A CONVENIENT FORMATION OF HIGHLY FUNCTIONALIZED 5-BROMO-1,3-THIAZOLES.

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

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A CONVENIENT FORMATION OF HIGHLY FUNCTIONALIZED 5-BROMO-1,3-THIAZOLES Eduard Dolusic, Sara Modaffari, Johan Wouters, Bernard Masereel and Raphaël Frédérick NAmur MEDIcine Center (NAMEDIC), NARILIS, 61 rue de Bruxelles, 5000 Namur, Belgium In the framework of our research program, we were interested in the synthesis of substituted thiazole N-oxides. However, treatment of starting thiazoles with mCPBA1 did not afford the desired 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, hydrobromide salts. Oxidative bromination mediated by mCPBA then occurred in the 5-position of the thiazole ring. Various 5-bromo-1,3-thiazoles bearing alkyl and aryl substituents (containing both electron withdrawing and electron donating groups) in the 2- and 4-positions very easily prepared in this way. These products formed rapidly, in an one-pot operation from simple starting materials, using mild conditions (room temperature) and avoiding the use of catalysts or hazardous reagents like elemental bromine. This convenient procedure allows simple and quick access to a range of highly functionalized thiazoles, which can be further elaborated by known chemical methods. References: 1. e. g. Campeau, L.-C, et al, J. Am. Chem. Soc. 2009, 131, 3291-3306 ; Campeau, L.-C, et al, J. Am. Chem. Soc. 2008, 130, 3276-3277. This work is supported by the FNRS and the Walloon Region (BioWin project CANTOL: Convention n° 5678).
langue originaleAnglais
PagesBook of Abstracts, 15th Sigma-Aldrich Organic Synthesis Meeting, Spa, Belgium, 1-2 December 2011, p. 25
Nombre de pages1
étatPublié - 2011
Evénement15th SIGMA-ALDRICH Organic Synthesis Meeting - Spa, Belgique
Durée: 1 déc. 2011 → …

Une conférence

Une conférence15th SIGMA-ALDRICH Organic Synthesis Meeting
PaysBelgique
La villeSpa
période1/12/11 → …

Empreinte digitale

Thiazoles
Bearings (structural)
Bromine
Electrons
Oxides
Medicine
Salts
Catalysts

Citer ceci

Dolusic, E., Modaffari, S., Wouters, J., Masereel, B., & Frédérick, R. (2011). A CONVENIENT FORMATION OF HIGHLY FUNCTIONALIZED 5-BROMO-1,3-THIAZOLES.. Book of Abstracts, 15th Sigma-Aldrich Organic Synthesis Meeting, Spa, Belgium, 1-2 December 2011, p. 25. Poster présenté � 15th SIGMA-ALDRICH Organic Synthesis Meeting, Spa, Belgique.
@conference{ff4366e316794d2f846a237ee59a8efb,
title = "A CONVENIENT FORMATION OF HIGHLY FUNCTIONALIZED 5-BROMO-1,3-THIAZOLES.",
abstract = "A CONVENIENT FORMATION OF HIGHLY FUNCTIONALIZED 5-BROMO-1,3-THIAZOLES Eduard Dolusic, Sara Modaffari, Johan Wouters, Bernard Masereel and Rapha{\"e}l Fr{\'e}d{\'e}rick NAmur MEDIcine Center (NAMEDIC), NARILIS, 61 rue de Bruxelles, 5000 Namur, Belgium In the framework of our research program, we were interested in the synthesis of substituted thiazole N-oxides. However, treatment of starting thiazoles with mCPBA1 did not afford the desired 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, hydrobromide salts. Oxidative bromination mediated by mCPBA then occurred in the 5-position of the thiazole ring. Various 5-bromo-1,3-thiazoles bearing alkyl and aryl substituents (containing both electron withdrawing and electron donating groups) in the 2- and 4-positions very easily prepared in this way. These products formed rapidly, in an one-pot operation from simple starting materials, using mild conditions (room temperature) and avoiding the use of catalysts or hazardous reagents like elemental bromine. This convenient procedure allows simple and quick access to a range of highly functionalized thiazoles, which can be further elaborated by known chemical methods. References: 1. e. g. Campeau, L.-C, et al, J. Am. Chem. Soc. 2009, 131, 3291-3306 ; Campeau, L.-C, et al, J. Am. Chem. Soc. 2008, 130, 3276-3277. This work is supported by the FNRS and the Walloon Region (BioWin project CANTOL: Convention n° 5678).",
author = "Eduard Dolusic and Sara Modaffari and Johan Wouters and Bernard Masereel and Rapha{\"e}l Fr{\'e}d{\'e}rick",
year = "2011",
language = "English",
pages = "Book of Abstracts, 15th Sigma--Aldrich Organic Synthesis Meeting, Spa, Belgium, 1--2 December 2011, p. 25",
note = "15th SIGMA-ALDRICH Organic Synthesis Meeting ; Conference date: 01-12-2011",

}

Dolusic, E, Modaffari, S, Wouters, J, Masereel, B & Frédérick, R 2011, 'A CONVENIENT FORMATION OF HIGHLY FUNCTIONALIZED 5-BROMO-1,3-THIAZOLES.', 15th SIGMA-ALDRICH Organic Synthesis Meeting, Spa, Belgique, 1/12/11 p. Book of Abstracts, 15th Sigma-Aldrich Organic Synthesis Meeting, Spa, Belgium, 1-2 December 2011, p. 25.

A CONVENIENT FORMATION OF HIGHLY FUNCTIONALIZED 5-BROMO-1,3-THIAZOLES. / Dolusic, Eduard; Modaffari, Sara; Wouters, Johan; Masereel, Bernard; Frédérick, Raphaël.

2011. Book of Abstracts, 15th Sigma-Aldrich Organic Synthesis Meeting, Spa, Belgium, 1-2 December 2011, p. 25 Poster présenté � 15th SIGMA-ALDRICH Organic Synthesis Meeting, Spa, Belgique.

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

TY - CONF

T1 - A CONVENIENT FORMATION OF HIGHLY FUNCTIONALIZED 5-BROMO-1,3-THIAZOLES.

AU - Dolusic, Eduard

AU - Modaffari, Sara

AU - Wouters, Johan

AU - Masereel, Bernard

AU - Frédérick, Raphaël

PY - 2011

Y1 - 2011

N2 - A CONVENIENT FORMATION OF HIGHLY FUNCTIONALIZED 5-BROMO-1,3-THIAZOLES Eduard Dolusic, Sara Modaffari, Johan Wouters, Bernard Masereel and Raphaël Frédérick NAmur MEDIcine Center (NAMEDIC), NARILIS, 61 rue de Bruxelles, 5000 Namur, Belgium In the framework of our research program, we were interested in the synthesis of substituted thiazole N-oxides. However, treatment of starting thiazoles with mCPBA1 did not afford the desired 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, hydrobromide salts. Oxidative bromination mediated by mCPBA then occurred in the 5-position of the thiazole ring. Various 5-bromo-1,3-thiazoles bearing alkyl and aryl substituents (containing both electron withdrawing and electron donating groups) in the 2- and 4-positions very easily prepared in this way. These products formed rapidly, in an one-pot operation from simple starting materials, using mild conditions (room temperature) and avoiding the use of catalysts or hazardous reagents like elemental bromine. This convenient procedure allows simple and quick access to a range of highly functionalized thiazoles, which can be further elaborated by known chemical methods. References: 1. e. g. Campeau, L.-C, et al, J. Am. Chem. Soc. 2009, 131, 3291-3306 ; Campeau, L.-C, et al, J. Am. Chem. Soc. 2008, 130, 3276-3277. This work is supported by the FNRS and the Walloon Region (BioWin project CANTOL: Convention n° 5678).

AB - A CONVENIENT FORMATION OF HIGHLY FUNCTIONALIZED 5-BROMO-1,3-THIAZOLES Eduard Dolusic, Sara Modaffari, Johan Wouters, Bernard Masereel and Raphaël Frédérick NAmur MEDIcine Center (NAMEDIC), NARILIS, 61 rue de Bruxelles, 5000 Namur, Belgium In the framework of our research program, we were interested in the synthesis of substituted thiazole N-oxides. However, treatment of starting thiazoles with mCPBA1 did not afford the desired 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, hydrobromide salts. Oxidative bromination mediated by mCPBA then occurred in the 5-position of the thiazole ring. Various 5-bromo-1,3-thiazoles bearing alkyl and aryl substituents (containing both electron withdrawing and electron donating groups) in the 2- and 4-positions very easily prepared in this way. These products formed rapidly, in an one-pot operation from simple starting materials, using mild conditions (room temperature) and avoiding the use of catalysts or hazardous reagents like elemental bromine. This convenient procedure allows simple and quick access to a range of highly functionalized thiazoles, which can be further elaborated by known chemical methods. References: 1. e. g. Campeau, L.-C, et al, J. Am. Chem. Soc. 2009, 131, 3291-3306 ; Campeau, L.-C, et al, J. Am. Chem. Soc. 2008, 130, 3276-3277. This work is supported by the FNRS and the Walloon Region (BioWin project CANTOL: Convention n° 5678).

M3 - Poster

SP - Book of Abstracts, 15th Sigma-Aldrich Organic Synthesis Meeting, Spa, Belgium, 1-2 December 2011, p. 25

ER -

Dolusic E, Modaffari S, Wouters J, Masereel B, Frédérick R. A CONVENIENT FORMATION OF HIGHLY FUNCTIONALIZED 5-BROMO-1,3-THIAZOLES.. 2011. Poster présenté � 15th SIGMA-ALDRICH Organic Synthesis Meeting, Spa, Belgique.