Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2009(3): 502-507
DOI: 10.1055/s-0028-1083294
DOI: 10.1055/s-0028-1083294
PSP
© Georg Thieme Verlag
Stuttgart ˙ New York
2-Oxazol-5-ylethanones by Consecutive Three-Component Amidation-Coupling-Cycloisomerization (ACCI) Sequence
Further Information
Received
4 September 2008
Publication Date:
19 December 2008 (online)
Publication History
Publication Date:
19 December 2008 (online)
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
-
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, andFujita 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.