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 York2-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.259Reference Ris Wihthout Link
- 1b 
             
            Wipf P. Chem. Rev. 1995, 95: 2115Reference Ris Wihthout Link
- 1c 
             
            Jin Z. Nat. Prod. Rep. 2003, 20: 584Reference Ris Wihthout Link
- 1d 
             
            Oxazoles: Synthesis, Reactions, and Spectroscopy, Part
               A
              
            Vol. 60: 
             
            Palmer DC. Wiley; Hoboken NJ: 2003.Reference Ris Wihthout Link
- 2a 
             
            Oxazoles: Synthesis, Reactions, and
               Spectroscopy, Part B
              
            Vol.
            60: 
             
            Palmer DC. Wiley; Hoboken NJ: 2004.Reference Ris Wihthout Link
- 2b 
             
            Boyd GV. In Science of Synthesis Vol. 11:Schaumann E. Georg Thieme Verlag; Stuttgart: 2002. p.383Reference Ris Wihthout Link
- 2c 
             
            Hartner FW. In Comprehensive Heterocyclic Chemistry II Vol. 3:Katritzky AR.Rees CW.Scriven EFV. Elsevier; Oxford: 1996. p.261Reference Ris Wihthout Link
- 2d 
             
            Maryanoff BE. Chemistry of Heterocyclic Compounds Vol. 45:Turchi IJ. Wiley; Chichester: 1986. p.963Reference Ris Wihthout Link
- 2e 
             
            Turchi IJ.Dewar MJS. Chem. Rev. 1975, 75: 389Reference Ris Wihthout Link
- See, for example:
- 3a 
             
            Dalvie DK.Kalgutkar AS.Khojasteh-Bakht SC.Obach RS.O’Donnell JP. Chem. Res. Toxicol. 2002, 15: 269Reference Ris Wihthout Link
- 3b 
             
            McGovern SL.Caselli E.Grigorieff N.Shoichet BK. J. Med. Chem. 2002, 45: 1712Reference Ris Wihthout Link
- 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: 1031Reference Ris Wihthout Link
- 4a  
            For syntheses of oxazole containing macrocycles and their biological activity, see, for example, ref. 1b. Reference Ris Wihthout Link
- 4b  For a recent synthesis,
            see, for example:  
            Wipf P.Graham TH. J. Am. Chem. Soc. 2004, 126: 15346Reference Ris Wihthout Link
- 5a  
            Brown WK. inventors; US Patent 3574228. (John Wyeth & Brothers Ltd.); ; Chem. Abstr. 1969, 71, 124422Reference Ris Wihthout Link
- 5b  
            Meguro K, andFujita T. inventors; US Patent 4596816. (Takeda Chemical Ind.); ; Chem Abstr. 1984, 100, 121045Reference Ris Wihthout Link
- 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: 3604Reference Ris Wihthout Link
- 8b 
             
            Wipf P.Lim S. J. Am. Chem. Soc. 1995, 117: 558Reference Ris Wihthout Link
- 8c 
             
            Phillips AJ.Uto Y.Wipf P.Reno MJ.Williams DR. Org. Lett. 2000, 2: 1165Reference Ris Wihthout Link
- 8d 
             
            Wipf P.Methot J.-L. Org. Lett. 2001, 3: 1261Reference Ris Wihthout Link
- 9a 
             
            Wipf P.Rahman LT.Rector SR. J. Org. Chem. 1998, 63: 7132Reference Ris Wihthout Link
- 9b 
             
            Arcadi A.Cacchi S.Cascia L.Fabrizi G.Marinelli F. Org. Lett. 2001, 3: 2501Reference Ris Wihthout Link
- 9c 
             
            Coqueron P.-Y.Didier C.Ciufolini MA. Angew. Chem. Int. Ed. 2003, 42: 1411Reference Ris Wihthout Link
- 10 
             
            Hashmi ASK.Weyrauch JP.Frey W.Bats JW. Org. Lett. 2004, 6: 4391Reference Ris Wihthout Link
- For reviews, see:
- 11a 
             
            D’Souza DM.Müller TJJ. Chem. Soc. Rev. 2007, 36: 1095Reference Ris Wihthout Link
- 11b 
             
            Müller TJJ. Chim. Oggi/Chem. Today 2007, 25: 70Reference Ris Wihthout Link
- 11c 
             
            Müller TJJ. In Targets in Heterocyclic Systems: Chemistry and Properties Vol. 10:Attanasi OA.Spinelli D. Italian Society of Chemistry; Rome: 2006. p.54Reference Ris Wihthout Link
- 11d 
             
            Müller TJJ.D’Souza DM. Pure Appl. Chem. 2008, 80: 609Reference Ris Wihthout Link
- 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.Reference Ris Wihthout Link
 
    