because of their varied biological activities (Shah & Desai,2007), such as antifungal (Mehta et al., 2006), antibacterial (Subudhi et al., 2007), anti-tumor (Zhou et al., 2008), anti-HIV and anti-inflammatory (Srivastava et al., 2006). 3,4-Dihydropyrimidin-2(1H)-ones (DHPMs) are known for more than a century and have attracted considerable attention because of their wide spectrum of therapeutic and pharmacological properties. DHPMs have been used as antibacterial, antifungal (Ashok et al., 2007), antiviral (Hurst & Hull, 1961), anti-inflammatory (Bahekar & Shinde, 2004), antioxidative properties and noteworthy, as well as calcium channel modulators (Magerramov et al., 2006). Herein, we report in the present work based on the pharmacological principle of stacking, such biologically active groups as DHPMs was introduced to thiazolinone, with a view to get new compounds with better bioactivity.
In continuation of our studies on heterocyclic compounds, we report the crystal structure of the title compound. The fused thiazole ring has usual geometry as observed in other thiazolo[3,2-a]pyrimidine compounds (Hou, 2009; Zhao et al., 2011). The thiazole ring makes dihedral angles of 88.83 (7) and 9.39 (9)° with the benzene ring and pyrrole ring, respectively. The pyrimidine ring adopts a flattened boat conformation. The C2–C17 distance, 1.345 (2) Å, confirms this as a double bond and the molecule adopts a Z conformation with respect to this bond (Fig. 1).