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微波辐射下水合茚三酮与芳胺参与异色烯并[4,3-b]吲哚衍生物的合成(2)

时间:2021-07-20 20:34来源:毕业论文
在10 mL微波合成仪专用反应容器中依次加入水合茚三酮(1 mmol)、芳胺(1 mmol)以及2.0 mL的溶剂甲酸,充分混合后密封,在微波合成仪中自动预搅拌30-60 s后,1

在10 mL微波合成仪专用反应容器中依次加入水合茚三酮(1 mmol)、芳胺(1 mmol)以及2.0 mL的溶剂甲酸,充分混合后密封,在微波合成仪中自动预搅拌30-60 s后,100 ℃下反应20 min。并用薄层硅胶板(TCL)检测,反应结束后加入蒸馏水,离心,取固体重结晶即可得产物,烘干称量并计算产率。

2.4 实验数据

Benzo[e]isochromeno[4,3-b]indol-5(13H)-one (3a)

Yield: 0.242 g (85%); Mp: >300 oC; IR(KBr): 3458, 2954, 1677, 1564, 1450, 1378 cm-1. 1H NMR (400 MHz, DMSO-d6) δ= 12.451 (s, 1H, NH), 8.551 (d, J = 8.0 Hz, 1H, Ar-H), 8.302 (d, J = 8.0 Hz, 1H, Ar-H), 8.091 (d, J = 8.0 Hz, 1H, Ar-H), 8.020-7.95 5(m, 2H, Ar-H), 7.771 (d, J = 9.2 Hz, 1H, Ar-H), 7.714-7.675 (m, 2H, Ar-H), 7.601 (t, J = 7.6 Hz, 1H, Ar-H), 7.501(t, J = 7.6 Hz, 1H, Ar-H). 13C NMR (100 MHz, DMSO-d6) δ= 162.1, 136.5, 136.0, 132.6, 131.4, 131.1, 129.3, 129.1, 127.4, 127.2, 126.8, 125.9, 124.4, 123.8, 120.8, 118.4, 116.0, 114.3, 109.5. HRMS (ESI): m/z calcd for: C19H10NO2, 284.0712 [M-H]-; found: 284.0721.

Isochromeno[4,3-b]naphtho[2,3-e]indol-15(5H)-one (3b)

Yield: 0.238 g (71%); Mp: >300 oC; IR(KBr): 3392, 2934, 1667, 1574, 1455, 1371 cm-1. 1H NMR (400 MHz, DMSO-d6) δ= 12.451 (s, 1H, NH), 8.551 (d, J = 8.0 Hz, 1H, Ar-H), 8.302 (d, J = 8.0 Hz, 1H, Ar-H), 8.091 (d, J = 8.0 Hz, 1H, Ar-H), 8.020-7.95 5(m, 2H, Ar-H), 7.771 (d, J = 9.2 Hz, 1H, Ar-H), 7.714-7.675 (m, 2H, Ar-H), 7.601 (t, J = 7.6 Hz, 1H, Ar-H), 7.501(t, J = 7.6 Hz, 1H, Ar-H). 13C NMR (100 MHz, DMSO-d6) δ= 162.1, 136.5, 136.0, 132.6, 131.4, 131.1, 129.3, 129.1, 127.4, 127.2, 126.8, 125.9, 124.4, 123.8, 120.8, 118.4, 116.0, 114.3, 109.5. HRMS (ESI): m/z calcd for: C19H10NO2, 284.0712 [M-H]-; found: 284.0721.

Isochromeno[3',4':4,5]pyrrolo[3,2-f]quinolin-12(7H)-one (3c)来!自~751论-文|网www.751com.cn

Yield: 0.217 g (76%); Mp: >300 oC. IR(KBr): 3432, 2964, 1659, 1570, 1456, 1377 cm-1.1H NMR (400 MHz, DMSO-d6) δ= 12.711 (s, 1H, NH), 8.852 (d, J = 8.0 Hz, 2H, Ar-H), 8.312 (d, J = 7.6 Hz, 1H, Ar-H), 8.131 (t, J = 6.4 Hz, 1H, Ar-H), 8.020-7.941 (m, 2H, Ar-H), 7.862 (d, J = 9.2 Hz, 1H, Ar-H), 7.703-7.671 (m, 1H, Ar-H), 7.612 (t, J = 7.6 Hz, 1H, Ar-H). 13C NMR (100 MHz, DMSO-d6) δ= 163.5, 161.9, 148.0, 145.3, 136.1, 131.9, 131.7, 131.5, 130.9, 127.9, 126.6, 124.4, 122.1, 121.9, 121.0, 118.7, 117.8, 117.0. HRMS (ESI): m/z calcd for: C18H9N2O2, 285.0664 [M-H]-; found: 285.0644.

3H-isochromeno[4,3-b]pyrrolo[3,2-e]indol-11(6H)-one (3d)

Yield: 0.203 g (74%);Mp: >300 oC. IR(KBr): 3445, 2950, 1687, 1569, 1429, 1366 cm-1. 1H NMR (400 MHz, DMSO-d6) δ= 13.300 (s, 1H, NH), 12.291 (s, 1H, NH), 8.281 (t, J = 8.0 Hz, 2H, Ar-H), 8.072 (d, J = 8.0 Hz, 1H, Ar-H), 7.963 (t, J = 7.6 Hz, 1H, Ar-H), 7.561 (t, J = 7.2 Hz, 2H, Ar-H), 7.501 (d, J = 8.8 Hz, 1H, CH), 3.481-3.410 (m, 1H, CH). 13C NMR (100 MHz, DMSO-d6) δ= 162.1, 135.9, 134.7, 131.5, 131.1, 130.4, 127.4, 120.8, 118.7, 116.4, 113.5, 113.0, 108.8, 105.9, 56.5, 19.0. HRMS (ESI): m/z calcd for: C17H9N2O2, 273.0664 [M-H]-; found: 273.0656.

微波辐射下水合茚三酮与芳胺参与异色烯并[4,3-b]吲哚衍生物的合成(2):http://www.751com.cn/yixue/lunwen_78607.html
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