Tritylamine as an Ammonia Surrogate in the Ugi Reaction Provides Access to Unprecedented 5-Sulfamido Oxazoles Using Burgess-type Reagents

[Image: see text] Starting from a wide range of α-acylamino amide substructures synthesized using tritylamine as an ammonia surrogate in the Ugi reaction, Burgess-type reagents enable cyclodehydration and afford unprecedented oxazole scaffolds with four points of diversity, including a sulfamide moi...

Descripción completa

Detalles Bibliográficos
Autores principales: Bhela, Irene Preet, Serafini, Marta, Del Grosso, Erika, Tron, Gian Cesare, Pirali, Tracey
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8289289/
https://www.ncbi.nlm.nih.gov/pubmed/33913716
http://dx.doi.org/10.1021/acs.orglett.1c01002
_version_ 1783724272937598976
author Bhela, Irene Preet
Serafini, Marta
Del Grosso, Erika
Tron, Gian Cesare
Pirali, Tracey
author_facet Bhela, Irene Preet
Serafini, Marta
Del Grosso, Erika
Tron, Gian Cesare
Pirali, Tracey
author_sort Bhela, Irene Preet
collection PubMed
description [Image: see text] Starting from a wide range of α-acylamino amide substructures synthesized using tritylamine as an ammonia surrogate in the Ugi reaction, Burgess-type reagents enable cyclodehydration and afford unprecedented oxazole scaffolds with four points of diversity, including a sulfamide moiety in the 5-position. The synthetic procedure employs readily available starting materials and proceeds smoothly under mild reaction conditions with good tolerance for a variety of functional groups, coming to fill a gap in the field of oxazole compounds.
format Online
Article
Text
id pubmed-8289289
institution National Center for Biotechnology Information
language English
publishDate 2021
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-82892892021-07-20 Tritylamine as an Ammonia Surrogate in the Ugi Reaction Provides Access to Unprecedented 5-Sulfamido Oxazoles Using Burgess-type Reagents Bhela, Irene Preet Serafini, Marta Del Grosso, Erika Tron, Gian Cesare Pirali, Tracey Org Lett [Image: see text] Starting from a wide range of α-acylamino amide substructures synthesized using tritylamine as an ammonia surrogate in the Ugi reaction, Burgess-type reagents enable cyclodehydration and afford unprecedented oxazole scaffolds with four points of diversity, including a sulfamide moiety in the 5-position. The synthetic procedure employs readily available starting materials and proceeds smoothly under mild reaction conditions with good tolerance for a variety of functional groups, coming to fill a gap in the field of oxazole compounds. American Chemical Society 2021-04-29 2021-05-07 /pmc/articles/PMC8289289/ /pubmed/33913716 http://dx.doi.org/10.1021/acs.orglett.1c01002 Text en © 2021 The Authors. Published by American Chemical Society Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Bhela, Irene Preet
Serafini, Marta
Del Grosso, Erika
Tron, Gian Cesare
Pirali, Tracey
Tritylamine as an Ammonia Surrogate in the Ugi Reaction Provides Access to Unprecedented 5-Sulfamido Oxazoles Using Burgess-type Reagents
title Tritylamine as an Ammonia Surrogate in the Ugi Reaction Provides Access to Unprecedented 5-Sulfamido Oxazoles Using Burgess-type Reagents
title_full Tritylamine as an Ammonia Surrogate in the Ugi Reaction Provides Access to Unprecedented 5-Sulfamido Oxazoles Using Burgess-type Reagents
title_fullStr Tritylamine as an Ammonia Surrogate in the Ugi Reaction Provides Access to Unprecedented 5-Sulfamido Oxazoles Using Burgess-type Reagents
title_full_unstemmed Tritylamine as an Ammonia Surrogate in the Ugi Reaction Provides Access to Unprecedented 5-Sulfamido Oxazoles Using Burgess-type Reagents
title_short Tritylamine as an Ammonia Surrogate in the Ugi Reaction Provides Access to Unprecedented 5-Sulfamido Oxazoles Using Burgess-type Reagents
title_sort tritylamine as an ammonia surrogate in the ugi reaction provides access to unprecedented 5-sulfamido oxazoles using burgess-type reagents
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8289289/
https://www.ncbi.nlm.nih.gov/pubmed/33913716
http://dx.doi.org/10.1021/acs.orglett.1c01002
work_keys_str_mv AT bhelairenepreet tritylamineasanammoniasurrogateintheugireactionprovidesaccesstounprecedented5sulfamidooxazolesusingburgesstypereagents
AT serafinimarta tritylamineasanammoniasurrogateintheugireactionprovidesaccesstounprecedented5sulfamidooxazolesusingburgesstypereagents
AT delgrossoerika tritylamineasanammoniasurrogateintheugireactionprovidesaccesstounprecedented5sulfamidooxazolesusingburgesstypereagents
AT trongiancesare tritylamineasanammoniasurrogateintheugireactionprovidesaccesstounprecedented5sulfamidooxazolesusingburgesstypereagents
AT piralitracey tritylamineasanammoniasurrogateintheugireactionprovidesaccesstounprecedented5sulfamidooxazolesusingburgesstypereagents

Ejemplares similares