Methods for the construction of [1,2]isoindolo-condensed benzazepines, benzazocines, quinolines, and isoquinolines. 1. Isoindolobenzazepines, isoindolobenzazocines. (Review)

Abstract

Data on methods for the construction of tetracyclic systems in which an isoindole ring is condensed with benzazepines and benzazocines on the [1,2] side are reviewed. The reaction conditions and approaches leading to isoindolobenzazepines and isoindolobenzazocines are discussed. Examples of the synthesis of physiologically active natural alkaloids with the structure of the above-mentioned condensed isoindoles are presented. Data for 1959Data for -2004 The interest in the development of methods for the synthesis of tetracyclic structures in which an isoindole fragment is annelated with quinoline, isoquinoline, or benzazepine fragments is due to the wide spectrum of physiological activity and the widespread occurrence of such structures in nature.In spite of the considerable amount of experimental data there are no papers summarizing methods for the construction of such structures.In the present review data on the synthesis of isoindolobenz-3-and isoindolobenz-2-azepines, isoindoloazocines, isoindoloquinolines, and isoindoloisoquinolines are examined systematically. The review is structured in this way because isoindolo[1,2-b]benz-3-azepines form the main structural fragment in a large number of alkaloids and the available information on their synthesis is the most comprehensive. In addition to the methods of synthesis, the review contains certain information on the occurrence of the condensed isoindoles in nature and on their physiological activity.

5‐Amido‐ and 5‐Amino‐Substituted Epoxyisoindolo[2,1‐a]tetrahydroquinolines and 10‐Carboxylic Acids: Their Synthesis and Reactivity

“…These approaches, as a rule, are notable for the low availability of starting compounds and for moderate yield of target products. All earlier methods of isoindoloquinolines synthesis were summarized in our review [2]. At the same time, such close attention to this system is related to the high and diverse biological activity of derivatives containing an isoindolo[2,1‐ a ]quinoline core [3].…”

Intramolecular Chemoselective Acylation of a Suitably Substituted Isoindole: Synthesis of (±)-Chilenine and (±)-Deoxychilenine

“…Chilenine (1), deoxychilenine (2), and lennoxamine 3were isolated, respectively, from Berbelis empetrifolia, Berbelis actinacantha, and Berbelis darwinii 1 and they belong to the isoindolobenzazepine class of alkaloids ( Figure 1). 2 These natural products are biogenetically related to protoberberines, hence their ring systems are accessible by oxidation of berberine alkaloids.…”

Investigations in the field of benzoxa- zines. 15*. Tandem heterocyclizations with the participion of 2-formylbenzoic acid. The synthesis of isoindolo[1,2-b][1, 3]- and -[2,1-a][1, 3]benzoxazinones

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Keywords: 2-(1-aminoalkyl)phenols, 2-aminophenylcarbinols, 10H-isoindolo[1,2-b][1,3]benzoxazin-12(4bH)-ones, 5H-isoindolo[2,1-a][3,1]benzoxazin-11(6aH)-ones, 2-formylbenzoic acids.Tetracyclic condensed structures containing an annelated isoindole fragment are widely distributed in nature and have a broad spectrum of biological activity that is well reflected in recent reviews [2,3]. Hence there is much interest in developing new routes for their synthesis.

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“…Tetracyclic condensed structures containing an annelated isoindole fragment are widely distributed in nature and have a broad spectrum of biological activity that is well reflected in recent reviews [2,3]. Hence there is much interest in developing new routes for their synthesis.…”