Synthesis of 1-aryl-2,3-diaroyl cyclopropanes from 1,3,5-triaryl-1,5-diketones and their transformation into ,-1,4-diaryl-1,3-butadienes

A new method for the synthesis of 1-aryl-2,3-diaroyl cyclopropanes has been developed by iodine/DBU-mediated cyclization of 1,3,5-triaryl-1,5-diketones. The alcohols derived by the reduction of these cyclopropanes, when treated with conc. HCl, afforded a series of 1,3-dienes through cyclopropyl ring...

Full description

Saved in:
Bibliographic Details
Published in:RSC advances 2024-07, Vol.14 (31), p.2276-2285
Main Authors: Britto, Kashpar John, Meenakshi, Maniarasu, Srinivasan, Kannupal
Format: Article
Language:
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A new method for the synthesis of 1-aryl-2,3-diaroyl cyclopropanes has been developed by iodine/DBU-mediated cyclization of 1,3,5-triaryl-1,5-diketones. The alcohols derived by the reduction of these cyclopropanes, when treated with conc. HCl, afforded a series of 1,3-dienes through cyclopropyl ring-opening and subsequent fragmentation. Overall, the synthetic sequence represents a new non-Wittig methodology for the synthesis of 1,3-dienes from 1,5-diketones. 1-Aryl-2,3-diaroyl cyclopropanes, synthesized by iodine/DBU-mediated cyclization of 1,3,5-triaryl-1,5-diketones, when subjected to reduction followed by treatment with conc. HCl afforded E , E -1,5-diaryl-1,3-butadienes.
ISSN:2046-2069
DOI:10.1039/d4ra02525c