1,3-Dibromo-1,1-difluoro-2-propanone as a Useful Synthon for a Chemoselective Preparation of 4-Bromodifluoromethyl Thiazoles

[Image: see text] We report herein a synthetic protocol for the preparation of 1,3-dibromo-1,1-difluoro-2-propanone, a new synthon used for the first time in a reaction with aromatic amines and sodium thiocyanate, leading to thiazoles which are useful candidates in drug discovery programs. The new s...

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Autores principales: Colella, Marco, Musci, Pantaleo, Carlucci, Claudia, Lillini, Samuele, Tomassetti, Mara, Aramini, Andrea, Degennaro, Leonardo, Luisi, Renzo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2018
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6644220/
https://www.ncbi.nlm.nih.gov/pubmed/31458153
http://dx.doi.org/10.1021/acsomega.8b02273
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author Colella, Marco
Musci, Pantaleo
Carlucci, Claudia
Lillini, Samuele
Tomassetti, Mara
Aramini, Andrea
Degennaro, Leonardo
Luisi, Renzo
author_facet Colella, Marco
Musci, Pantaleo
Carlucci, Claudia
Lillini, Samuele
Tomassetti, Mara
Aramini, Andrea
Degennaro, Leonardo
Luisi, Renzo
author_sort Colella, Marco
collection PubMed
description [Image: see text] We report herein a synthetic protocol for the preparation of 1,3-dibromo-1,1-difluoro-2-propanone, a new synthon used for the first time in a reaction with aromatic amines and sodium thiocyanate, leading to thiazoles which are useful candidates in drug discovery programs. The new synthon allows to introduce a bromodifluoromethyl group at the C4 of the thiazole, and it is amenable of further transformation such as the Br/F exchange useful in radiopharmaceutics. Application of the strategy to the preparation of a precursor of the biologically relevant DF2755Y is also reported.
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spelling pubmed-66442202019-08-27 1,3-Dibromo-1,1-difluoro-2-propanone as a Useful Synthon for a Chemoselective Preparation of 4-Bromodifluoromethyl Thiazoles Colella, Marco Musci, Pantaleo Carlucci, Claudia Lillini, Samuele Tomassetti, Mara Aramini, Andrea Degennaro, Leonardo Luisi, Renzo ACS Omega [Image: see text] We report herein a synthetic protocol for the preparation of 1,3-dibromo-1,1-difluoro-2-propanone, a new synthon used for the first time in a reaction with aromatic amines and sodium thiocyanate, leading to thiazoles which are useful candidates in drug discovery programs. The new synthon allows to introduce a bromodifluoromethyl group at the C4 of the thiazole, and it is amenable of further transformation such as the Br/F exchange useful in radiopharmaceutics. Application of the strategy to the preparation of a precursor of the biologically relevant DF2755Y is also reported. American Chemical Society 2018-11-05 /pmc/articles/PMC6644220/ /pubmed/31458153 http://dx.doi.org/10.1021/acsomega.8b02273 Text en Copyright © 2018 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Colella, Marco
Musci, Pantaleo
Carlucci, Claudia
Lillini, Samuele
Tomassetti, Mara
Aramini, Andrea
Degennaro, Leonardo
Luisi, Renzo
1,3-Dibromo-1,1-difluoro-2-propanone as a Useful Synthon for a Chemoselective Preparation of 4-Bromodifluoromethyl Thiazoles
title 1,3-Dibromo-1,1-difluoro-2-propanone as a Useful Synthon for a Chemoselective Preparation of 4-Bromodifluoromethyl Thiazoles
title_full 1,3-Dibromo-1,1-difluoro-2-propanone as a Useful Synthon for a Chemoselective Preparation of 4-Bromodifluoromethyl Thiazoles
title_fullStr 1,3-Dibromo-1,1-difluoro-2-propanone as a Useful Synthon for a Chemoselective Preparation of 4-Bromodifluoromethyl Thiazoles
title_full_unstemmed 1,3-Dibromo-1,1-difluoro-2-propanone as a Useful Synthon for a Chemoselective Preparation of 4-Bromodifluoromethyl Thiazoles
title_short 1,3-Dibromo-1,1-difluoro-2-propanone as a Useful Synthon for a Chemoselective Preparation of 4-Bromodifluoromethyl Thiazoles
title_sort 1,3-dibromo-1,1-difluoro-2-propanone as a useful synthon for a chemoselective preparation of 4-bromodifluoromethyl thiazoles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6644220/
https://www.ncbi.nlm.nih.gov/pubmed/31458153
http://dx.doi.org/10.1021/acsomega.8b02273
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