Microwave‐accelerated Synthesis of Some (±)‐1‐Aryl‐5‐chloroisochromans

The oxa‐Pictet–Spengler cyclization is the oxygen variation of the Pictet–Spengler reaction, in which an aromatic alcohol component (generally a β‐arylethyl alcohol) reacts with acarbonyl component (aldehyde, ketone or their masked derivatives), to yield a 1‐substituted (or 1,1′‐disubstituted)pyran fused to the aromatic ring system found in the starting alcohol. The transformation is usually promoted by Brønsted and Lewis acids. Intramolecular versions of the reaction are also known, where both components are mutually masked as an acetal. Discussed here are aspects concerning the most recent developments and new applications of this useful reaction, including the scope and limitations of new promoters, and new mechanistic pictures of this transformation. The use of novel stereochemical control strategies and the application of the reaction to the synthesis of natural products and their analogs, as well as to accessing fully synthetic bioactive compounds and new ring systems are presented, and chiral versions of the oxa‐Pictet–Spengler are also analyzed.

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“…Saeed and Mumtaz [35] reported the clean and environmentally benign one-pot synthesis of 1-aryl-5-chloroisochromans (13a-j).…”

Section: New Promoters Of the Oxa-pictet-spengler Cyclizationmentioning

confidence: 99%

Synthesis of Oxacycles Employing the Oxa‐Pictet–Spengler Reaction: Recent Developments and New Prospects

2011

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ChemInform Abstract: Microwave‐Accelerated Synthesis of Some (.+‐.)‐1‐Aryl‐5‐chloroisochromans.

Saeed

Mumtaz

2008

ChemInform

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The Pictet–Spengler Reaction: A Powerful Strategy for the Synthesis of Heterocycles

Gholamzadeh

2019

Advances in Heterocyclic Chemistry

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Microwave‐accelerated Synthesis of Some (±)‐1‐Aryl‐5‐chloroisochromans

Abstract: Solventless one-pot synthesis of some new ( ± )-1-aryl-5-chloroisochromans by cyclocondensation of 2-(2-chlorophenyl)ethanol with aromatic aldehydes via an acid catalyzed oxa-Pictet-Spengler reaction under microwave irradiation is described.

Cited by 6 publications

References 23 publications

Synthesis of Oxacycles Employing the Oxa‐Pictet–Spengler Reaction: Recent Developments and New Prospects

Synthesis of Oxacycles Employing the Oxa‐Pictet–Spengler Reaction: Recent Developments and New Prospects

ChemInform Abstract: Microwave‐Accelerated Synthesis of Some (.+‐.)‐1‐Aryl‐5‐chloroisochromans.

The Pictet–Spengler Reaction: A Powerful Strategy for the Synthesis of Heterocycles

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