Synthesis and Spectral Characterization of Benzo-[6,7][1,5]diazocino[2,1-a]isoindol-12-(14H)-one Derivatives

Abstract

Abstract:A simple synthetic route affording 27%-85% yields of benzo [6,7][1,5]diazocino[2,1-a]isoindol-12(14H)-one ring systems from readily available 3-(2-oxo-2-phenylethyl) isobenzofuran-1(3H)-ones and 2-(aminomethyl)aniline starting materials in toluene and catalysed by p-toluenesulfonic acid is developed. The 1 H-and 13 C-NMR spectra of the final products were assigned using a variety of one and two-dimensional NMR experiments. The distinction between the two potential isomers of the final products was made on the basis of heteronuclear multiple bond connectivity (HMBC) NMR spectra.

Aniline-Promoted Synthesis of Isobenzofuranone Derivatives

“…The compounds with isobenzofuranone skeleton 截至目前，文献报道了多种异苯并呋喃酮骨架化合物的合成方法，根据反应物的种类和反应条件的不同，主要 可以分为几类，如 Figure 2 所示。其中，路线 A 所示的合成方法不仅需要使用 Pd 催化剂，而且繁琐的后处理以及 较低的收率并不符合化学反应的原子经济性原则 [9] 。如路线 B 所示的合成方法中，较低的收率，反应底物的局限性 以及高达 30 h 的反应时间也使得该合成方法的应用受到限制 [10] 。而路线 C 作为传统的异苯并呋喃酮骨架的合成方 法，尽管所需条件较温和，但涉及多步反应和纯化 [11] 。路线 D 所示的合成方法，虽然具有良好的官能团容受性和较 高的收率，但是涉及稀有金属催化 [12] 。而路线 E [13] , F [14] , G [15] 所示的合成方法尽管能在较少的反应时间内以较高收 率得到目标产物，但是路线 E, G 中需要使用特殊的纳米催化剂和布朗斯特酸离子液体，路线 F 中的微波反应对仪 器的要求使其具有一定的局限性， 同时需要使用固体强酸催化剂以促进反应的进行。 最新报道的合成方法路线 H [16] ， 尽管反应条件温和，使用了弱酸苯硼酸作为催化剂，但是较长的反应时间以及较低的收率使得该合成方法具有一定 的局限性。通过比较异苯并呋喃酮骨架的各类合成方法，不难发现，尽管该类化合物合成方法多样，但是多数反应 需使用特殊催化剂，且后处理繁杂，部分方法更是以较长的反应时间和较低的收率得到目标产物。因此，异苯并呋 喃酮骨架的构建新方法仍是一个值得探究的课题 [17] 。本文首次报道了苯胺促进的异苯并呋喃酮衍生物的合成新方 法，该方法具有条件温和、底物适用范围广、产物收率高和后处理简洁高效等优点，为合成异苯并呋喃酮类化合物 提供了简便的新途径。 图 2 各种异苯并呋喃酮类化合物的合成方法…”

N-{2-[(3-Oxo-1,3-dihydro-2-benzofuran-1-yl)acetyl]phenyl}acetamide

“…More precisely, some phthalide derivatives have been evaluated as antioxidant 1 [1], anti-HIV-1 2 [2], antileishmanial 3 [3] and antifungal 4 [4] while other phthalides are known for their herbicidal properties 5 [5] (Figure 1). Additionally, phthalide derivatives are important intermediates in the synthesis of other relevant heterocyclic systems, as is the case for 2,3-dihydro-1H-isoindol-1-one derivatives, which are another type of unique molecules [6][7][8][9] (Scheme 1). Additionally, phthalide derivatives are important intermediates in the synthesis of other relevant heterocyclic systems, as is the case for 2,3-dihydro-1H-isoindol-1-one derivatives, which are another type of unique molecules [6][7][8][9] (Scheme 1).…”

“…Additionally, phthalide derivatives are important intermediates in the synthesis of other relevant heterocyclic systems, as is the case for 2,3-dihydro-1H-isoindol-1-one derivatives, which are another type of unique molecules [6][7][8][9] (Scheme 1). Additionally, phthalide derivatives are important intermediates in the synthesis of other relevant heterocyclic systems, as is the case for 2,3-dihydro-1H-isoindol-1-one derivatives, which are another type of unique molecules [6][7][8][9] (Scheme 1). Herein, we carried out the synthesis of a phtalide derivatives based on a Claisen-Smichdt reaction.…”