纳米TiO2催化一锅法合成喹唑啉酮并酞嗪酮及3-酰胺基异吲哚酮并喹唑啉酮类化合物

doi:10.7503/cjcu20160292

高等学校化学学报 ›› 2016, Vol. 37 ›› Issue (9): 1629.doi: 10.7503/cjcu20160292

纳米TiO₂催化一锅法合成喹唑啉酮并酞嗪酮及3-酰胺基异吲哚酮并喹唑啉酮类化合物

张金^1,², 刘佳¹, 马养民^1,²(), 杨秀芳^1,², 程佩¹, 范超¹, 卢萍¹

1. 陕西科技大学化学与化工学院, 西安 710021
2. 教育部轻化工助剂化学与技术重点实验室, 西安 710021

收稿日期:2016-04-29 出版日期:2016-09-10 发布日期:2016-08-18
作者简介:联系人简介: 马养民, 男, 博士, 教授, 博士生导师, 主要从事天然产物提取、鉴定及合成研究. E-mail:mym63@sina.com
基金资助:
陕西省自然科学基础研究计划项目(批准号: 2014JQ2064)、陕西省教育厅重点实验室项目(批准号: 15JS012)和陕西科技大学博士科研启动基金(批准号: BJ12-26)资助

TiO₂ Nanoparticles-catalyzed One-pot Synthesis of Quinazolino[2,1-b]phthalazin-8-one and 3-Acylamino Isoindolo[2,1-a]quinazoline Derivatives^†

ZHANG Jin^1,², LIU Jia¹, MA Yangmin^1,^2,^*(), YANG Xiufang^1,², CHENG Pei¹, FAN Chao¹, LU Ping¹

1. College of Chemistry & Chemical Engineering, Shaanxi University of Science & Technology, Xi’an 710021, China
2. Key Laboratory of Auxiliary Chemistry & Technology for Chemical Industry, Ministry of Education, Xi’an 710021, China

Received:2016-04-29 Online:2016-09-10 Published:2016-08-18
Contact: MA Yangmin E-mail:mym63@sina.com
Supported by:
† Supported by the Natural Science Basic Research Plan in Shaanxi Province of China(No.2014JQ2064), the Scientific Research Project Item for Key Laboratory of Shaanxi Province Education Department, China(No.15JS012) and the Foundation for Young Scholars of Shaanxi University of Science & Technology, China(No.BJ12-26)

摘要/Abstract

摘要：

以纳米TiO₂为催化剂, 靛红酸酐、 2-甲酰基苯甲酸、不同芳香肼或酰肼类化合物为原料, 在乙醇/水溶液为溶剂的条件下一锅法合成, 高产率得到6个喹唑啉酮并酞嗪酮类化合物及10个3-酰胺基取代的异吲哚酮并喹唑啉酮类化合物. 该方法简洁高效, 反应条件温和, 为喹唑啉酮并杂环类化合物的合成提供了一条新途径.

关键词: 纳米TiO2, 一锅法, 喹唑啉酮并酞嗪酮, 3-酰胺基异吲哚酮并喹唑啉酮

Abstract:

An efficient and simple one-pot method was developed for the synthesis of two kinds of N-fused quinazolinone derivatives using nano TiO₂ particles as catalyst from isatoic anhydride, 2-carboxy benzaldehyde, hydrazides or aromatic hydrazines. Six quinazolino[2,1-b]phthalazin-8-ones and ten 3-acylamino isoindolo[2,1-a]quinazolines were obtained in excellent yields, and the reaction refluxed in aqueous ethanol were environmentally friendly. Attractive features of this methodology were its versatility, mild condition and high efficiency in creating two different structures in a single operation.

Key words: TiO2 Nanoparticles, One-pot reaction, Quinazolino[2, 1-b]phthalazin-8-one, 3-Acylamino isoindolo[2, 1-a]quinazoline

TrendMD:

张金, 刘佳, 马养民, 杨秀芳, 程佩, 范超, 卢萍. 纳米TiO₂催化一锅法合成喹唑啉酮并酞嗪酮及3-酰胺基异吲哚酮并喹唑啉酮类化合物. 高等学校化学学报, 2016, 37(9): 1629.

ZHANG Jin, LIU Jia, MA Yangmin, YANG Xiufang, CHENG Pei, FAN Chao, LU Ping. TiO₂ Nanoparticles-catalyzed One-pot Synthesis of Quinazolino[2,1-b]phthalazin-8-one and 3-Acylamino Isoindolo[2,1-a]quinazoline Derivatives^†. Chem. J. Chinese Universities, 2016, 37(9): 1629.

图/表 7

Scheme 1 Synthesis of isoindolo[2,1-a]quinazolinone and quinazolino[2,1-b]phthalazine-5,8-dione derivatives

Table 1 Appearance, yields, melting points and HR-MS data of compounds 5a—5f and 6a—6j

Compd.	Appearance	m.p./℃	HRMS(ESI)(calcd.), m/z[M+H]⁺	IR(KBr), $ν ˙$ /cm^-1
5a	White solid	245—246	342.1232(342.1243)	3293.95, 1717.96, 1683.31, 1600.41, 1487.01, 1392.01, 1110.09,
				758.47, 732.64
5b	White solid	252—253	372.1341(372.1348)	3263.77, 2922.53, 1725.46, 1676.33, 1508.99, 1395.38, 1241.86,
				1034.45, 830.91, 759.64
5c	White solid	232—233	376.0849(376.0853)	3444.35, 1731.17, 1653.93, 1489.08, 1092.97, 758.68
5d	White solid	217—218	376.0839(376.0853)	3274.34, 1728.73, 1673.91, 1482.52, 1390.51, 832.60, 746.33
5e	White solid	244—245	406.0950(406.0958)	3337.28, 1727.03, 1672.30, 1489.39, 1170.36, 819.94, 746.97
5f	White solid	211—213	410.0454(410.0463)	3273.08, 1731.55, 1672.65, 1511.90, 1484.64, 1390.70, 1035.14,
				817.26, 743.78
6a	White solid	226—227	370.1192(370.1189)	3201.30, 1722.10, 1696.06, 1653.01, 1483.08, 1401.30, 1278.07,
				898.23, 742.77
6b	White solid	250—251	406.1166(406.1168)	3261.70, 1732.09, 1705.10, 1648.53, 1489.10, 1400.14, 1269.99,
				754.87
6c	White solid	248—249	400.1288(400.1297)	3251.24, 1713.09, 1646.11, 1605.37, 1489.62, 1399.55, 1260.85,
				844.67, 751.28
6d	White solid	221—223	371.1137(371.1144)	3253.69, 1735.64, 1701.98, 1651.96, 1488.34, 1399.09, 1272.24,
				909.02, 756.70
6e	White solid	241—242	308.1026(308.1035)	3293.50, 1729.82, 1703.97, 1662.84, 1605.80, 1489.33, 1398.79,
				756.30, 737.31
6f	White solid	234—235	404.0788(404.0802)	3268.57, 1732.19, 1701.19, 1650.34, 1483.76, 1395.90, 909.89,
				749.42
6g	White solid	214—216	418.0947(418.0958)	3278.24, 1718.74, 1657.16, 1486.11, 1398.10, 175.05, 832.03,
				746.18
Compd.	Appearance	m.p./℃	HRMS(ESI)(calcd.), m/z[M+H]⁺	IR(KBr), $ν ˙$ /cm^-1
6h	White solid	233—234	456.0723(456.0727)	1735.29, 1654.35, 1508.35, 1021.70, 669.81
6i	White solid	199—201	405.0748(405.0754)	3240.55, 1709.44, 1654.75, 1483.51, 1396.86, 1098.93, 913.88,
				744.85
6j	White solid	217—219	342.0636(342.0645)	3274.39, 1733.21, 1705.90, 1668.70, 1485.00, 1397.00, 825.31,
				745.87

Table 1 Appearance, yields, melting points and HR-MS data of compounds 5a—5f and 6a—6j

Compd.	Appearance	m.p./℃	HRMS(ESI)(calcd.), m/z[M+H]⁺	IR(KBr), $ν ˙$ /cm^-1
5a	White solid	245—246	342.1232(342.1243)	3293.95, 1717.96, 1683.31, 1600.41, 1487.01, 1392.01, 1110.09,
				758.47, 732.64
5b	White solid	252—253	372.1341(372.1348)	3263.77, 2922.53, 1725.46, 1676.33, 1508.99, 1395.38, 1241.86,
				1034.45, 830.91, 759.64
5c	White solid	232—233	376.0849(376.0853)	3444.35, 1731.17, 1653.93, 1489.08, 1092.97, 758.68
5d	White solid	217—218	376.0839(376.0853)	3274.34, 1728.73, 1673.91, 1482.52, 1390.51, 832.60, 746.33
5e	White solid	244—245	406.0950(406.0958)	3337.28, 1727.03, 1672.30, 1489.39, 1170.36, 819.94, 746.97
5f	White solid	211—213	410.0454(410.0463)	3273.08, 1731.55, 1672.65, 1511.90, 1484.64, 1390.70, 1035.14,
				817.26, 743.78
6a	White solid	226—227	370.1192(370.1189)	3201.30, 1722.10, 1696.06, 1653.01, 1483.08, 1401.30, 1278.07,
				898.23, 742.77
6b	White solid	250—251	406.1166(406.1168)	3261.70, 1732.09, 1705.10, 1648.53, 1489.10, 1400.14, 1269.99,
				754.87
6c	White solid	248—249	400.1288(400.1297)	3251.24, 1713.09, 1646.11, 1605.37, 1489.62, 1399.55, 1260.85,
				844.67, 751.28
6d	White solid	221—223	371.1137(371.1144)	3253.69, 1735.64, 1701.98, 1651.96, 1488.34, 1399.09, 1272.24,
				909.02, 756.70
6e	White solid	241—242	308.1026(308.1035)	3293.50, 1729.82, 1703.97, 1662.84, 1605.80, 1489.33, 1398.79,
				756.30, 737.31
6f	White solid	234—235	404.0788(404.0802)	3268.57, 1732.19, 1701.19, 1650.34, 1483.76, 1395.90, 909.89,
				749.42
6g	White solid	214—216	418.0947(418.0958)	3278.24, 1718.74, 1657.16, 1486.11, 1398.10, 175.05, 832.03,
				746.18
Compd.	Appearance	m.p./℃	HRMS(ESI)(calcd.), m/z[M+H]⁺	IR(KBr), $ν ˙$ /cm^-1
6h	White solid	233—234	456.0723(456.0727)	1735.29, 1654.35, 1508.35, 1021.70, 669.81
6i	White solid	199—201	405.0748(405.0754)	3240.55, 1709.44, 1654.75, 1483.51, 1396.86, 1098.93, 913.88,
				744.85
6j	White solid	217—219	342.0636(342.0645)	3274.39, 1733.21, 1705.90, 1668.70, 1485.00, 1397.00, 825.31,
				745.87

Table 2 1H NMR and 13C NMR data of compounds 5a—5f and 6a—6j

Compd.	¹H NMR(400 MHz), δ^a	¹³C NMR(100 MHz), δ^b
5a	8.27(d, J=7.9 Hz, 1H), 8.16(dd, J=7.8, 1.4 Hz, 1H), 8.02(d, J=7.6 Hz, 1H), 7.89(d, J=6.7 Hz, 1H), 7.76—7.69(m, 1H), 7.59(t, J=7.3 Hz, 1H), 7.50(d, J=6.8 Hz, 1H), 7.37(dd, J=12.5, 4.7 Hz, 1H), 7.26(d, J=8.3 Hz, 1H), 7.08—7.00(m, 2H), 6.84(s, 1H), 6.58(s, 2H), 6.37(s, 1H)	165.40, 154.72, 146.89, 133.95, 133.55, 131.48, 129.96, 128.73, 128.44, 126.23, 124.86, 123.93, 121.46, 121.08, 119.97, 118.94, 113.90, 113.54, 72.60
5b	8.27(d, J=8.1 Hz, 1H), 8.16(dd, J=7.8, 1.3 Hz, 1H), 8.02(d, J=7.5 Hz, 1H), 7.91(d, J=7.5 Hz, 1H), 7.75—7.66(m, 1H), 7.59(t, J=7.4 Hz, 1H), 7.52(t, J=7.4 Hz, 1H), 7.41—7.32(m, 1H), 6.63(d, J=6.4 Hz, 3H), 6.56(s, 2H), 6.37(s, 1H), 3.69(s, 3H)	165.89, 154.99, 138.81, 137.43, 134.36, 133.16, 131.98, 130.42, 129.17, 126.89, 125.32, 124.38, 121.46, 120.43, 115.99, 114.32, 112.90, 107.73, 73.05, 55.48
5c	8.27(d, J=8.1 Hz, 1H), 8.15(d, J=9.2 Hz, 1H), 8.03(d, J=7.6 Hz, 1H), 7.84(d, J=7.0 Hz, 1H), 7.77—7.69(m, 1H), 7.61(t, J=7.5 Hz, 1H), 7.52(dd, J=13.2, 6.2 Hz, 1H), 7.37(t, J=7.3 Hz, 1H), 7.02(d, J=2.9 Hz, 2H), 6.81(s, 1H), 6.52(d, J=6.5 Hz, 2H), 6.36(s, 1H)	166.32, 165.78, 146.09, 138.54, 137.51, 134.59, 133.27, 132.00, 130.59, 129.24, 128.94, 126.91, 126.53, 125.42, 124.56, 120.54, 118.37, 115.69, 73.08
5d	8.24(d, J=8.5 Hz, 1H), 8.11(d, J=2.1 Hz, 1H), 8.02(d, J=7.5 Hz, 1H), 7.89(s, 1H), 7.66(dd, J=8.7, 2.1 Hz, 1H), 7.60(t, J=7.2 Hz, 1H), 7.51(s, 1H), 7.08(t, J=25.5 Hz, 2H), 6.85(s, 2H), 6.57(s, 2H), 6.37(s, 1H)	165.29, 164.67, 138.01, 135.45, 135.42, 133.82, 132.87, 131.20, 130.53, 130.10, 128.49, 128.41, 126.34, 124.02, 121.63, 121.41, 113.94, 113.92, 72.58
5e	8.23(d, J=8.7 Hz, 1H), 8.11(d, J=2.4 Hz, 1H), 8.01(d, J=7.5 Hz, 1H), 7.90(d, J=7.4 Hz, 1H), 7.66(dd, J=8.7, 2.5 Hz, 1H), 7.60(t, J=7.4 Hz, 1H), 7.53(t, J=7.4 Hz, 1H), 6.63(dd, J=36.5, 30.4 Hz, 5H), 6.36(s, 1H), 3.69(s, 3H)	165.31, 154.60, 138.11, 133.76, 132.87, 131.18, 130.49, 130.08, 128.35, 126.45, 123.98, 121.38, 115.51, 113.85, 72.39, 54.98
5f	8.23(d, J=8.6 Hz, 1H), 8.10(d, J=2.4 Hz, 1H), 8.02(d, J=7.6 Hz, 1H), 7.84(d, J=6.4 Hz, 1H), 7.67(dd, J=8.7, 2.4 Hz, 1H), 7.61(t, J=7.4 Hz, 1H), 7.53(d, J=6.9 Hz, 1H), 7.01(d, J=6.3 Hz, 2H), 6.84(s, 1H), 6.50(d, J=5.4 Hz, 2H), 6.35(s, 1H)	165.23, 145.27, 137.81, 135.42, 133.99, 133.00, 131.16, 130.61, 130.25, 128.38, 126.52, 126.09, 124.15, 121.49, 115.12, 72.44
6a	11.18(s, 1H), 8.13—8.08(m, 1H), 8.08—8.01(m, 3H), 7.99(d, J=7.4 Hz, 1H), 7.85(s, 1H), 7.81(d, J=8.0 Hz, 1H), 7.76(d, J=7.2 Hz, 1H), 7.69(d, J=7.3 Hz, 1H), 7.61(t, J=7.6 Hz, 2H), 7.51(d, J=7.5 Hz, 1H), 7.46(t, J=7.6 Hz, 1H), 6.84(s, 1H)	166.34, 164.79, 163.41, 138.65, 136.79, 134.34, 133.45, 132.67, 131.52, 131.31, 130.71, 128.84, 127.71, 127.40, 125.56, 125.51, 124.20, 120.39, 118.98, 71.51
6b	8.33(s, 1H), 8.14(dd, J=7.6, 5.2 Hz, 2H), 8.01—7.96(m, 1H), 7.86(d, J=8.0 Hz, 2H), 7.73—7.68(m, 1H), 7.66—7.59(m, 2H), 7.56(d, J=6.2 Hz, 1H), 7.37(d, J=7.7 Hz, 1H), 7.32(d, J=7.8 Hz, 2H), 6.82(s, 1H), 2.47(s, 3H)	167.33, 164.92, 164.04, 143.35, 137.85, 136.61, 133.92, 132.35, 131.84, 130.05, 129.20, 129.12, 127.75, 127.12, 125.01, 124.96, 124.34, 120.18, 118.62, 71.61, 21.18
6c	11.02(s, 1H), 8.10(d, J=7.9 Hz, 1H), 8.05(d, J=7.7 Hz, 1H), 8.00(t, J=8.1 Hz, 3H), 7.84—7.78(m, 2H), 7.77—7.73(m, 1H), 7.47(d, J=7.3 Hz, 2H), 7.14(d, J=8.8 Hz, 2H), 6.82(s, 1H), 3.88(s, 3H)	164.77, 163.51, 162.64, 138.73, 136.79, 135.24, 134.28, 134.18, 133.39, 131.54, 130.67, 129.73, 128.85, 125.46, 124.16, 123.41, 120.34, 119.06, 114.07, 71.53, 55.51
6d	9.20(s, 1H), 8.91—8.75(m, 2H), 8.33(dt, J=7.9, 1.7 Hz, 1H), 8.12(t, J=7.6 Hz, 2H), 7.97(d, J=8.6 Hz, 1H), 7.71(t, J=7.7 Hz, 1H), 7.63(dd, J=5.5, 3.2 Hz, 2H), 7.50(d, J=7.9 Hz, 2H), 7.36(t, J=7.9 Hz, 1H), 6.79(s, 1H)	165.65, 164.92, 163.92, 152.94, 147.75, 137.54, 136.55, 135.40, 134.15, 132.48, 131.76, 130.26, 129.12, 126.75, 125.09, 124.71, 124.50, 123.50, 120.27, 118.35, 71.57
6e	10.52(s, 1H), 8.06(d, J=8.3 Hz, 1H), 8.01(d, J=7.5 Hz, 1H), 7.96(d, J=7.4 Hz, 1H), 7.82(d, J=8.3 Hz, 1H), 7.80—7.73(m, 2H), 7.67(d, J=7.3 Hz, 1H), 7.43(t, J=7.3 Hz, 1H), 6.66(s, 1H), 2.12(s, 3H)	169.64, 164.77, 163.19, 138.61, 136.72, 134.21, 133.37, 131.44, 130.66, 128.78, 125.97, 125.41, 124.07, 120.33, 118.97, 71.25, 20.45
Compd.	¹H NMR(400 MHz), δ^a	¹³C NMR(100 MHz), δ^b
6f	8.68(s, 1H), 8.06(d, J=8.7 Hz, 1H), 7.91(dd, J=8.0, 4.7 Hz, 4H), 7.60(dd, J=8.9, 5.5 Hz, 4H), 7.48(dd, J=16.5, 8.6 Hz, 3H), 6.70(s, 1H)	167.03, 164.66, 163.18, 137.41, 134.97, 133.97, 132.64, 132.58, 131.28, 130.58, 130.27, 130.22, 128.64, 128.54, 127.08, 124.93, 124.41, 121.63, 119.63, 71.37
6g	8.74(s, 1H), 8.04(d, J=8.7 Hz, 1H), 7.87(dd, J=5.1, 3.2 Hz, 2H), 7.80(d, J=8.2 Hz, 2H), 7.63—7.56(m, 3H), 7.48(dd, J=8.4, 3.6 Hz, 1H), 7.22(d, J=8.0 Hz, 2H), 6.65(s, 1H), 2.41(s, 3H)	167.35, 165.12, 163.71, 143.83, 137.90, 135.44, 134.39, 133.03, 131.70, 130.98, 130.63, 129.60, 129.09, 127.85, 127.59, 125.47, 124.82, 122.06, 120.11, 71.82, 21.65
6h	8.57(s, 1H), 8.08(d, J=8.7 Hz, 1H), 7.93(dd, J=14.0, 5.6 Hz, 4H), 7.64(tt, J=7.4, 4.1 Hz, 3H), 7.57—7.50(m, 1H), 6.95(d, J=8.8 Hz, 2H), 6.72(s, 1H), 3.90(s, 3H)	166.96, 165.17, 163.80, 163.45, 138.04, 135.51, 134.39, 133.02, 131.80, 131.03, 130.64, 129.63, 129.12, 125.53, 124.85, 122.94, 122.11, 120.25, 114.22, 71.93, 55.52
6i	11.43(s, 1H), 9.17(s, 1H), 8.88(d, J=4.0 Hz, 1H), 8.44—8.28(m, 1H), 8.14(dd, J=8.7, 2.9 Hz, 1H), 8.03—7.98(m, 2H), 7.91(dd, J=8.7, 2.6 Hz, 1H), 7.82(t, J=7.0 Hz, 1H), 7.76(t, J=7.3 Hz, 1H), 7.67(d, J=3.0 Hz, 1H), 7.59(d, J=7.4 Hz, 1H), 6.85(s, 1H)	165.14, 164.78, 162.24, 153.25, 148.63, 138.34, 135.68, 135.58, 134.26, 133.75, 131.19, 130.89, 129.62, 128.06, 125.78, 124.31, 123.99, 122.41, 120.46, 99.50, 71.46
6j	10.60(s, 1H), 8.06(d, J=8.7 Hz, 1H), 7.95(d, J=7.9 Hz, 2H), 7.83(t, J=7.5 Hz, 2H), 7.76(d, J=7.1 Hz, 1H), 7.64(d, J=7.5 Hz, 1H), 6.64(s, 1H), 2.11(s, 3H)	169.93, 164.86, 162.14, 138.25, 135.48, 134.07, 133.63, 131.04, 130.83, 129.59, 127.93, 125.93, 124.18, 122.34, 120.50, 71.18, 20.34

Table 2 1H NMR and 13C NMR data of compounds 5a—5f and 6a—6j

Compd.	¹H NMR(400 MHz), δ^a	¹³C NMR(100 MHz), δ^b
5a	8.27(d, J=7.9 Hz, 1H), 8.16(dd, J=7.8, 1.4 Hz, 1H), 8.02(d, J=7.6 Hz, 1H), 7.89(d, J=6.7 Hz, 1H), 7.76—7.69(m, 1H), 7.59(t, J=7.3 Hz, 1H), 7.50(d, J=6.8 Hz, 1H), 7.37(dd, J=12.5, 4.7 Hz, 1H), 7.26(d, J=8.3 Hz, 1H), 7.08—7.00(m, 2H), 6.84(s, 1H), 6.58(s, 2H), 6.37(s, 1H)	165.40, 154.72, 146.89, 133.95, 133.55, 131.48, 129.96, 128.73, 128.44, 126.23, 124.86, 123.93, 121.46, 121.08, 119.97, 118.94, 113.90, 113.54, 72.60
5b	8.27(d, J=8.1 Hz, 1H), 8.16(dd, J=7.8, 1.3 Hz, 1H), 8.02(d, J=7.5 Hz, 1H), 7.91(d, J=7.5 Hz, 1H), 7.75—7.66(m, 1H), 7.59(t, J=7.4 Hz, 1H), 7.52(t, J=7.4 Hz, 1H), 7.41—7.32(m, 1H), 6.63(d, J=6.4 Hz, 3H), 6.56(s, 2H), 6.37(s, 1H), 3.69(s, 3H)	165.89, 154.99, 138.81, 137.43, 134.36, 133.16, 131.98, 130.42, 129.17, 126.89, 125.32, 124.38, 121.46, 120.43, 115.99, 114.32, 112.90, 107.73, 73.05, 55.48
5c	8.27(d, J=8.1 Hz, 1H), 8.15(d, J=9.2 Hz, 1H), 8.03(d, J=7.6 Hz, 1H), 7.84(d, J=7.0 Hz, 1H), 7.77—7.69(m, 1H), 7.61(t, J=7.5 Hz, 1H), 7.52(dd, J=13.2, 6.2 Hz, 1H), 7.37(t, J=7.3 Hz, 1H), 7.02(d, J=2.9 Hz, 2H), 6.81(s, 1H), 6.52(d, J=6.5 Hz, 2H), 6.36(s, 1H)	166.32, 165.78, 146.09, 138.54, 137.51, 134.59, 133.27, 132.00, 130.59, 129.24, 128.94, 126.91, 126.53, 125.42, 124.56, 120.54, 118.37, 115.69, 73.08
5d	8.24(d, J=8.5 Hz, 1H), 8.11(d, J=2.1 Hz, 1H), 8.02(d, J=7.5 Hz, 1H), 7.89(s, 1H), 7.66(dd, J=8.7, 2.1 Hz, 1H), 7.60(t, J=7.2 Hz, 1H), 7.51(s, 1H), 7.08(t, J=25.5 Hz, 2H), 6.85(s, 2H), 6.57(s, 2H), 6.37(s, 1H)	165.29, 164.67, 138.01, 135.45, 135.42, 133.82, 132.87, 131.20, 130.53, 130.10, 128.49, 128.41, 126.34, 124.02, 121.63, 121.41, 113.94, 113.92, 72.58
5e	8.23(d, J=8.7 Hz, 1H), 8.11(d, J=2.4 Hz, 1H), 8.01(d, J=7.5 Hz, 1H), 7.90(d, J=7.4 Hz, 1H), 7.66(dd, J=8.7, 2.5 Hz, 1H), 7.60(t, J=7.4 Hz, 1H), 7.53(t, J=7.4 Hz, 1H), 6.63(dd, J=36.5, 30.4 Hz, 5H), 6.36(s, 1H), 3.69(s, 3H)	165.31, 154.60, 138.11, 133.76, 132.87, 131.18, 130.49, 130.08, 128.35, 126.45, 123.98, 121.38, 115.51, 113.85, 72.39, 54.98
5f	8.23(d, J=8.6 Hz, 1H), 8.10(d, J=2.4 Hz, 1H), 8.02(d, J=7.6 Hz, 1H), 7.84(d, J=6.4 Hz, 1H), 7.67(dd, J=8.7, 2.4 Hz, 1H), 7.61(t, J=7.4 Hz, 1H), 7.53(d, J=6.9 Hz, 1H), 7.01(d, J=6.3 Hz, 2H), 6.84(s, 1H), 6.50(d, J=5.4 Hz, 2H), 6.35(s, 1H)	165.23, 145.27, 137.81, 135.42, 133.99, 133.00, 131.16, 130.61, 130.25, 128.38, 126.52, 126.09, 124.15, 121.49, 115.12, 72.44
6a	11.18(s, 1H), 8.13—8.08(m, 1H), 8.08—8.01(m, 3H), 7.99(d, J=7.4 Hz, 1H), 7.85(s, 1H), 7.81(d, J=8.0 Hz, 1H), 7.76(d, J=7.2 Hz, 1H), 7.69(d, J=7.3 Hz, 1H), 7.61(t, J=7.6 Hz, 2H), 7.51(d, J=7.5 Hz, 1H), 7.46(t, J=7.6 Hz, 1H), 6.84(s, 1H)	166.34, 164.79, 163.41, 138.65, 136.79, 134.34, 133.45, 132.67, 131.52, 131.31, 130.71, 128.84, 127.71, 127.40, 125.56, 125.51, 124.20, 120.39, 118.98, 71.51
6b	8.33(s, 1H), 8.14(dd, J=7.6, 5.2 Hz, 2H), 8.01—7.96(m, 1H), 7.86(d, J=8.0 Hz, 2H), 7.73—7.68(m, 1H), 7.66—7.59(m, 2H), 7.56(d, J=6.2 Hz, 1H), 7.37(d, J=7.7 Hz, 1H), 7.32(d, J=7.8 Hz, 2H), 6.82(s, 1H), 2.47(s, 3H)	167.33, 164.92, 164.04, 143.35, 137.85, 136.61, 133.92, 132.35, 131.84, 130.05, 129.20, 129.12, 127.75, 127.12, 125.01, 124.96, 124.34, 120.18, 118.62, 71.61, 21.18
6c	11.02(s, 1H), 8.10(d, J=7.9 Hz, 1H), 8.05(d, J=7.7 Hz, 1H), 8.00(t, J=8.1 Hz, 3H), 7.84—7.78(m, 2H), 7.77—7.73(m, 1H), 7.47(d, J=7.3 Hz, 2H), 7.14(d, J=8.8 Hz, 2H), 6.82(s, 1H), 3.88(s, 3H)	164.77, 163.51, 162.64, 138.73, 136.79, 135.24, 134.28, 134.18, 133.39, 131.54, 130.67, 129.73, 128.85, 125.46, 124.16, 123.41, 120.34, 119.06, 114.07, 71.53, 55.51
6d	9.20(s, 1H), 8.91—8.75(m, 2H), 8.33(dt, J=7.9, 1.7 Hz, 1H), 8.12(t, J=7.6 Hz, 2H), 7.97(d, J=8.6 Hz, 1H), 7.71(t, J=7.7 Hz, 1H), 7.63(dd, J=5.5, 3.2 Hz, 2H), 7.50(d, J=7.9 Hz, 2H), 7.36(t, J=7.9 Hz, 1H), 6.79(s, 1H)	165.65, 164.92, 163.92, 152.94, 147.75, 137.54, 136.55, 135.40, 134.15, 132.48, 131.76, 130.26, 129.12, 126.75, 125.09, 124.71, 124.50, 123.50, 120.27, 118.35, 71.57
6e	10.52(s, 1H), 8.06(d, J=8.3 Hz, 1H), 8.01(d, J=7.5 Hz, 1H), 7.96(d, J=7.4 Hz, 1H), 7.82(d, J=8.3 Hz, 1H), 7.80—7.73(m, 2H), 7.67(d, J=7.3 Hz, 1H), 7.43(t, J=7.3 Hz, 1H), 6.66(s, 1H), 2.12(s, 3H)	169.64, 164.77, 163.19, 138.61, 136.72, 134.21, 133.37, 131.44, 130.66, 128.78, 125.97, 125.41, 124.07, 120.33, 118.97, 71.25, 20.45
Compd.	¹H NMR(400 MHz), δ^a	¹³C NMR(100 MHz), δ^b
6f	8.68(s, 1H), 8.06(d, J=8.7 Hz, 1H), 7.91(dd, J=8.0, 4.7 Hz, 4H), 7.60(dd, J=8.9, 5.5 Hz, 4H), 7.48(dd, J=16.5, 8.6 Hz, 3H), 6.70(s, 1H)	167.03, 164.66, 163.18, 137.41, 134.97, 133.97, 132.64, 132.58, 131.28, 130.58, 130.27, 130.22, 128.64, 128.54, 127.08, 124.93, 124.41, 121.63, 119.63, 71.37
6g	8.74(s, 1H), 8.04(d, J=8.7 Hz, 1H), 7.87(dd, J=5.1, 3.2 Hz, 2H), 7.80(d, J=8.2 Hz, 2H), 7.63—7.56(m, 3H), 7.48(dd, J=8.4, 3.6 Hz, 1H), 7.22(d, J=8.0 Hz, 2H), 6.65(s, 1H), 2.41(s, 3H)	167.35, 165.12, 163.71, 143.83, 137.90, 135.44, 134.39, 133.03, 131.70, 130.98, 130.63, 129.60, 129.09, 127.85, 127.59, 125.47, 124.82, 122.06, 120.11, 71.82, 21.65
6h	8.57(s, 1H), 8.08(d, J=8.7 Hz, 1H), 7.93(dd, J=14.0, 5.6 Hz, 4H), 7.64(tt, J=7.4, 4.1 Hz, 3H), 7.57—7.50(m, 1H), 6.95(d, J=8.8 Hz, 2H), 6.72(s, 1H), 3.90(s, 3H)	166.96, 165.17, 163.80, 163.45, 138.04, 135.51, 134.39, 133.02, 131.80, 131.03, 130.64, 129.63, 129.12, 125.53, 124.85, 122.94, 122.11, 120.25, 114.22, 71.93, 55.52
6i	11.43(s, 1H), 9.17(s, 1H), 8.88(d, J=4.0 Hz, 1H), 8.44—8.28(m, 1H), 8.14(dd, J=8.7, 2.9 Hz, 1H), 8.03—7.98(m, 2H), 7.91(dd, J=8.7, 2.6 Hz, 1H), 7.82(t, J=7.0 Hz, 1H), 7.76(t, J=7.3 Hz, 1H), 7.67(d, J=3.0 Hz, 1H), 7.59(d, J=7.4 Hz, 1H), 6.85(s, 1H)	165.14, 164.78, 162.24, 153.25, 148.63, 138.34, 135.68, 135.58, 134.26, 133.75, 131.19, 130.89, 129.62, 128.06, 125.78, 124.31, 123.99, 122.41, 120.46, 99.50, 71.46
6j	10.60(s, 1H), 8.06(d, J=8.7 Hz, 1H), 7.95(d, J=7.9 Hz, 2H), 7.83(t, J=7.5 Hz, 2H), 7.76(d, J=7.1 Hz, 1H), 7.64(d, J=7.5 Hz, 1H), 6.64(s, 1H), 2.11(s, 3H)	169.93, 164.86, 162.14, 138.25, 135.48, 134.07, 133.63, 131.04, 130.83, 129.59, 127.93, 125.93, 124.18, 122.34, 120.50, 71.18, 20.34

Table 3 Optimization of the reaction conditionsa

Entry	Catalyst	Catalyst loading(%, molar fraction)	Solvent	Volume ratio of EtOH to H₂O	Yield^b(%)
1	—	—	EtOH/H₂O	1:1	Trace
2	Nano TiO₂	5	EtOH	—	32
3	Nano TiO₂	5	MeOH	—	20
4	Nano TiO₂	5	H₂O	—	40
5	Nano TiO₂	5	EtOH/H₂O	5:1	55
6	Nano TiO₂	5	EtOH/H₂O	3:1	64
7	Nano TiO₂	5	EtOH/H₂O	1:1	89
8	Nano TiO₂	5	EtOH/H₂O	1:3	71
9	Nano TiO₂	5	EtOH/H₂O	1:5	40
10	Nano TiO₂	3	EtOH/H₂O	1:1	66
11	Nano TiO₂	8	EtOH/H₂O	1:1	89
12	Nano TiO₂	10	EtOH/H₂O	1:1	89
13	Nano TiO₂	12	EtOH/H₂O	1:1	89

Table 4 One-pot synthesis of isoindolo[2,1-a]quinazolinone and quinazolino[2,1-b] phthalazine-5,8-dione derivatives

Entry	Compd.	R¹	R²	R³	Yield^*(%)
1	5a	H	H	—	89
2	5b	H	OCH₃	—	93
3	5c	H	Cl	—	85
4	5d	Cl	H	—	80
5	5e	Cl	OCH₃	—	85
6	5f	Cl	Cl	—	80
7	6a	H	—	Ph	83
8	6b	H	—	4-CH₃-Ph	91
9	6c	H	—	4-OCH₃-Ph	90
10	6d	H	—	3-Pyridyl	79
11	6e	H	—	CH₃	80
12	6f	Cl	—	Ph	81
13	6g	Cl	—	4-CH₃-Ph	87
14	6h	Cl	—	4-OCH₃-Ph	87
15	6i	Cl	—	3-Pyridyl	73
16	6j	Cl	—	CH₃	79

Scheme 2 Proposed formation mechanism of compounds 5 and 6

Fig.1 Recyclability of the catalyst for the one-pot synthesis of compound 5a under the optimal reaction

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纳米TiO₂催化一锅法合成喹唑啉酮并酞嗪酮及3-酰胺基异吲哚酮并喹唑啉酮类化合物

TiO₂ Nanoparticles-catalyzed One-pot Synthesis of Quinazolino[2,1-b]phthalazin-8-one and 3-Acylamino Isoindolo[2,1-a]quinazoline Derivatives^†

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