CN111072611B - 一种苯并呋喃亚胺内酯衍生物的合成方法 - Google Patents

一种苯并呋喃亚胺内酯衍生物的合成方法 Download PDF

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CN111072611B
CN111072611B CN201911323588.3A CN201911323588A CN111072611B CN 111072611 B CN111072611 B CN 111072611B CN 201911323588 A CN201911323588 A CN 201911323588A CN 111072611 B CN111072611 B CN 111072611B
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何炜
刘慧霞
邓晓军
张俊娜
张邦乐
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Fourth Military Medical University FMMU
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Abstract

本发明公开了结构通式（I）所示的苯并呋喃亚胺内酯衍生物的合成方法，其以结构式（II）所示的邻烯烃苯甲酰胺类分子为底物，加入催化当量的碘试剂/氧化剂催化体系，或三价碘苯体系，以路易斯酸为添加剂，室温反应一步构建结构式（I）所示的苯并呋喃亚胺内酯化合物。本发明无需金属催化反应，避免了毒副作用大的过渡金属的使用；反应条件温和，可以在空气、室温条件下进行；反应时间短，30分钟内反应即可完成；操作简单，底物适用范围广。

Description

一种苯并呋喃亚胺内酯衍生物的合成方法
技术领域
本发明涉一种合成苯并呋喃亚胺内酯类化合物的方法，特别是一种基于烯烃的碳氧（C(sp 2 )-O）键形成反应，合成苯并呋喃亚胺内酯类化合物的新方法，属于有机合成技术领域。
背景技术
亚胺内酯类衍生物是一类重要的有机合成中间体，且具有较为广泛的生物活性，在生命科学和医药领域具有广阔的应用前景。例如：具有亚胺内酯结构的棉籽酚衍生物，具有更好的抗HIV-I型病毒活性；具有亚胺内酯结构罗丹明类的荧光检测剂可用于检测细胞内的多种小分子化合物及蛋白；具有亚胺内酯结构的除草剂。此外，亚胺内酯类化合物还可用于高分子材料聚酰亚胺和聚异酰亚胺的合成，进一步转化可以合成一些药物分子，例如丁苯肽，是治疗轻中度急性缺血性脑卒中的一类药物。
关于亚胺内酯的合成，最早可追溯到上个世纪80年代。日本的Yoshihiko Ito教授课题组 (J. Org. Chem.1982, 47, 741-743) 以ß-不饱和碳基化合物与异氰基化合物为起始原料，在化学计量的二乙基氯化铝的作用下通过[4+1]环加成反应得到3这种亚胺内酯类化合物，化合物3经过简单的还原，水解，可以得到γ-丁内酯类化合物5。这类结构是一些药物分子，例如苦薄荷素，竹柏内酯的基本骨架结构。但这种合成方法仅能得到有限的产物，且需要用到剧毒性的异氰基类化合物作为反应底物，限制了其应用。
Figure DEST_PATH_IMAGE002
近年来，以芳炔，异氰酸酯与醛酮为底物的“三组分合成法”被广泛应用于苯并呋喃亚胺内酯类化合物的合成，Yoshida (Angew. Chem., Int. Ed.2004, 43, 3935-3938;Tetrahedron2007, 63, 4793-4805; Angew. Chem., Int. Ed.2011, 50, 4488-4491),Stoltz (Heterocycles2012, 86, 933-940)和Nishihara (Organometallics2014, 33,3500-3507)课题组分别报道了芳炔、异氰酸酯与醛/酮、乙酸苯酯、氰基甲酸盐的三组分偶联反应，得到了苯并呋喃亚胺内酯类化合物。该方法有效扩展了亚胺内酯类化合物的范围，但仍然使用了剧毒性的异氰基化合物作为反应底物。
近年来，以邻炔烃苯甲酰胺为底物的分子内选择性环化反应，可代替羰基组分和芳炔，成为合成取代的邻烯烃苯并呋喃亚胺内酯的有效的合成方法（Org. Lett.2016, 18,4814-4817; Chem. Commun.2017, 53, 5279-5282; Org. Biomol. Chem.2019, 17,4335-4341）。但由于酰胺的两种互变结构以及炔烃的选择性，应用该类底物可能会得到四种结构类型的产物，选择性较差。且需要一些昂贵的金属，例如Au，Pa等作催化剂。
发明内容
本发明的目的是提供一种工艺简单、反应条件温和、选择性高的合成苯并呋喃亚胺内酯类化合物的新方法。
本发明实现过程如下：
一种苯并呋喃亚胺内酯衍生物的合成方法，
Figure DEST_PATH_IMAGE004
以结构式（II）所示的邻烯烃苯甲酰胺类分子为底物，加入催化当量的碘试剂/氧化剂催化体系，或三价碘苯体系，以路易斯酸为添加剂，室温反应一步构建结构式（I）所示的苯并呋喃亚胺内酯化合物，
其中：R选自苯基、苄基、C1~C7的烷基，或取代的苯基或苄基，所述取代的苯基或苄基中的取代基为C1~C7的烷基、C1~C7的烷氧基、卤素、硝基、三氟甲基；
R1选自氢、C1~C7的烷基、C1~C7的烷氧基、卤素、三氟甲基，硝基；
R2选自氢，C1~C7的烷基，C1~C7的烷氧基、卤素、三氟甲基，硝基、苯基、苄基，或取代的苯基或苄基，所述取代的苯基或苄基中的取代基为C1~C7的烷基、C1~C7的烷氧基、卤素、硝基、三氟甲基。
所述的氧化剂选自过硫酸氢钾，间氯过氧苯甲酸。
所述的路易斯酸选自三氟化硼乙醚，甲基磺酸，三氟乙酸。
所述的碘试剂为碘单质，以及碘化钾或芳基碘，所述芳基碘中的芳基为 C1-C7的烷基，C1-C7的烷氧基、卤素、硝基或乙酰基取代的苯基或萘基。
本发明的优点在于，无需金属催化反应，避免了毒副作用大的过渡金属的使用；反应条件温和，可以在空气、室温条件下进行；反应时间短，30分钟内反应即可完成；操作简单，底物适用范围广。
具体实施方式
下面通过实施例对本发明进行详述，但本发明并不限于这些实施例。
实施例1通式（I）中化合物I-1 的合成
Figure DEST_PATH_IMAGE006
向装有磁子的反应试管中加入对甲基碘苯（10 mol%），间氯过氧苯甲酸（1.5equiv）和乙腈（2.0 mL）。然后再加入邻烯烃苯甲酰胺底物（0.2 mmol, 1.0 equiv），三氟化硼乙醚（1.5 equiv）。反应混合物室温条件下继续搅拌30分钟。 通过薄层色谱检测反应过程。反应完成后，将反应液直接湿法上样，通过1/5的碱性氧化铝，4/5的硅胶（200-300目）柱快速纯化，得到苯并呋喃亚胺内酯类化合物I-1。产物结构经1H NMR, 13C NMR 和HRMS确证。
产物结构表征：
Figure DEST_PATH_IMAGE008
(Z)-3-methylene-N-phenylisobenzofuran-1(3H)-imine (I-1). Colorlessoil (39.8 mg, 90%); 1H NMR (400 MHz, CDCl3) δ 7.98 (dt, J = 7.6, 1.2 Hz, 1H),7.68 – 7.58 (m, 1H), 7.58 – 7.48 (m, 1H), 7.45 – 7.31 (m, 3H), 7.16 (tt, J =6.8, 2.0 Hz, 1H), 5.00 (s, 2H); 13C NMR (100 MHz, CDCl3) δ 155.1, 153.9,145.7, 136.2, 132.2, 130.8, 130.2, 128.8 (2C), 124.7, 123.7 (2C), 123.6,120.3, 87.2; HRMS: [M+H]+ calcd for C15H11NO 222.0913, found 222.0912。
实施例2
使用与实施例1相同方法，通过改变底物结构，可以得到下述化合物。
Figure DEST_PATH_IMAGE010
(Z)-N-(2,6-dimethylphenyl)-3-methyleneisobenzofuran-1(3H)-imine (I-2). Colorless oil (41.5 mg, 83%); 1H NMR (400 MHz, CDCl3) δ 8.04 (d, J = 6.8Hz, 1H), 7.63 (t, J = 7.6 Hz, 2H), 7.59 – 7.52 (m, 1H), 7.08 (d, J = 7.6 Hz,2H), 6.97 (t, J = 7.6 Hz, 1H), 4.97 – 4.89 (m, 2H), 2.17 (s, 6H); 13C NMR (100MHz, CDCl3) δ 154.8, 153.1, 144.6, 136.8, 135.2, 134.5, 132.3, (130.3, 130.2)(1C), (129.7, 129.8) (1C), (128.2, 127.9) (1C), 127.7 (2C), (123.7, 123.5)(1C) 120.36, 87.11, 18.37 (2C); HRMS: [M+H]+ calcd for C17H15NO 250.1226, found250.1227。
Figure DEST_PATH_IMAGE012
(Z)-3-methylene-N-(m-tolyl)isobenzofuran-1(3H)-imine (I-3). Colorlessoil (37.1 mg, 79%); 1H NMR (400 MHz, CDCl3) δ 7.97 (d, J = 7.6 Hz, 1H), 7.64(d, J = 7.6 Hz, 1H), 7.56 (dt, J = 19.6, 6.8 Hz, 2H), 7.31 – 7.23 (m, 1H),7.17 (d, J = 7.6 Hz, 2H), 6.98 (d, J = 7.6 Hz, 1H), 4.99 (t, J = 2.4 Hz, 2H),2.38 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 155.1, 153.7, 145.6, 138.5, 136.2,132.1, 130.8, 130.1, 128.5, 125.5, 124.2, 123.5, 120.5, 120.2, 87.1, 21.5;HRMS: [M+H]+ calcd for C16H13NO 236.1070, found 236.1071。
Figure DEST_PATH_IMAGE014
(Z)-N-(4-methoxyphenyl)-3-methyleneisobenzofuran-1(3H)-imine (I-5).White solid (39.2 mg, 78%);1H NMR (400 MHz, CDCl3) δ 7.96 (dt, J = 7.2, 1.2Hz, 1H), 7.65 (dt, J = 8.0, 1.2 Hz, 1H), 7.56 (dtd, J= 18.4, 7.2, 1.2 Hz,2H), 7.50 – 7.41 (m, 2H), 6.96 – 6.90 (m, 2H), 5.06 – 4.97 (m, 2H), 3.84 (s,3H); 13C NMR (100 MHz, CDCl3) δ 157.0, 155.2, 152.8, 138.5, 135.9, 131.8,131.2, 130.1, 125.7 (2C), 123.4, 120.2, 114.0 (2C), 86.6, 55.4; HRMS: [M+H]+calcd for C16H13NO2 252.1019, found 252.1020。
Figure DEST_PATH_IMAGE016
(Z)-N-(4-fluorophenyl)-3-methyleneisobenzofuran-1(3H)-imine (I-6).Colorless oil (39.2 mg, 82%); 1H NMR (400 MHz, CDCl3) δ 7.96 (d, J= 7.6 Hz,1H), 7.65 (d, J = 7.6 Hz, 1H), 7.57 (dt, J= 22.0, 7.2 Hz, 2H), 7.39 (dd, J =8.8, 5.2 Hz, 2H), 7.06 (t, J= 8.8 Hz, 2H), 5.02 (s, 2H); 13C NMR (100 MHz,CDCl3) δ 161.3, 158.9, 155.1, 153.8, (141.6, 141.5) (1C), 136.1, 132.2,130.7, 130.2, (125.6, 125.5) (1C), 123.5, 120.3, 115.5, 115.3, 87.2; 19F NMR(376 MHz, CDCl3) δ -118.1; HRMS: [M+H]+ calcd for C15H10FNO 240.0819, found240.0823。
Figure DEST_PATH_IMAGE018
(Z)-N-benzyl-3-methyleneisobenzofuran-1(3H)-imine (I-7). White solid(37.6 mg, 78%); 1H NMR (400 MHz, CDCl3); δ 7.93 (d, J = 7.6 Hz, 1H), 7.64 (d,J = 7.6 Hz, 1H), 7.57 (t, J = 7.2 Hz, 1H), 7.54 – 7.46 (m, 3H), 7.39 (t, J =7.6 Hz, 2H), 7.32 – 7.28 (m, 1H), 5.06 – 4.96 (m, 2H), 4.90 (s, 2H); 13C NMR(100 MHz, CDCl3) δ 155.4, 155.0, 140.2, 136.5, 131.6, 130.5, 130.0, 128.4(2C), 127.9 (2C), 126.7, 123.2, 120.2, 85.7, 51.7; HRMS: [M+H]+ calcd forC16H13NO 236.1070, found 236.1077。
Figure DEST_PATH_IMAGE020
(Z)-6-methyl-3-methylene-N-phenylisobenzofuran-1(3H)-imine (I-9).Colorless oil (37.6 mg, 80%); 1H NMR (400 MHz, CDCl3) δ 7.78 (s, 1H), 7.52 (d,J = 8.0 Hz, 1H), 7.37 (d, J = 5.6 Hz, 5H), 7.15 (tt, J = 6.4, 2.4 Hz, 1H),4.93 (q, J = 2.8 Hz, 2H), 2.47 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 155.2,154.0, 145.7, 140.7, 133.8, 133.4, 131.1, 128.7(2C), 124.6, 123.7 (2C),123.6, 120.1, 86.3, 21.6; HRMS: [M+H]+ calcd for C16H13NO 236.1070, found236.1071。
Figure DEST_PATH_IMAGE022
(Z)-3-methylene-5-nitro-N-phenylisobenzofuran-1(3H)-imine (I-10).Light yellow solid (47.3 mg, 89%); 1H NMR (400 MHz, CDCl3) δ 8.49 (d, J = 2.0Hz, 1H), 8.39 (dd, J = 8.4, 2.0 Hz, 1H), 8.13 (d, J = 8.4 Hz, 1H), 7.46 –7.36 (m, 4H), 7.22 (tt, J= 6.0, 2.4 Hz, 1H), 5.19 (s, 2H); 13C NMR (100 MHz,CDCl3) δ 153.5, 151.3, 150.6, 144.6, 137.0, 135.8, 128.9 (2C), 125.7, 125.2,124.9, 124.1 (2C), 116.1, 89.8; HRMS: [M+H]+ calcd for C15H10N2O3 267.0764,found 267.0763。
Figure DEST_PATH_IMAGE024
(Z)-1-methylene-N-phenylnaphtho[1,2-c]furan-3(1H)-imine (I-11). Whitesolid (47.7 mg, 88%); 1H NMR (400 MHz, CDCl3) δ 8.27 (d, J = 7.8 Hz, 1H), 8.03– 7.95 (m, 3H), 7.72 – 7.57 (m, 2H), 7.47 – 7.35 (m, 4H), 7.22-7.13 (m, 1H),5.45 (d, J = 3.2 Hz, 1H), 5.32 (d, J= 3.6 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ155.8, 154.1, 145.8, 135.7, 132.1, 131.8, 130.8, 129.7, 128.8 (2C), 128.3,127.8, 127.0, 124.7, 124.0 (2C), 123.7, 119.5, 92.2; HRMS: [M+H]+ calcd forC19H13NO 272.1070, found 272.1271。
Figure DEST_PATH_IMAGE026
(Z)-7-methyl-3-methylene-N-phenylisobenzofuran-1(3H)-imine (I-12).Colorless oil (32.0 mg, 68%); 1H NMR (400 MHz, CDCl3) δ 7.45 (q, J = 8.0 Hz,2H), 7.36 (d, J = 7.2 Hz, 2H), 7.30 (d, J = 8.0 Hz, 3H), 7.14 (t, J = 7.2 Hz,1H), 4.95 – 4.90 (m, 2H), 2.78 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 154.9,154.2, 146.3, 137.8, 136.7, 132.0, 131.6, 128.7 (2C), 127.9, 124.3, 123.4(2C), 117.6, 86.1, 18.6; HRMS: [M+H]+ calcd for C16H13NO 236.1070, found236.1071。
Figure DEST_PATH_IMAGE028
(Z)-4-methyl-3-methylene-N-phenylisobenzofuran-1(3H)-imine (I-13).Colorless oil (37.6 mg, 80%); 1H NMR (400 MHz, CDCl3) δ 7.84 (d, J = 7.6 Hz,1H), 7.42 (t, J = 7.6 Hz, 1H), 7.37 (d, J = 5.6 Hz, 5H), 7.15 (tt, J = 6.0,2.8 Hz, 1H), 5.12 (d, J = 3.2 Hz, 1H), 4.97 (d, J= 3.0 Hz, 1H), 2.52 (s, 3H);13C NMR (100 MHz, CDCl3) δ 155.7, 154.1, 145.9, 134.1, 133.8, 133.5, 131.6,130.0, 128.7 (2C), 124.5, 123.7 (2C), 121.4, 91.3, 20.0; HRMS: [M+H]+ calcdfor C16H13NO 236.1070, found 236.1072。
Figure DEST_PATH_IMAGE030
(Z)-3-((Z)-4-chlorobenzylidene)-N-phenylisobenzofuran-1(3H)-imine (I-14). White solid (46.3 mg, 70%); 1H NMR (400 MHz, CDCl3) δ 8.37 (d, J = 8.0Hz, 1H), 7.55 (t, J = 7.2, 1H), 7.49 (d, J = 8.8 Hz, 2H), 7.41 (dt, J = 15.6,7.8 Hz, 3H), 7.31 (t, J = 9.6 Hz, 3H), 7.22 (d, J = 7.6 Hz, 2H), 7.14 (t, J =7.6 Hz, 1H), 6.69 (s, 1H); 13C NMR (100 MHz, CDCl3) δ 150.6, 149.5, 146.7,135.4, 133.7, 132.5, 130.8, 129.5, 128.9 (2C), 128.8 (2C), 128.4, 127.6,125.9 (2C), 125.7, 123.7, 122.3 (2C), 101.2; HRMS: [M+H]+ calcd for C21H14ClNO332.0837, found 332.0838。
Figure DEST_PATH_IMAGE032
(1Z,3Z)-3-butylidene-N-phenylisobenzofuran-1(3H)-imine (I-15).Colorless oil; (Z:E = 6.7:1); 1H NMR (400 MHz, CDCl3) δ 7.97 (d, J = 7.6 Hz,1H), 7.59 – 7.55 (m, 2H), 7.49 – 7.42 (m, 3H), 7.42 – 7.34 (m, 2H), 7.19 –7.10 (m, 1H), 5.43 (t, J = 7.6 Hz, 1H), 2.37 (q, J = 7.6 Hz, 2H), 1.52 (dt, J= 14.8, 7.2 Hz, 2H), 0.97 (t, J = 7.6 Hz, 3H); 13C NMR (100 MHz, CDCl3) δ154.2, 148.4, 145.8, 136.7, 132.0, 130.3, 129.1, 128.7 (2C), 124.6, 124.2(2C), 123.6, 119.3, 106.7, 29.7, 19.2, 14.1. HRMS: [M+H]+ calcd for C18H17NO264.1383, found 264.1384。

Claims (1)

1.式I所示的苯并呋喃亚胺内酯衍生物的合成方法，其特征在于：
Figure DEST_PATH_IMAGE001
以式II所示的邻烯烃苯甲酰胺类分子为底物，加入催化当量的碘试剂/氧化剂催化体系，以路易斯酸三氟化硼乙醚为添加剂，乙腈为溶剂，室温反应一步构建式I所示的苯并呋喃亚胺内酯化合物，所述碘试剂为对甲基碘苯，氧化剂为间氯过氧苯甲酸，
其中：R选自苯基、苄基、C1~C3的烷基，或取代的苯基或苄基，所述取代的苯基或苄基中的取代基为C1~C3的烷基、C1~C3的烷氧基、卤素、硝基；
R1选自氢、C1~C3的烷基、C1~C3的烷氧基、卤素、硝基；
R2选自氢，C1~C3的烷基，C1~C3的烷氧基、卤素、硝基、苯基、苄基，或取代的苯基或苄基，所述取代的苯基或苄基中的取代基为C1~C3的烷基、C1~C3的烷氧基、卤素、硝基。
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