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Current Organic Chemistry


ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

Review Article

Prins-Friedel-Crafts Cyclization: Synthesis of Diversely Functionalized Six- Membered Oxacycles

Author(s): Snigdha Roy*

Volume 25 , Issue 5 , 2021

Published on: 13 January, 2021

Page: [635 - 651] Pages: 17

DOI: 10.2174/1385272825666210114105020

Price: $65


Prins cyclization is a well-established synthetic protocol to generate a wide range of important oxygen heterocycles. It is a cyclization reaction performed by an oxocarbenium ion that undergoes an intramolecular pi-bond attack to construct a new carbon-carbon bond. When this cyclization process is conjugated with Friedel-Crafts reaction, it further expands the synthetic potential by fabricating two different carbon-carbon bonds in one single reaction. Different acid catalysts mediated the coupled Prins-Friedel-Crafts reaction which is conducted both in stepwise as well as in tandem fashion. In the stepwise route, three different reacting components were utilized whereas, the tandem methodology required proper modification of the initial substrate molecule. An array of allylic, propargylic, other related alkenols, and carbonyl reactants were employed to carry out the cyclization process. Several oxygenated heterocycles equipped with diverse functionalities were constructed in a stereoselective manner which again reinforced the significance of this cyclization protocol undoubtedly. The present mini-review highlights the utilization of different one-pot stepwise Prins-Friedel-Crafts reactions and the subsequent development of cascade Prins- Friedel-Crafts cyclization process to furnish intricate molecular architectures of vital six-membered oxacycles.

Keywords: Prins-Friedel-Crafts reaction, homoallylic alcohol, homopropargylic alcohol, oxocarbenium ion, acid catalyst, six-membered oxygen heterocycles.

Graphical Abstract
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