2-Oxazol-5-ylethanones by Consecutive
Three-Component Amidation-Coupling-Cycloisomerization
(ACCI) Sequence

Eugen Merkul; Oliver Grotkopp; Thomas J. J. Müller

doi:10.1055/s-0028-1083294

PSP

2-Oxazol-5-ylethanones by Consecutive Three-Component Amidation-Coupling-Cycloisomerization (ACCI) Sequence

Eugen Merkul, Oliver Grotkopp, Thomas J. J. Müller*
Lehrstuhl für Organische Chemie, Institut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstraße 1, 40225 Düsseldorf, Germany
Fax: +49(211)8114324; e-Mail: ThomasJJ.Mueller@uni-duesseldorf.de;

Abstract

Alle Artikel dieser Rubrik

Abstract

Substituted oxazol-5-ylethanones can be synthesized in a consecutive three-component sequence starting from propargylamine and various acid chlorides, both for amidation and cross-coupling. Therefore, this diversity-oriented one-pot approach to substituted oxazoles can be considered as an amidation-coupling-cycloisomerization (ACCI) sequence.

Key words

C-C coupling - catalysis - cycloisomerization - multi-component reactions - oxazoles

Volltext

Referenzen

References

1a Jacobs HM. Burke BA. In Alkaloids Vol. 35: Brossi A. Academic Press; New York: 1989. p.259

1b Wipf P. Chem. Rev. 1995, 95: 2115

1c Jin Z. Nat. Prod. Rep. 2003, 20: 584

1d Oxazoles: Synthesis, Reactions, and Spectroscopy, Part A Vol. 60: Palmer DC. Wiley; Hoboken NJ: 2003.

2a Oxazoles: Synthesis, Reactions, and Spectroscopy, Part B Vol. 60: Palmer DC. Wiley; Hoboken NJ: 2004.

2b Boyd GV. In Science of Synthesis Vol. 11: Schaumann E. Georg Thieme Verlag; Stuttgart: 2002. p.383

2c Hartner FW. In Comprehensive Heterocyclic Chemistry II Vol. 3: Katritzky AR. Rees CW. Scriven EFV. Elsevier; Oxford: 1996. p.261

2d Maryanoff BE. Chemistry of Heterocyclic Compounds Vol. 45: Turchi IJ. Wiley; Chichester: 1986. p.963

2e Turchi IJ. Dewar MJS. Chem. Rev. 1975, 75: 389

See, for example:

3a Dalvie DK. Kalgutkar AS. Khojasteh-Bakht SC. Obach RS. O’Donnell JP. Chem. Res. Toxicol. 2002, 15: 269

3b McGovern SL. Caselli E. Grigorieff N. Shoichet BK. J. Med. Chem. 2002, 45: 1712

3c Murcia-Soler M. Perez-Gimenez F. Garcia-March FJ. Salabert-Salvador MT. Diaz-Villanueva W. Castro-Bleda MJ. Villanueva-Pareja A. J. Chem. Inf. Comput. Sci. 2004, 44: 1031

4a

For syntheses of oxazole containing macrocycles and their biological activity, see, for example, ref. 1b.

4b For a recent synthesis, see, for example: Wipf P. Graham TH. J. Am. Chem. Soc. 2004, 126: 15346

5a Brown WK. inventors; US Patent 3574228. (John Wyeth & Brothers Ltd.); ; Chem. Abstr. 1969, 71, 124422

5b Meguro K, and Fujita T. inventors; US Patent 4596816. (Takeda Chemical Ind.); ; Chem Abstr. 1984, 100, 121045

6 Wasserman HH. Vinick FJ. J. Org. Chem. 1973, 38: 2407

7 Dow RL. J. Org. Chem. 1990, 55: 386

8a Wipf P. Miller CP. J. Org. Chem. 1993, 58: 3604

8b Wipf P. Lim S. J. Am. Chem. Soc. 1995, 117: 558

8c Phillips AJ. Uto Y. Wipf P. Reno MJ. Williams DR. Org. Lett. 2000, 2: 1165

8d Wipf P. Methot J.-L. Org. Lett. 2001, 3: 1261

9a Wipf P. Rahman LT. Rector SR. J. Org. Chem. 1998, 63: 7132

9b Arcadi A. Cacchi S. Cascia L. Fabrizi G. Marinelli F. Org. Lett. 2001, 3: 2501

9c Coqueron P.-Y. Didier C. Ciufolini MA. Angew. Chem. Int. Ed. 2003, 42: 1411

10 Hashmi ASK. Weyrauch JP. Frey W. Bats JW. Org. Lett. 2004, 6: 4391

For reviews, see:

11a D’Souza DM. Müller TJJ. Chem. Soc. Rev. 2007, 36: 1095

11b Müller TJJ. Chim. Oggi/Chem. Today 2007, 25: 70

11c Müller TJJ. In Targets in Heterocyclic Systems: Chemistry and Properties Vol. 10: Attanasi OA. Spinelli D. Italian Society of Chemistry; Rome: 2006. p.54

11d Müller TJJ. D’Souza DM. Pure Appl. Chem. 2008, 80: 609

12 Merkul E. Müller TJJ. Chem. Commun. 2006, 4817

13 Wipf P. Aoyama Y. Benedum TE. Org. Lett. 2004, 6: 3593

14 Becker HGO. Beckert R. Domschke G. Fanghänel E. Habicher WD. Metz P. Pavel D. Schwetlick K. Organikum 21st ed.: Wiley-VCH; Weinheim: 2001.