Applications of aminocarbazoles in heterocyclic synthesis

Abstract

Aminocarbazoles are versatile building blocks in organic synthesis. This review focuses on the application of aminocarbazoles to generate a large variety of fused carbazole heterocycles such as pyridocarbazoles, isomeric pyridocarbazoles, thiazolocarbazoles, pyrimidocarbazoles, pyrrolocarbazoles, indolocarbazoles, quino-and chromeno-carbazoles and many others. Many of these molecules exhibit promising biological activities.

Progress in the chemistry of 3-amino-9-ethylcarbazole

“…Wang et al 21 recently reported the synthesis of 2-(3-(9-ethyl-9H -carbazol-3-yl))ureido)ethyl methacrylate (14), a purple fluorescent monomer, via the nucleophilic addition reaction of 3-amino-9-ethylcarbazole (12) with 2-isocyanatoethyl methacrylate (13) in methylene chloride at room temperature (Scheme 4). The obtained monomer 14 exhibits a broad range of material applications such as functional coatings, optical devices, chemosensors, organic LEDs, and laser active media.…”

“…Among the substituted carbazoles, 3-aminocarbazole plays a significant role in the field of medicinal chemistry, where it is applied as a versatile precursor for the synthesis of several bioactive annulated carbazole derivatives. 14 3-Aminocarbazoles are also considered useful substrates in the synthesis of various dyes and pigments, stabilizers for polymers, pesticides, photographic materials, and diagnostic reagents in cytochemical studies. For instance, 3-amino-9-ethylcarbazole has been widely used as a peroxidase and considered suitable for the colorimetric detection of antibodies in the diagnosis of certain diseases.…”

Transition-Metal-Free Access to Pyridocarbazoles from 2-Alkynylindole-3-carbaldehydes via Azomethine Ylide

“…Heteroannulated carbazole framework is an important core motif present in a wide range of natural products and pharmaceutically derived drugs . Among them, pyridocarbazoles are an integral part of numerous natural products, bioactive alkaloids, and pharmaceuticals .…”

Synthesis, molecular docking and in vitro antiproliferative activity of novel pyrano[3,2-c]carbazole derivatives

“…[33][34][35][36][37] These reactions provide a rapid synthetic route for assembling polycyclic structures. [38][39][40] As a part of our interest in carbazole heterocycles, 41,42 here we wish to report a new series of polycyclic pyrano [3,2-c]carbazole derivatives by domino Knoevenagelhetero-Diels-Alder reactions.…”