Page 228 - 《精细化工》2023年第2期

·450· 精细化工 FINE CHEMICALS 第 40 卷

J = 8.2、5.3 Hz, 1H), 4.31 (d, J = 14.9 Hz, 1H), 4.04 (d, 2.6 Hz, 1H), 3.36 (q, J = 8.5 Hz, 1H), 1.85~1.96 (m,
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J = 14.9 Hz, 1H), 3.38 (td, J = 8.7、3.0 Hz, 1H), 3.30 3H), 1.73~1.64 (m, 1H)。 CNMR (126 MHz, CDCl 3 )，
(q, J = 8.5 Hz, 1H), 1.99 (dt, J = 9.9、5.0 Hz, 1H), δ：157.20, 143.37, 142.91, 127.84, 126.78, 126.10,
1.94~1.87 (m, 1H), 1.86~1.79 (m, 1H), 1.70~1.61 (m, 120.75, 116.10, 114.21, 111.30, 57.61, 55.45, 47.17,
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1H)。 CNMR (126 MHz, CDCl 3)，δ：149.17, 142.39, 31.96, 22.32。
127.94, 126.78, 124.93, 124.16, 123.79, 119.74, 4-(3,4-二甲氧基苯基)-1,2,3,3a,4,5-六氢吡咯并
1
115.15, 110.32, 75.68, 56.30, 46.05, 30.92, 21.23。 [1,2-a]喹唑啉（Ⅲaf）：黏稠液体，产率 44%。HNMR
4-(2-甲苯基)-1,2,3,3a,4,5-六氢吡咯并[1,2-a]喹 (500 MHz, CDCl 3 )，δ：7.13 (t, J = 7.6 Hz, 1H), 6.96 (d,
1
唑啉（Ⅲab）：黏稠液体，产率 79%。HNMR (500 MHz, J = 7.3 Hz, 1H), 6.83~6.72 (m, 3H), 6.64 (t, J = 7.3
CDCl 3 )，δ：7.25~7.20 (m, 1H), 7.15 (t, J = 7.8 Hz, 2H), Hz, 1H), 6.52 (d, J = 8.0 Hz, 1H), 4.59 (dd, J = 8.2、5.1
7.08 (t, J = 7.0 Hz, 2H), 6.94 (d, J = 7.3 Hz, 1H), 6.64 Hz, 1H), 4.37 (d, J = 14.8 Hz, 1H), 4.04 (d, J = 14.9 Hz,
(t, J = 7.3 Hz, 1H), 6.58 (d, J = 8.0 Hz, 1H), 4.73 (t, J 1H), 3.84 (d, J = 22.5 Hz, 6H), 3.51~3.45 (m, 1H),
= 6.7 Hz, 1H), 4.14 (s, 1H), 3.89 (d, J = 15.0 Hz, 1H), 3.40~3.33 (m, 1H), 2.02~1.86 (m, 3H), 1.76~ 1.67 (m,
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3.56 ~ 3.47 (m, 1H), 3.37 (q, J = 8.5 Hz, 1H), 2.33 (s, 1H)。 CNMR (126 MHz, CDCl 3 )，δ：149.02, 146.79,
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3H), 2.04~1.85 (m, 3H), 1.56~1.46 (m, 1H)。 CNMR 143.29, 127.89, 126.11, 120.64, 116.75, 116.10,
111.27, 111.15, 110.29, 57.75, 56.01, 55.87, 47.22,
(126 MHz, CDCl 3 )，δ：146.02, 143.84, 136.82, 130.63,
127.63, 126.73, 126.02, 125.14, 115.97, 111.83, 32.00, 22.37。
109.62, 76.43, 56.73, 47.61, 32.81, 22.61, 18.03。 4-(4-氟苯基)-1,2,3,3a,4,5-六氢吡咯并[1,2-a]喹
唑啉（Ⅲag）：白色固体，熔点 95.5~98.7 ℃（文献
4-(3-甲苯基)-1,2,3,3a,4,5-六氢吡咯并[1,2-a]喹
[5]
1
1
唑啉（Ⅲac）：黏稠液体，产率 74%。HNMR (500 MHz, 值 98.1~98.6 ℃ ），产率 84%。 HNMR (500 MHz,
CDCl 3 )，δ：7.14 (dd, J = 8.7、5.0 Hz, 3H), 7.02~6.93
CDCl 3 )，δ：7.19 (t, J = 7.7 Hz, 1H), 7.13 (t, J = 7.6 Hz,
(m, 3H), 6.65 (t, J = 7.4 Hz, 1H), 6.53 (d, J = 8.1 Hz,
1H), 6.98 (dd, J = 20.5、9.7 Hz, 4H), 6.64 (t, J = 7.3
1H), 4.59 (dd, J = 8.3、5.1 Hz, 1H), 4.37 (d, J = 14.9 Hz,
Hz, 1H), 6.53 (d, J = 8.0 Hz, 1H), 4.60 (dd, J = 8.3、 1H), 4.03 (d, J = 15.0 Hz, 1H), 3.50~3.31 (m, 2H), 2.02~
5.3 Hz, 1H), 4.34 (d, J = 14.8 Hz, 1H), 4.09 (d, J = 1.86 (m, 3H), 1.71~1.62 (m, 1H)。 CNMR (126 MHz,
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14.8 Hz, 1H), 3.46 (td, J = 8.7、2.9 Hz, 1H), 3.37 (q, J CDCl 3 )，δ：160.26 (d, J C—F =245.7 Hz), 146.04, 143.38,
= 8.5 Hz, 1H), 2.33 (s, 3H), 2.09~2.03 (m, 1H), 127.92, 127.17 (d, J C—F =7.56 Hz), 126.05, 120.53,
2.01~1.95 (m, 1H), 1.94~1.87 (m, 1H), 1.77~1.68 (m, 116.23, 115.69 (d, J C—F =22.68 Hz), 111.36, 77.03,
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1H)。 CNMR (126 MHz, CDCl 3 )，δ：150.40, 143.45, 57.53, 47.09, 31.83, 22.27。
138.79, 128.84, 127.84, 126.03, 125.95, 125.67,
121.97, 120.96, 116.17, 111.40, 76.77, 57.55, 47.21, 4-(4-氯苯基)-1,2,3,3a,4,5-六氢吡咯并[1,2-a]喹
32.18, 22.37, 21.58。 唑啉（Ⅲah）：白色固体，熔点 96.4~98.3 ℃（文献
[5]
1
值 99.0~99.5 ℃ ），产率 67%。 HNMR (500 MHz,
4-(4-甲苯基)-1,2,3,3a,4,5-六氢吡咯并[1,2-a]喹
1
唑啉（Ⅲad）：黏稠液体，产率 84%。HNMR (500 MHz, CDCl 3 ) ，δ：7.29~7.23 (m, 2H), 7.14 (t, J = 7.7 Hz,
1H), 7.08 (d, J = 8.7 Hz, 2H), 6.96 (d, J = 7.3 Hz, 1H),
CDCl 3)，δ：7.15~7.05 (m, 5H), 6.95 (d, J = 7.3 Hz, 1H), 6.66 (t, J = 7.4 Hz, 1H), 6.53 (d, J = 8.1 Hz, 1H), 4.61
6.66~6.61 (m, 1H), 6.52 (d, J = 8.0 Hz, 1H), 4.60 (dd, (dd, J = 8.3、5.3 Hz, 1H), 4.37 (d, J = 15.0 Hz, 1H),
J = 8.3、5.2 Hz, 1H), 4.35 (d, J = 14.7 Hz, 1H), 4.06 (d,
4.07 (d, J = 15.2 Hz, 1H), 3.47~3.33 (m, 2H), 2.08~
J = 14.9 Hz, 1H), 3.46 (td, J = 8.7、2.8 Hz, 1H), 3.37 1.87 (m, 3H), 1.65~1.73 (m, 1H)。 CNMR (126 MHz,
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(q, J = 8.6 Hz, 1H), 2.32 (s, 3H), 2.05~1.94 (m, 2H), CDCl 3 )，δ：148.70, 143.45, 130.08, 129.07, 127.96,
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1.93~1.86 (m, 1H), 1.76~1.67 (m, 1H)。 CNMR (126
126.60, 125.99, 120.46, 116.37, 111.42, 76.62, 57.19,
MHz, CDCl 3 )，δ：147.70, 143.44, 134.63, 129.66, 47.02, 31.77, 22.24。
127.82, 126.04, 125.27, 120.85, 116.09, 111.30, 57.61, 4-(4-溴苯基)-1,2,3,3a,4,5-六氢吡咯并[1,2-a]喹
47.14, 32.08, 22.34, 20.96。
唑啉（Ⅲai）：白色固体，熔点 96.8~99.2 ℃（文献
4-(4- 甲氧基苯基 )-1,2,3,3a,4,5- 六氢吡咯并 [5] 1
值 97.6~99.1 ℃ ），产率 52%。 HNMR (500 MHz,
[1,2-a]喹唑啉（Ⅲae）：白色固体，熔点 73.0~75.4 ℃ CDCl 3) ，δ：7.40 (d, J = 8.7 Hz, 2H), 7.14 (t, J = 7.6 Hz,
1
（文献值 73.7~75.3 ℃ [5] ），产率 50%。 HNMR 1H), 7.02 (d, J = 8.7 Hz, 2H), 6.96 (d, J = 7.4 Hz, 1H),
(500 MHz, CDCl 3 ) ，δ：7.13 (dd, J = 7.5、5.4 Hz, 3H), 6.66 (t, J = 7.3 Hz, 1H), 6.53 (d, J = 8.0 Hz, 1H), 4.61
6.95 (d, J = 7.3 Hz, 1H), 6.85 (d, J = 8.9 Hz, 2H), 6.64 (dd, J = 8.3、5.3 Hz, 1H), 4.37 (d, J = 15.0 Hz, 1H),
(t, J = 7.5 Hz, 1H), 6.52 (d, J = 7.7 Hz, 1H), 4.58 (dd, 4.07 (d, J = 15.4 Hz, 1H), 3.44 (td, J = 8.7、3.0 Hz,
J = 8.2、5.0 Hz, 1H), 4.37 (d, J = 14.9 Hz, 1H), 4.01 (d, 1H), 3.35 (q, J = 8.4 Hz, 1H), 2.08~1.88 (m, 3H),
J = 14.9 Hz, 1H), 3.79 (s, 3H), 3.46 (td, J = 8.7、 1.74~1.64 (m, 1H)。 CNMR (126 MHz, CDCl 3 )，δ：
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