Synthesis of 3,4-Dihydro-2H-pyrido[1,2-b]isoindol-1-one and 3,4-Dihydro-2H-pyrido[1,2-b]pyrrolidin-1-one Functionalized at the C-6 Position by an Intramolecular Horner-Wadsworth-Emmons Reaction

Abstract

Novel polyheterocycles were prepared from a new annellation reaction which proceeds by nucleophilic substitution followed by an intramolecular Horner‐Wadsworth‐Emmons reaction between imides and β‐functionalized phosphonates.

Pyrido- and pyrimidoisoindoles: methods of synthesis and properties

“…Tel. (38)(39)(40)(41)(42)(43)(44)) 239 34 93. E-mail: palek@mail.univ.kiev.ua (A A Pokholenko), z_voitenko@mail.univ.kiev.ua (Z V Voitenko), vkovtunenko@mail.univ.kiev.ua (V A Kovtunenko) A heptacyclic heteroaromatic system with a junction nitrogen atom containing a pyrido[2,1-a]isoindole fragment has been synthesised.…”

Cyclization Strategies Using Imide Derivatives for the Synthesis of Polycyclic Nitrogen‐Containing Compounds

“…Additional examples of intramolecular Wittig reactions using imides involved the preparation of isoindolo analogues of batracylin and their biological evaluation, which showed some promising results [79] (not shown). Furthermore, the Horner‐Wadsworth‐Emmons (HWE) olefination using imides has been also explored, as reported by Couthon and co‐workers, [80] among other variations [81] …”

“…A representative example of a carbo-rhodination reaction, followed by a cyclization event onto a phthalimide ring. also explored, as reported by Couthon and co-workers, [80] among other variations. [81] Also in the context of olefination reactions, carbanions αstabilized by a sulfoxide or a sulfone group have been employed within cyclization reactions with cyclic imides.…”

Applications of the Horner–Wadsworth–Emmons Olefination in Modern Natural Product Synthesis

“…At the being of the 1970s the HWE reaction was examined a synthetic tool in the synthesis of lactones, 39 lactams, 40 macrocycles, 41 and hetero-polycycles. 42 Since then, intramolecular HWE-based cyclization reactions have become very popular in natural product total synthesis due to their functional group tolerance, high yields, and selectivity. 43…”