A Simple and Efficient Synthesis of Highly Substituted Indeno[1,2-b]pyrrole and Acenaphtho[1,2-b]pyrrole Derivatives by Tandem Three-Component Reactions

Abstract

A green, convenient and tandem procedure for the efficient synthesis of highly substituted indeno[1,2-b]pyrrole and acenaphtho[1,2-b]pyrrole derivatives by domino three-component reaction of tryptamine/benzylamine, 1,3-dicarbonyl compounds and ninhydrin/ acenaphthenequinone is described. The significant features of this procedure were characterized by mild reaction conditions, high yields, operational simplicity and it being environmentally benign.

A Review on Covalent Organic Frameworks as Artificial Interface Layers for Li and Zn Metal Anodes in Rechargeable Batteries

“…Therefore, photocatalytic synthesis based on MCRs not only enriches the synthesis methods of COFs but also provides a viable green approach to obtaining COFs with different functions. [ 88 ]…”

Ultrasound promoted three‐component synthesis of dihydroindeno[1,2‐b]pyrrole derivatives

“…White solid (0.35 g, 92%); m.p. 101–103°C (lit: 72–73°C) [14]. FT‐IR (KBr, ν, cm −1 ): 3445, 3075, 2980, 2933, 1718, 1640, 1551, 1460, 1298, 1171.…”

“…The biomedical significances of above structures have motivated the growth and promotion of varied methods for designing and synthesizing dihydroindeno[1,2‐ b ]pyrroles. Dihydroindeno[1,2‐ b ]pyrroles have been synthesized through three types of reactions: (1) a one‐pot three‐component reaction of ninhydrin, primary amine, and an electrophile such as 1,3‐dicarbonyls [13, 14], dialkylacetylenedicarboxylates [12, 15], alkyl propiolates [16], and 1,1‐bis(methylthio)‐2‐nitroethene [17, 18], (2) two‐component reaction between ninhydrin and different enamines [9–11, 19–21], and (3) a one‐pot reaction of ninhydrin, primary amines (two moles), and diketene [22]. Hence, different methods have been developed to achieve title heterocycles [10, 14, 23], for example ball‐milling [24], grinding [25], and microwave irradiation [20] [26], in the presence of various homogeneous [11, 21, 27] or heterogeneous [28] catalysts.…”

“…Dihydroindeno[1,2‐ b ]pyrroles have been synthesized through three types of reactions: (1) a one‐pot three‐component reaction of ninhydrin, primary amine, and an electrophile such as 1,3‐dicarbonyls [13, 14], dialkylacetylenedicarboxylates [12, 15], alkyl propiolates [16], and 1,1‐bis(methylthio)‐2‐nitroethene [17, 18], (2) two‐component reaction between ninhydrin and different enamines [9–11, 19–21], and (3) a one‐pot reaction of ninhydrin, primary amines (two moles), and diketene [22]. Hence, different methods have been developed to achieve title heterocycles [10, 14, 23], for example ball‐milling [24], grinding [25], and microwave irradiation [20] [26], in the presence of various homogeneous [11, 21, 27] or heterogeneous [28] catalysts. In addition, many attempts have been made in recent years to synthesize interesting derivatives of dihydroindeno[1,2‐ b ]pyrroles such as compounds bearing bistriazole unit [29] and functionalized dimers [30].…”

Multicomponent Reactions

“…Indeno[1,2- b ]pyrroles and acenaphtho[1,2- b ]pyrroles possess interesting biological activities, also as inhibitors of important human enzymes and receptors. A domino three-component reaction for the synthesis of these derivatives was described by Jing Wang and coworkers [4] through a green, efficient, and convenient procedure, characterized by mild reaction conditions, high yields, and operational simplicity.…”