DMAP-Catalyzed Regel-Type Direct C-2 (Hetero)Aroylation of Oxazoles and Thiazoles Derivatives with Acid Chlorides

Pierrik Lassalas; Francis Marsais; Christophe Hoarau

doi:10.1055/s-0033-1339858

Synlett, Table of Contents

Synlett 2013; 24(17): 2233-2240
DOI: 10.1055/s-0033-1339858

letter

DMAP-Catalyzed Regel-Type Direct C-2 (Hetero)Aroylation of Oxazoles and Thiazoles Derivatives with Acid Chlorides

Pierrik Lassalas

Normandie Université, COBRA, UMR 6014 et FR 3038, Université de Rouen, INSA de Rouen, CNRS, 1 rue Tesnière, 76821 Mont-Saint-Aignan Cedex, France Fax: +33(235)522962 Email: christophe.hoarau@insa-rouen.fr

,

Francis Marsais

Normandie Université, COBRA, UMR 6014 et FR 3038, Université de Rouen, INSA de Rouen, CNRS, 1 rue Tesnière, 76821 Mont-Saint-Aignan Cedex, France Fax: +33(235)522962 Email: christophe.hoarau@insa-rouen.fr

,

Christophe Hoarau*

Normandie Université, COBRA, UMR 6014 et FR 3038, Université de Rouen, INSA de Rouen, CNRS, 1 rue Tesnière, 76821 Mont-Saint-Aignan Cedex, France Fax: +33(235)522962 Email: christophe.hoarau@insa-rouen.fr

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Abstract

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Abstract

A Regel-type transition-metal-free direct C-2 aroylation of (benzo)oxazoles, (benzo)thiazoles and 1,3,4-oxadiazoles with acid chlorides catalyzed by N,N-dimethyl-4-aminopyridine (DMAP) is described. This methodology is effective with several aroyl and heteroaroyl chlorides affording the corresponding 2-ketoazoles in moderate to excellent yields.

Key words

acylation - azoles - C–H functionalization - heterocycles - metal-free - regioselectivity

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References

References and Notes

1a Grimmett MR In Comprehensive Heterocyclic Chemistry II . Katritzky AR, Rees CW, Scriven EF. V. Pergamon; Oxford: 1996: 77-220
1b Myllymäki MJ, Saario SM, Kataja AO, Castillo-Melendez JA, Nevalainen T, Juvonen RO, Järvinen T, Koskinen AM. P. J. Med. Chem. 2007; 50: 4236
1c Janssens F, Leenaerts J, Diels G, De Boeck B, Megens A, Langlois X, van Rossem K, Beetens J, Borgers M. J. Med. Chem. 2005; 48: 2154
1d Lee J, Kim H, Yu H, Chung JY, Oh C.-H, Yoo KH, Sim T, Hah J.-M. Bioorg. Med. Chem. Lett. 2010; 20: 1573

2a Joule JA, Mills K. Heterocyclic Chemistry . John Wiley & Sons; New York: 2010. 5th ed., 763
2b Zificsak CA, Hlasta DJ. Tetrahedron 2004; 60: 8991
2c Alberico D, Scott ME, Lautens M. Chem. Rev. 2007; 107: 174

3a Dondoni A, Fantin G, Fogagnolo M, Medici A, Pedrini P. J. Org. Chem. 1987; 52: 3413
3b Harn NK, Gramer CJ, Anderson BA. Tetrahedron Lett. 1995; 36: 9453
3c Pippel DJ, Mapes CM, Mani NS. J. Org. Chem. 2007; 72: 5828
3d Rohbogner CJ, Wunderlich SH, Clososki GC, Knochel P. Eur. J. Org. Chem. 2009; 1781
3e Couture A, Grandclaudon P, Hoarau C, Cornet J, Hénichart J.-P, Houssin R. J. Org. Chem. 2002; 67: 3601

4a Bellina F, Rossi R. Adv. Synth. Catal. 2010; 352: 1223
4b Roger J, Gottumukkala AL, Doucet H. ChemCatChem 2010; 2: 20
4c McGlacken GP, Bateman LM. Chem. Soc. Rev. 2009; 38: 2447
4d Ackermann L, Vicente R, Kapdi AR. Angew. Chem. Int. Ed. 2009; 48: 9792
4e Campeau L.-C, Fagnou K. Chem. Soc. Rev. 2007; 36: 1058
4f Seregin IV, Gevorgyan V. Chem. Soc. Rev. 2007; 36: 1173

5 Wu X.-F, Anbarasan P, Neumann H, Beller M. Angew. Chem. Int. Ed. 2010; 49: 7316

6a Sun C.-L, Li H, Yu D.-G, Yu M, Zhou X, Lu X.-Y, Huang K, Zheng S.-F, Li B.-J, Shi Z.-J. Nat. Chem. 2010; 2: 1044
6b Popov I, Do H.-Q, Daugulis O. J. Org. Chem. 2009; 74: 8309
6c Shirakawa E, Itoh K.-I, Higashino T, Hayashi T. J. Am. Chem. Soc. 2010; 132: 15537
6d Vechorkin O, Hirt N, Hu X. Org. Lett. 2010; 12: 3567
6e Verrier C, Lassalas P, Théveau L, Quéguiner G, Trécourt F, Marsais F, Hoarau C. Beilstein J. Org. Chem. 2011; 7: 1584

7 Gao Q, Wu X, Jia F, Liu M, Zhu Y, Cai Q, Wu A. J. Org. Chem. 2013; 78: 2792

8a Regel E. Justus Liebigs Ann. Chem. 1977; 159
8b Regel E, Büchel K.-H. Justus Liebigs Ann. Chem. 1977; 145

9 Dondoni A, Fantin G, Fogagnolo M, Medici A, Pedrini P. J. Org. Chem. 1988; 53: 1748

10a Bull JA, Balskus EP, Horan RA. J, Langner M, Ley SV. Angew. Chem. Int. Ed. 2006; 45: 6714
10b Bull JA, Balskus EP, Horan RA. J, Langner M, Ley SV. Chem. Eur. J. 2007; 13: 5515
10c Mulder RJ, Shafer CM, Molinski TF. J. Org. Chem. 1999; 64: 4995
10d Searle PA, Richter RK, Molinski TF. J. Org. Chem. 1996; 61: 4073
10e Shioiri T, Chittari P, Hamada Y. Heterocycles 2003; 59: 465

11 Boga C, Stengel R, Abdayem R, Del Vecchio E, Forlani L, Todesco PE. J. Org. Chem. 2004; 69: 8903
12 Fan X, He Y, Zhang X, Guo S, Wang Y. Tetrahedron 2011; 67: 6369
13 Gemma S, Campiani G, Butini S, Kukreja G, Coccone SS, Joshi BP, Persico M, Nacci V, Fiorini I, Novellino E, Fattorusso E, Taglialatela-Scafati O, Savini L, Taramelli D, Basilico N, Parapini S, Morace G, Yardley V, Croft S, Coletta M, Marini S, Fattorusso C. J. Med. Chem. 2008; 51: 1278
14 Van Leusen AM, Hoogenboom BE, Siderius H. Tetrahedron Lett. 1972; 2369
15 Martin T, Verrier C, Hoarau C, Marsais F. Org. Lett. 2008; 10: 2909
16 Schröder R, Schöllkopf U, Blume E, Hoppe I. Liebigs Ann. Chem. 1975; 533
17 Kudelko A. Tetrahedron 2011; 67: 8502
18 Kawano T, Hirano K, Satoh T, Miura M. J. Am. Chem. Soc. 2010; 132: 6900

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