貳、 一鍋化合成 2,4,5-三取代三唑化合物
以表 2. 4 Entry 1 為例
秤取3-硝基硫色烯 (0.1347 g，0.5 mmol) 及疊氮化鈉 (0.0390 g，
後，加入碳酸銫 (0.4887 g，1.5 mmol)、1-氟-2-硝基苯 (0.1166 mL，1.1 mmol) 及二甲基亞碸 (1 mL)，在氧氣下反應，並以TLC追蹤反應，當 反應結束後利用二氯甲烷萃取，再以水萃取三次，收機有機層並以無 水硫酸鎂除水，所得混合物經由乙酸乙酯/正己烷管柱層析分離，即可 得橘色油狀物。秤重為0.1885 g，產率為72%。
2-5、參考文獻
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2-6、光譜資料 δ 186.1, 150.2, 145.5, 144.8, 143.9, 138.1, 137.5, 136.0, 135.2, 133.9, 133.6, 133.2, 132.3, 131.9, 131.1, 131.0, 130.6, 130.4, 130.0, 128.7, 128.5, 125.9, 125.5, 125.2, 125.1; HRMS (EI) calcd. 184.4, 162.6, 160.1, 149.5, 145.9, 144.9, 143.9, 138.2, 137.6, 135.1, 134.8 (d, JC-F = 8.8 Hz), 133.7, 133.2, 132.3, 131.9, 131.7, 131.2, 130.9, 130.7, 130.1, 128.7, 126.1, 125.8, 125.7, 125.6, 125.2(d, JC-F = 6.1 Hz), 124.2 (d, JC-F = 3.5 Hz), 116.7 (d, JC-F = 21.7 Hz); HRMS (EI) calcd. for C27H16F N5O5S [M+Na]+ 564.0754, found 564.0767.
H-1,2,3-triazol-4-yl)methanone (4c) 186.4, 149.9, 145.4, 145.0, 143.9, 138.4, 137,5, 136.8, 135.1, 133.7, 133.2, 132.4, 132.4, 132.2, 131.9, 131.3, 131.2, 131.0, 130.5, 130.5, 129.0, 126.6, 126.2, 125.6, 125.2, 125.1; HRMS (EI) calcd. for C27H16ClN5O5S [M+Na]+ 580.0458, found 138.8, 138.5, 137.5, 135.2, 133.8, 133.3, 132.4, 132,2, 131.9, 131.4, 131.3, 131.0, 130.6, 130.3, 129.0, 127.2, 126.3, 125.6, 125.2, 125.1, 125.0, 120.5; HRMS (EI) calcd. for C27H16BrN5O5S [M+Na]+ 623.9953, found 623.9980.
(4-fluorophenyl)(2-(2-nitrophenyl)-5-(2-((2-nitrophenyl)thio)phenyl)-2 131.7, 131.1, 130.8, 130.6, 130.0, 128.7, 125.8, 125.5, 125.1 (d, JC-F = 2.1 Hz), 115.8 (d, JC-F = 129.0, 128.8, 125.9, 125.6, 125.2, 125.2; HRMS (EI) calcd. for C27H16Cl N5O5S [M+Na]+ 580.0458, found 580.0470.
(2-methoxyphenyl)(2-(2-nitrophenyl)-5-(2-((2-nitrophenyl)thio)phenyl) 145.0, 144.0, 138.8, 137.5, 135.6, 133.9, 133.7, 133.1, 132.4, 132.2, 131.2, 131.1, 131.0, 130.4, 129.9, 129.0, 127.4, 126.3, 125.6, 125.1, 124.9, 120.4, 111.6, 55.8; HRMS (EI) calcd. for 129.4, 128.5, 125.9, 125.4, 125.1, 125.0, 123.2, 120.8, 113.8, 55.5; HRMS (EI) calcd. for C28H19N5O6S [M+Na]+ 576.0953, found 576.0970.
(4-methoxyphenyl)(2-(2-nitrophenyl)-5-(2-((2-nitrophenyl)thio)phenyl) 164.4, 150.0, 145.9, 144.8, 143.8, 138.2, 137.5, 135.3, 133.6, 133.2, 132.9, 132.3, 132.0, 131.0, 131.0, 130.6, 129.8, 129.0, 125.8, 125.5, 125.2, 125.0, 113.9, 55.7; HRMS (EI) calcd. For 150.1, 147.4, 145.6, 144.8, 143.8, 138.2, 137.5, 135.3, 133.6, 133.2, 132.3, 132.2, 132.0, 131.1, 130.8, 130.6, 130.0, 128.7, 125.9, 125.5, 125.2, 125.1, 124.9, 14.9; HRMS (EI) calcd. for C28H19N5O5S2 [M+Na]+ 592.0725, found 591.9575.
δ 185.6, 150.0, 145.6, 145.0, 144.7, 143.8, 138.1, 137.4, 135.2, 133.6, 133.5, 133.1, 132.2, 131,9, 143.9, 139.1, 138.2, 137.5, 136.0, 135.5, 133.6, 133.2, 132.1, 132,0, 132.0, 131.5, 131.5, 131.1, 131.0, 130.6, 130.1, 128.7, 126.1, 125.6, 125.4, 125.1, 125.1, 20.1; HRMS (EI) calcd. for C28H19N5O5S [M+Na]+ 560.1004, found 560.1021.
4-isopropyl-2-(2-nitrophenyl)-2,4-dihydrothiochromeno[3,4-d][1,2,3]tri azole (4m)
light yellow solid with melting point of 225-228
oC; 1H NMR (400 MHz, CDCl3) δ 8.20 (d, J = 127.9, 127.1, 126.8, 126.3, 124.1, 44.9, 35.1, 24.3, 22.7, 21.1; HRMS (EI) calcd. for C29H18 N4O2S [M+Na]+ 389.1048, found 389.1058.
.
[M+H]+ 524.1024, found 524.1029.
(2-fluoro-2-methoxyphenyl)(2-(4-nitrophenyl)-5-(2-((4-nitrophenyl)thio )phenyl)-2H-1,2,3-triazol-4-yl)methanone (4p)
yellow solid with melting point of 147-149 oC;
1H NMR (400 MHz, CDCl3) δ 8.33 (d, J = 9.2
(4-fluoro-2-methoxyphenyl)(2-(4-nitrophenyl)-5-(2-((4-nitrophenyl)thio 131.3, 130.8, 130.4, 127.1, 125.5, 124.0, 119.8, 116.0 (d, JC-F = 21.8 Hz); HRMS (EI) calcd. 147.3, 147.3, 145.6, 145.5, 143.1, 140.8, 136.5, 134.4, 134.3, 131.9, 1319, 131.3, 130.7, 130.4, 129.1, 127.0, 125.5, 124.0, 119.9; HRMS (EI) calcd. for C28H18ClN5O6S [M+H]+ 558.0633, found 558.0626.
(2-methoxyphenyl)(2-(4-nitrophenyl)-5-(2-((4-nitrophenyl)thio)phenyl) -2H-1,2,3-triazol-4-yl)methanone (4s)
orange solid with melting point of 189-190 oC;
1H NMR (400 MHz, CDCl3) δ 8.29 (d, J = 9.2 146.9, 145.3, 143.1, 136.2, 134.3, 134.0, 131.8, 131.2, 130.9, 130.6, 129.9, 127.2, 127.0, 125.2, 123.8, 120.4, 119.5, 111.6, 55.7; HRMS (EI) calcd. for C28H19N5O6S [M+H]+ 542.0938, found 542.0934.
(3-methoxyphenyl)(2-(4-nitrophenyl)-5-(2-((4-nitrophenyl)thio)phenyl) -2H-1,2,3-triazol-4-yl)methanone (4t)
yellow solid with melting point of 187-189 oC;
1H NMR (400 MHz, CDCl3) δ 8.38 (d, J = 9.1 145.9, 145.6, 143.3, 137.3, 136.6, 134.5, 132.1, 131.2, 130.7, 130.4, 129.7, 126.9, 125.5, 124.0, 123.5, 120.4, 119.8, 114.7, 55.7; HRMS (EI) calcd. for C28H19N5O6S [M+H]+ 553.1050, found 553.1061.
(4-methoxyphenyl)(2-(4-nitrophenyl)-5-(2-((4-nitrophenyl)thio)phenyl)
orange solid with melting point of 199-200 oC;
1H NMR (400 MHz, CDCl3) δ 8.02 (dd, J = 8.2, 133.8, 133.3, 132.0, 130.5, 130.2, 128.6, 128.5, 126.6 (d, JC-F = 3.6 Hz), 126.0, 125.7, 125.3 (d, JC-F = 6.0 Hz), 119.8 (d, JC-F =23 Hz), 118.6 (d, JC-F = 21.5 Hz); HRMS (EI) calcd. for C27H16FN5O5S [M+Na]+ 564.0748, found 564.0752.
(5-(5-fluoro-2-((4-nitrophenyl)thio)phenyl)-2-(4-nitrophenyl)-2H-1,2,3-triazol-4-yl)(phenyl)methanone (4w)
yellow solid with melting point of 194-195
oC; 1H NMR (400 MHz, CDCl3) δ 8.39 (d,
(5-(5-methoxy-2-((4-nitrophenyl)thio)phenyl)-2-(4-nitrophenyl)-2H-1,2, 3-triazol-4-yl)(phenyl)methanone (4y)
orange solid with melting point of 199-200 oC; 1H NMR (400 MHz, CDCl3) δ 8.37 (d, J = 9.2 Hz, 2H), 8.25 (d, J = 9.2 Hz, 2H), 8.02 (d, J = 7.3 Hz, 2H), 7.84 (d, J = 8.8 Hz, 2H), 7.64-7.59 (m, 2H), 7.45 (t, J = 7.9 Hz, 2H), 7.31 (d, J
= 2.8 Hz, 1H), 7.12 (dd, J = 8.6, 2.8 Hz, 1H), 6.88 (d, J = 9.0 Hz, 2H), 3.94 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 185.9, 161.4, 150.6, 148.6, 147.3, 145.9, 145.2, 143.2, 138.8, 136.4, 136.0, 134.1, 130.5, 128.6, 125.8, 125.5, 123.9, 120.1, 119.7, 117.5, 117.2, 55.9; HRMS (EI) calcd. for C28H19O5N6S1 [M+H]+ 554.1128, found 554.1125.
2-6-2、X-ray
Single –Crystal X-ray Diffraction of 2a
Table 1. Crystal data and structure refinement for a16011.
Identification code a16011
Empirical formula C15 H11 N3 S Formula weight 265.33
Temperature 200(2) K Wavelength 0.71073 Å Crystal system Monoclinic Space group P 21/c
Density (calculated) 1.428 Mg/m3 Absorption coefficient 0.250 mm-1
F(000) 552
Crystal size 0.36 x 0.15 x 0.04 mm3 Theta range for data collection 2.48 to 25.04°.
Index ranges -9<=h<=9, -19<=k<=17, -11<=l<=7 Reflections collected 6615
Independent reflections 2173 [R(int) = 0.0745]
Completeness to theta = 25.04° 99.4 % Absorption correction multi-scan
Max. and min. transmission 0.9901 and 0.9155
Refinement method Full-matrix least-squares on F2 Data / restraints / parameters 2173 / 0 / 172
Goodness-of-fit on F2 1.050
Final R indices [I>2sigma(I)] R1 = 0.0559, wR2 = 0.1312 R indices (all data) R1 = 0.1044, wR2 = 0.1661 Largest diff. peak and hole 0.442 and -0.461 e.Å -3
Table 2. Atomic coordinates ( x 104) and equivalent isotropic
displacement parameters (Å 2x 103) for a16011. U(eq) is defined as one third of the trace of the orthogonalized Uij tensor.
____________________________________________________________
Table 3. Bond lengths [Å ] and angles [°] for a16011.
C(6)-C(1)-S(1) 122.8(3)
C(12)-C(13)-H(13) 120.0 C(14)-C(13)-H(13) 120.0 C(15)-C(14)-C(13) 119.7(3) C(15)-C(14)-H(14) 120.1 C(13)-C(14)-H(14) 120.1 C(14)-C(15)-C(10) 121.2(4) C(14)-C(15)-H(15) 119.4 C(10)-C(15)-H(15) 119.4 N(2)-N(1)-C(7) 111.8(2) N(2)-N(1)-H(1') 116.1 C(7)-N(1)-H(1') 131.3 N(3)-N(2)-N(1) 106.4(3) N(2)-N(3)-C(8) 108.7(2) C(1)-S(1)-C(9) 102.54(15)
____________________________________________________________
Symmetry transformations used to generate equivalent atoms:
Table 4. Anisotropic displacement parameters (Å 2x 103)for a16011.
The anisotropic displacement factor exponent takes the form:
- 2[ h2a*2U11 + ... + 2 h k a* b* U12 ]
Table 5. Hydrogen coordinates ( x 104) and isotropic displacement parameters (Å 2x 103) for a16011.
____________________________________________________________
x y z U(eq)
____________________________________________________________
H(2) 7731 -1185 3337 35
H(3) 8683 -1346 5714 38
H(4) 8413 -254 7273 38
H(5) 7178 987 6451 34
H(9) 5425 1263 394 22
H(11) 8734 2127 2551 33
H(12) 11379 2397 1970 41
H(13) 12198 1815 -15 47
H(14) 10375 936 -1436 52
H(15) 7738 657 -863 42
H(1') 4989 2119 5371 29
____________________________________________________________
Single –Crystal X-ray Diffraction of 3a
Table 1. Crystal data and structure refinement for 14910.
Identification code 14910
Empirical formula C21 H14 N4 O2 S Formula weight 386.42
Temperature 200(2) K Wavelength 0.71073 Å Crystal system Monoclinic
Space group P 2/c
Density (calculated) 1.258 Mg/m3 Absorption coefficient 0.182 mm-1
F(000) 1600
Crystal size 0.27 x 0.17 x 0.11 mm3 Theta range for data collection 0.89 to 25.06°.
Index ranges -28<=h<=25, -9<=k<=9, -23<=l<=26 Reflections collected 22670
Independent reflections 7221 [R(int) = 0.0635]
Completeness to theta = 25.06° 99.7 % Absorption correction multi-scan
Max. and min. transmission 0.9803 and 0.9526
Refinement method Full-matrix least-squares on F2 Data / restraints / parameters 7221 / 0 / 505
Goodness-of-fit on F2 0.950
Final R indices [I>2sigma(I)] R1 = 0.0555, wR2 = 0.1335 R indices (all data) R1 = 0.0931, wR2 = 0.1482 Largest diff. peak and hole 0.326 and -0.401 e.Å -3
Table 2. Atomic coordinates ( x 104) and equivalent isotropic
displacement parameters (Å 2x 103) for 14910. U(eq) is defined as one third of the trace of the orthogonalized Uij tensor.
____________________________________________________________
C(30) 1488(1) 11815(4) 4141(1) 30(1)
Table 3. Bond lengths [Å ] and angles [°] for 14910.
C(18)-H(18) 0.9500
C(37)-C(42) 1.393(4)
N(1)-C(7)-C(6) 124.5(2)
C(20)-C(19)-C(18) 120.2(3)
C(30)-C(31)-H(31) 120.4
N(1)-N(2)-N(3) 116.0(2) N(1)-N(2)-C(8) 122.6(2) N(3)-N(2)-C(8) 121.2(2) C(14)-N(3)-N(2) 102.4(2) O(1)-N(4)-O(2) 124.3(3) O(1)-N(4)-C(9) 117.9(3) O(2)-N(4)-C(9) 117.7(3) N(6)-N(5)-C(28) 103.2(2) N(5)-N(6)-N(7) 115.7(2) N(5)-N(6)-C(29) 123.4(2) N(7)-N(6)-C(29) 120.8(2) C(35)-N(7)-N(6) 102.2(2) O(3)-N(8)-O(4) 124.6(3) O(3)-N(8)-C(30) 117.8(3) O(4)-N(8)-C(30) 117.7(3) C(1)-S(1)-C(15) 104.03(14) C(22)-S(2)-C(36) 104.50(14)
____________________________________________________________
Symmetry transformations used to generate equivalent atoms:
Table 4. Anisotropic displacement parameters (Å 2x 103)for 14910.
The anisotropic displacement factor exponent takes the form:
- 2[ h2a*2U11 + ... + 2 h k a* b* U12 ]
C(30) 27(2) 26(2) 40(2) -3(1) 14(2) 2(1)
Table 5. Hydrogen coordinates ( x 104) and isotropic displacement parameters (Å 2x 103) for 14910.
____________________________________________________________
Single –Crystal X-ray Diffraction of 4a
Table 1. Crystal data and structure refinement for a14534.
Identification code a14534
Empirical formula C27 H17 N5 O5 S Formula weight 523.52
Temperature 200(2) K Wavelength 0.71073 Å Crystal system Triclinic
Space group P -1
Density (calculated) 1.483 Mg/m3 Absorption coefficient 0.190 mm-1
F(000) 540
Crystal size 0.44 x 0.32 x 0.13 mm3 Theta range for data collection 1.87 to 25.10°.
Index ranges -11<=h<=11, -13<=k<=10, -10<=l<=13
Reflections collected 10097
Independent reflections 4143 [R(int) = 0.0312]
Completeness to theta = 25.10° 98.9 % Absorption correction multi-scan
Max. and min. transmission 0.9757 and 0.9211
Refinement method Full-matrix least-squares on F2 Data / restraints / parameters 4143 / 0 / 343
Goodness-of-fit on F2 1.053
Final R indices [I>2sigma(I)] R1 = 0.0431, wR2 = 0.1230 R indices (all data) R1 = 0.0548, wR2 = 0.1428
Table 2. Atomic coordinates ( x 104) and equivalent isotropic
displacement parameters (Å 2x 103) for a14534. U(eq) is defined as one third of the trace of the orthogonalized Uij tensor.
____________________________________________________________
N(3) 9231(2) 7265(2) 8363(2) 28(1) N(4) 9085(2) 8427(2) 8312(2) 28(1) N(5) 9832(3) 7726(2) 6078(2) 39(1) O(1) 5356(2) 4571(2) 6858(2) 40(1) O(2) 6651(2) 5292(2) 5866(2) 49(1) O(3) 7539(2) 10472(2) 10357(2) 53(1) O(4) 8545(2) 7669(2) 5682(2) 49(1) O(5) 10665(3) 8495(2) 5986(2) 69(1) S(1) 5427(1) 6076(1) 9217(1) 33(1)
____________________________________________________________
Table 3. Bond lengths [Å ] and angles [°] for a14534.
C(19)-C(20) 1.368(4)
C(6)-C(5)-H(5) 119.2
C(19)-C(18)-H(18) 120.2
O(5)-N(5)-C(27) 117.5(2) O(4)-N(5)-C(27) 117.2(2) C(6)-S(1)-C(7) 101.00(10)
____________________________________________________________
Symmetry transformations used to generate equivalent atoms:
Table 4. Anisotropic displacement parameters (Å 2x 103)for a14534.
The anisotropic displacement factor exponent takes the form:
- 2[ h2a*2U11 + ... + 2 h k a* b* U12 ]
N(3) 32(1) 29(1) 30(1) 11(1) 15(1) 8(1) N(4) 31(1) 29(1) 28(1) 10(1) 13(1) 5(1) N(5) 54(2) 38(1) 32(1) 9(1) 20(1) 6(1) O(1) 56(1) 33(1) 34(1) 10(1) 17(1) 2(1) O(2) 57(1) 53(1) 47(1) 9(1) 33(1) 10(1) O(3) 80(2) 44(1) 54(1) 19(1) 44(1) 28(1) O(4) 56(1) 51(1) 36(1) 12(1) 6(1) 16(1) O(5) 85(2) 53(1) 93(2) 35(1) 50(1) 2(1) S(1) 43(1) 32(1) 25(1) 9(1) 11(1) -1(1)
____________________________________________________________
Table 5. Hydrogen coordinates ( x 104) and isotropic displacement parameters (Å 2x 103) for a14534.
____________________________________________________________
x y z U(eq)
____________________________________________________________
H(2) 5429 7125 5343 46
H(3) 4651 9054 5923 56
H(4) 4182 9708 7883 54
H(5) 4505 8450 9252 44
H(8) 4923 6718 11586 37
H(9) 6142 7914 13568 41
H(10) 8197 9135 13822 42
H(11) 9012 9188 12076 39
H(17) 7868 12452 9881 44
H(18) 7882 13836 8642 57
H(19) 7942 13114 6555 62
H(20) 7987 11037 5709 58
H(21) 7998 9644 6945 47
H(23) 10267 5264 8768 43
H(24) 11692 4026 7751 49
H(25) 12420 4552 6137 49
H(26) 11622 6253 5448 47