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  2004(6): 901-904  
DOI: 10.1055/s-2004-816013
   DOI: 10.1055/s-2004-816013
PAPER
© Georg Thieme Verlag Stuttgart · New YorkAg3PW12O40: A Novel and Recyclable Heteropoly Acid for the Synthesis of 1,5-Benzodiazepines under Solvent-Free Conditions
Further Information
            
               
                  
                        
                              Received
                              16 December 2003 
                      
Publication Date:
15 March 2004 (online)
            
         
      
   Publication History
Publication Date:
15 March 2004 (online)

Abstract
o-Phenylenediamines undergo smooth condensation with ketones having hydrogens at α-position on the surface of heteropoly acid (Ag3PW12O40) under extremely mild conditions to afford the corresponding 1,5-benzodiazepines in excellent yields with high selectivity. The catalyst can be recovered by simple filteration and can be reused in subsequent reactions.
Keywords
heteropoly acids - o-phenylenediamines - ketones - benzodiazepines
- 1a 
             
            Schutz H. Benzodiazepines Springer; Heidelberg: 1982.Reference Ris Wihthout Link
- 1b 
             
            Landquist JK. In Comprehensive Heterocyclic Chemistry Vol. 1: Katritzky A. R., Rees C. W., Pergamon; Oxford: 1984. p.166-170Reference Ris Wihthout Link
- 2 
             
            Randall LO.Kappel B. BenzodiazepinesGarattini S.Mussini E.Randall LO. Raven Press; New York: 1973. p.27Reference Ris Wihthout Link
- 3  
            Haris RC, andStraley JM. inventors; U. S. Patent, 1537757. ; Chem. Abstr. 1970, 73, 100054wReference Ris Wihthout Link
- 4  
            De Baun JR,Pallos FM, andBaker DR. inventors; U. S. Patent, 3978227. ; Chem. Abstr. 1977, 86, 5498dReference Ris Wihthout Link
- 5a 
             
            Aversa MC.Ferlazzo A.Gionnetto P.Kohnke FH. Synthesis 1986, 230
- 5b 
             
            Chimirri A.Grasso S.Ottana R.Romeo G.Zappala M. J. Heterocycl. Chem. 1990, 27: 371
- 5c 
             
            Essaber M.Baouid A.Hasnaoui A.Benharref A.Lavergne JP. Synth. Commun. 1998, 28: 4097
- 5d 
             
            El-Sayed AM.Abdel-Ghany H.El-Saghier AMM. Synth. Commun. 1999, 29: 3561
- 6a 
             
            Herbert JAL.Suschitzky H. J. Chem. Soc., Perkin Trans 1 1974, 2657
- 6b 
             
            Kaupp G.Pogodda U.Schmeyers J. Chem. Ber. 1994, 127: 2249
- 6c 
             
            Balakrishna MS.Kaboudin B. Tetrahedron Lett. 2001, 42: 1127
- 6d 
             
            Curini M.Epifano F.Marcotullio MC.Rosati O. Tetrahedron Lett. 2001, 42: 3193
- 7a 
             
            Morales HR.Bulbarela A.Contreras R. Heterocycles 1986, 24: 135
- 7b 
             
            Pozarentzi M.Stephanatou JS.Tsoleridis CA. Tetrahedron Lett. 2002, 43: 1755
- 7c 
             
            Reddy BM.Sreekanth PM. Tetrahedron Lett. 2003, 44: 4447
- 7d 
             
            Jarikote DV.Siddiqui SA.Rajagopal R.Daniel T.Lahoti RJ.Srinivasan KV. Tetrahedron Lett. 2003, 44: 1835
- 8 
             
            Clark JH. Acc. Chem. Res. 2002, 35: 791
- 9a 
             
            Okuhara T.Mizuno N.Misono M. Applied Catalysis A: General 2001, 222: 63
- 9b 
             
            Kozhevnikov IV. Chem. Rev. 1998, 98: 171
- 10 Preparation of catalyst: 
            Haber J.Pamin K.Matachowski L.Napruszewska B.Poltowicz J. J. Catal. 2002, 207: 296
- 11 Solvent-free reactions: 
            Tanaka K.Toda F. Chem. Rev. 2000, 100: 1025
 
    