Convenient one-pot formation of highly functionalized 5-halothiazoles

Eduard Dolusic, Sara Modaffari, Lionel Pochet, Johan Wouters, Bernard Masereel, Raphael Frédérick

Résultats de recherche: Contribution à un événement scientifique (non publié)Poster

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Résumé

Attempts to synthesize substituted thiazole N-oxides by treatment of 1,3-thiazoles with mCPBA(1,2) did not afford the expected products. Spectral analyses proved that corresponding 5-bromothiazoles were formed instead in very good yields. This can be explained by the fact that the starting compounds were, in fact, obtained as hydrobromide salts. Oxidative bromination mediated by mCPBA then occurred in the 5-position of the thiazole ring. Highly functionalized 5-bromo-2-amino-1,3-thiazoles bearing various substituents in the 4-position and on the 2-nitrogen could be easily prepared by this rapid and efficient one-pot method, using simple starting materials and mild conditions while avoiding the use of metal catalysts or hazardous reagents like elemental bromine. A number of oxidants, solvents and reaction conditions were next studied. The synthesis scope was successfully extended to 5-chlorothiazoles. Attempts were undertaken to further elaborate the 5-halothiazoles to pharmacologically interesting compounds.1. Campeau, L.-C. et al; J. Am. Chem. Soc. 2009, 131, 3291-3306. 2. Campeau, L.-C. et al; J. Am. Chem. Soc. 2008, 130, 3276-3277. This work is supported by the Belgian Fonds National pour la Recherche Scientifique (FNRS) and the Walloon Region (BioWin project CANTOL: Convention n° 5678).
langue originaleAnglais
PagesBook of Abstracts, Balticum Organicum Syntheticum, July 1-4 2012, Tallinn, Estonia, PO27, p. 74
Nombre de pages1
étatPublié - 1 juil. 2012
EvénementBalticum Organicum Syntheticum 2012 - Tallinn, Estonie
Durée: 1 juil. 20124 juil. 2012

Une conférence

Une conférenceBalticum Organicum Syntheticum 2012
PaysEstonie
La villeTallinn
période1/07/124/07/12

Empreinte digitale

Thiazoles
Bearings (structural)
Bromine
Oxidants
Oxides
Nitrogen
Salts
Metals
Catalysts

Citer ceci

Dolusic, E., Modaffari, S., Pochet, L., Wouters, J., Masereel, B., & Frédérick, R. (2012). Convenient one-pot formation of highly functionalized 5-halothiazoles. Book of Abstracts, Balticum Organicum Syntheticum, July 1-4 2012, Tallinn, Estonia, PO27, p. 74. Poster présenté � Balticum Organicum Syntheticum 2012, Tallinn, Estonie.
Dolusic, Eduard ; Modaffari, Sara ; Pochet, Lionel ; Wouters, Johan ; Masereel, Bernard ; Frédérick, Raphael. / Convenient one-pot formation of highly functionalized 5-halothiazoles. Poster présenté � Balticum Organicum Syntheticum 2012, Tallinn, Estonie.1 p.
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title = "Convenient one-pot formation of highly functionalized 5-halothiazoles",
abstract = "Attempts to synthesize substituted thiazole N-oxides by treatment of 1,3-thiazoles with mCPBA(1,2) did not afford the expected products. Spectral analyses proved that corresponding 5-bromothiazoles were formed instead in very good yields. This can be explained by the fact that the starting compounds were, in fact, obtained as hydrobromide salts. Oxidative bromination mediated by mCPBA then occurred in the 5-position of the thiazole ring. Highly functionalized 5-bromo-2-amino-1,3-thiazoles bearing various substituents in the 4-position and on the 2-nitrogen could be easily prepared by this rapid and efficient one-pot method, using simple starting materials and mild conditions while avoiding the use of metal catalysts or hazardous reagents like elemental bromine. A number of oxidants, solvents and reaction conditions were next studied. The synthesis scope was successfully extended to 5-chlorothiazoles. Attempts were undertaken to further elaborate the 5-halothiazoles to pharmacologically interesting compounds.1. Campeau, L.-C. et al; J. Am. Chem. Soc. 2009, 131, 3291-3306. 2. Campeau, L.-C. et al; J. Am. Chem. Soc. 2008, 130, 3276-3277. This work is supported by the Belgian Fonds National pour la Recherche Scientifique (FNRS) and the Walloon Region (BioWin project CANTOL: Convention n° 5678).",
author = "Eduard Dolusic and Sara Modaffari and Lionel Pochet and Johan Wouters and Bernard Masereel and Raphael Fr{\'e}d{\'e}rick",
year = "2012",
month = "7",
day = "1",
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pages = "Book of Abstracts, Balticum Organicum Syntheticum, July 1--4 2012, Tallinn, Estonia, PO27, p. 74",
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Dolusic, E, Modaffari, S, Pochet, L, Wouters, J, Masereel, B & Frédérick, R 2012, 'Convenient one-pot formation of highly functionalized 5-halothiazoles', Balticum Organicum Syntheticum 2012, Tallinn, Estonie, 1/07/12 - 4/07/12 p. Book of Abstracts, Balticum Organicum Syntheticum, July 1-4 2012, Tallinn, Estonia, PO27, p. 74.

Convenient one-pot formation of highly functionalized 5-halothiazoles. / Dolusic, Eduard; Modaffari, Sara; Pochet, Lionel; Wouters, Johan; Masereel, Bernard; Frédérick, Raphael.

2012. Book of Abstracts, Balticum Organicum Syntheticum, July 1-4 2012, Tallinn, Estonia, PO27, p. 74 Poster présenté � Balticum Organicum Syntheticum 2012, Tallinn, Estonie.

Résultats de recherche: Contribution à un événement scientifique (non publié)Poster

TY - CONF

T1 - Convenient one-pot formation of highly functionalized 5-halothiazoles

AU - Dolusic, Eduard

AU - Modaffari, Sara

AU - Pochet, Lionel

AU - Wouters, Johan

AU - Masereel, Bernard

AU - Frédérick, Raphael

PY - 2012/7/1

Y1 - 2012/7/1

N2 - Attempts to synthesize substituted thiazole N-oxides by treatment of 1,3-thiazoles with mCPBA(1,2) did not afford the expected products. Spectral analyses proved that corresponding 5-bromothiazoles were formed instead in very good yields. This can be explained by the fact that the starting compounds were, in fact, obtained as hydrobromide salts. Oxidative bromination mediated by mCPBA then occurred in the 5-position of the thiazole ring. Highly functionalized 5-bromo-2-amino-1,3-thiazoles bearing various substituents in the 4-position and on the 2-nitrogen could be easily prepared by this rapid and efficient one-pot method, using simple starting materials and mild conditions while avoiding the use of metal catalysts or hazardous reagents like elemental bromine. A number of oxidants, solvents and reaction conditions were next studied. The synthesis scope was successfully extended to 5-chlorothiazoles. Attempts were undertaken to further elaborate the 5-halothiazoles to pharmacologically interesting compounds.1. Campeau, L.-C. et al; J. Am. Chem. Soc. 2009, 131, 3291-3306. 2. Campeau, L.-C. et al; J. Am. Chem. Soc. 2008, 130, 3276-3277. This work is supported by the Belgian Fonds National pour la Recherche Scientifique (FNRS) and the Walloon Region (BioWin project CANTOL: Convention n° 5678).

AB - Attempts to synthesize substituted thiazole N-oxides by treatment of 1,3-thiazoles with mCPBA(1,2) did not afford the expected products. Spectral analyses proved that corresponding 5-bromothiazoles were formed instead in very good yields. This can be explained by the fact that the starting compounds were, in fact, obtained as hydrobromide salts. Oxidative bromination mediated by mCPBA then occurred in the 5-position of the thiazole ring. Highly functionalized 5-bromo-2-amino-1,3-thiazoles bearing various substituents in the 4-position and on the 2-nitrogen could be easily prepared by this rapid and efficient one-pot method, using simple starting materials and mild conditions while avoiding the use of metal catalysts or hazardous reagents like elemental bromine. A number of oxidants, solvents and reaction conditions were next studied. The synthesis scope was successfully extended to 5-chlorothiazoles. Attempts were undertaken to further elaborate the 5-halothiazoles to pharmacologically interesting compounds.1. Campeau, L.-C. et al; J. Am. Chem. Soc. 2009, 131, 3291-3306. 2. Campeau, L.-C. et al; J. Am. Chem. Soc. 2008, 130, 3276-3277. This work is supported by the Belgian Fonds National pour la Recherche Scientifique (FNRS) and the Walloon Region (BioWin project CANTOL: Convention n° 5678).

M3 - Poster

SP - Book of Abstracts, Balticum Organicum Syntheticum, July 1-4 2012, Tallinn, Estonia, PO27, p. 74

ER -

Dolusic E, Modaffari S, Pochet L, Wouters J, Masereel B, Frédérick R. Convenient one-pot formation of highly functionalized 5-halothiazoles. 2012. Poster présenté � Balticum Organicum Syntheticum 2012, Tallinn, Estonie.