Page 218 - 《精细化工》2022年第7期

·1504· 精细化工 FINE CHEMICALS 第 39 卷

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8.35 (m, 2H, Ar—H), 7.88~7.82 (m, 1H, Ar—H), 7.71 体，产率为 45%。HNMR (400 MHz, CDCl 3 ), δ: 8.37~
(d, J = 8.0 Hz, 2H, Ar—H), 7.51~7.42 (m, 2H, Ar— 8.29 (m, 1H, Ar—H), 7.85~7.75 (m, 1H, Ar—H), 7.66
H), 5.24 (d, J = 5.2 Hz, 1H, CH), 3.65~3.55 (q, J = (d, J = 5.1 Hz, 1H, Ar—H), 7.46~7.39 (m, 2H, Ar—H),
6.8、7.0 Hz, 2H, CH 2 ), 3.45 (p, J = 7.0、6.7 Hz, 2H,
7.20 (d, J = 5.1 Hz, 1H, Ar—H), 4.82 (d, J = 5.0 Hz,
CH 2 ), 2.89 (dd, J = 14.2、7.5 Hz, 1H, CH 2), 2.54 (d, J = 1H, CH), 3.79~3.61 (q, J = 6.8、7.0 Hz, 2H, CH 2 ),
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14.1 Hz, 1H, CH 2 ), 1.76 (s, 3H, CH 3 )。 CNMR (100 3.58~3.45 (p, J = 7.0、6.5 Hz, 2H, CH 2 ), 2.85 (d, J =
MHz, CDCl 3 ), δ: 171.64, 150.57, 142.05, 139.26, 133.74,
131.91, 127.89, 127.59, 125.57, 125.11, 124.11, 123.16, 14.1 Hz, 1H, CH 2 ), 2.58 (d, J = 14.1 Hz, 1H, CH 2 ),
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120.06, 114.80, 103.60, 65.64, 49.21, 41.14, 30.37。 1.74 (s, 3H, CH 3 )。 CNMR (100 MHz, CDCl 3 ), δ:
172.72, 146.48, 144.59, 137.16, 131.80, 128.21, 125.09,
5-[(1,3-二氧戊基-2-基)甲基]-3-腈基-5-甲基苯
124.37, 124.11, 120.20, 120.09, 114.88, 103.61, 65.64,
并[4,5]咪唑[2,1-a]异喹啉-6(5H)-酮(Ⅲf)：无色液体， 49.59, 45.27, 30.76。
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产率为 62%。HNMR (400 MHz, CDCl 3), δ: 8.67 (d, J = 7-[(1,3-二氧戊基-2-基)甲基]-7-甲基苯并[f]苯并
8.0 Hz, 1H, Ar—H), 8.43~8.36 (m, 1H, Ar—H), 7.95~
[4,5]咪唑[2,1-a]异喹啉-8(7H)-酮(Ⅲj)：无色液体，
7.73 (m, 3H, Ar—H), 7.57~7.48 (m, 2H, Ar—H), 5.27
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产率为 50%。HNMR (400 MHz, CDCl 3), δ: 8.77 (d, J =
(d, J = 5.1 Hz, 1H, CH), 3.87~3.75 (q, J = 6.8、7.1 Hz,
8.5 Hz, 1H, Ar—H), 8.55 (d, J = 8.4 Hz, 1H, Ar—H),
2H, CH 2 ), 3.70 (p, J = 7.0、6.8 Hz, 2H, CH 2 ), 2.93 (d,
J =7.5 Hz, 1H, CH 2 ), 2.54 (d, J = 14.1 Hz, 1H, CH 2 ), 8.43 (d, J = 6.7 Hz, 1H, Ar—H), 8.19~7.82 (m, 4H,
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1.69 (s, 3H, CH 3 )。 CNMR (100 MHz, CDCl 3 ), δ: Ar—H), 7.70~7.53 (m, 3H, Ar—H), 4.86 (d, J = 5.0 Hz,
170.90, 147.01, 142.05, 141.00, 134.68, 131.99, 127.65, 1H, CH), 3.76~3.62 (q, J = 6.8、7.0 Hz, 2H, CH 2 ),
127.42, 127.20, 125.11, 124.11, 120.06, 118.09, 114.80, 3.58~3.41 (p, J = 7.0、6.5 Hz, 2H, CH 2 ), 2.82 (d, J =
113.86, 103.60, 65.64, 49.41, 41.17, 30.36。 14.1 Hz, 1H, CH 2 ), 2.61 (d, J = 14.1 Hz, 1H, CH 2 ),
5-[(1,3-二氧戊基-2-基)甲基]-1-甲氧基-5-甲基
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1.76 (s, 3H, CH 3 )。 CNMR (100 MHz, CDCl 3 ), δ:
苯并[4,5]咪唑[2,1-a]异喹啉-6(5H)-酮(Ⅲg)：无色液 173.34, 149.89, 142.07, 137.93, 134.75, 134.14, 132.03,
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体，产率为 50%。HNMR (400 MHz, CDCl 3 ), δ: 8.42~ 128.97, 128.78, 127.41, 127.28, 126.31, 125.90, 125.11,
8.34 (m, 1H, Ar—H), 7.95~7.89 (m, 1H, Ar—H), 7.55 124.11, 121.72, 120.06, 114.82, 103.76, 65.64, 49.16,
(t, J = 8.2 Hz, 1H, Ar—H), 7.49~7.39 (m, 2H, Ar—H), 41.64, 30.24。
7.20 (d, J = 8.0 Hz, 1H, Ar—H), 7.12 (d, J = 8.4 Hz, 5-[(1,3-二氧戊基-2-基)甲基]-5,9,10-三甲基苯
1H, Ar—H), 4.95 (d, J = 4.9 Hz, 1H, CH), 4.15 (s, 3H, 并[4,5]咪唑[2,1-a]异喹啉-6(5H)-酮(Ⅲk)：无色液体，
CH 3 ), 3.74~3.65 (q, J = 6.8、7.0 Hz, 2H, CH 2 ), 3.51 (p, 产率为 48%。HNMR (400 MHz, CDCl 3), δ: 8.53 (d, J =
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J = 7.0、6.5 Hz, 2H, CH 2 ), 2.86 (d, J = 14.1 Hz, 1H, 6.8 Hz, 1H, Ar—H), 8.15 (s, 1H, Ar—H), 7.68~7.48
CH 2 ), 2.52 (d, J = 14.1 Hz, 1H, CH 2 ), 1.71 (s, 3H,
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CH 3 )。 CNMR (100 MHz, CDCl 3 ), δ: 172.89, 159.28, (m, 3H, Ar—H), 4.83 (d, J = 5.0 Hz, 1H, CH), 3.76~
153.43, 141.69, 139.05, 131.85, 130.67, 125.09, 124.11, 3.62 (q, J = 6.8、7.0 Hz, 2H, CH 2 ), 3.53 (p, J = 7.0、
120.06, 119.80, 114.86, 112.59, 112.01, 103.60, 65.64, 6.5 Hz, 2H, CH 2 ), 2.83 (d, J = 14.1 Hz, 1H, CH 2 ), 2.50
56.25, 48.86, 41.53, 30.38。 (d, J = 14.1 Hz, 1H, CH 2 ), 2.45 (d, J = 6.9 Hz, 6H,
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5-[(1,3-二氧戊基-2-基)甲基]-1-溴-5-甲基苯并 2CH 3), 1.74 (s, 3H, CH 3 )。 CNMR (100 MHz, CDCl 3),
[4,5]咪唑[2,1-a]异喹啉-6(5H)-酮(Ⅲh)：无色液体， δ: 172.05, 148.64, 141.63, 136.41, 135.20, 134.11, 133.78,
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产率为 53%。HNMR (400 MHz, CDCl 3), δ: 8.55 (d, J = 131.37, 128.69, 127.41, 126.30, 126.07, 117.93, 115.68,
103.60, 65.64, 49.25, 41.21, 30.71, 20.01, 19.93。
7.1 Hz, 1H, Ar—H), 8.41~8.34 (m, 1H, Ar—H), 7.86~
7.82 (m, 1H, Ar—H), 7.66~7.53 (m, 2H, Ar—H), 7.46 2 结果与讨论
(tdd, J = 6.9、4.7、1.8 Hz, 2H, Ar—H), 4.87 (d, J =
5.0 Hz, 1H, CH), 3.64 (q, J = 6.8 Hz, 1H, CH 2 ), 3.55 2.1 反应条件优化
(q, J = 7.1 Hz, 1H, CH 2 ), 3.41 (p, J = 7.0、6.6 Hz, 2H,
以合成Ⅲa 为例，按照 1.2.2 节方法，以Ⅰa 和
CH 2 ), 2.92 (d, J = 14.2、7.5 Hz, 1H, CH 2 ), 2.52 (d, 1,3-二氧戊烷为原料，考察不同催化剂、氧化剂、溶
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J = 14.1 Hz, 1H, CH 2 ), 1.69 (s, 3H, CH 3 )。 CNMR
(100 MHz, CDCl 3 ), δ: 72.64, 149.87, 144.80, 137.96, 剂种类对Ⅲa 产率的影响，结果见表 1。
131.67, 131.35, 131.28, 125.23, 125.11, 124.74, 124.11,
123.95, 120.06, 114.80, 103.59, 65.64, 48.56, 41.14,
30.71。
4-[(1,3-二氧戊基-2-基)甲基]-4-甲基苯并[4,5]咪
唑[1,2-a]噻吩[2,3-c]吡啶-5(4H)-酮(Ⅲi)：红褐色液