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 York
Ag3PW12O40: 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. -
1b
Landquist JK. In Comprehensive Heterocyclic Chemistry Vol. 1: Katritzky A. R., Rees C. W., Pergamon; Oxford: 1984. p.166-170 - 2
Randall LO.Kappel B. BenzodiazepinesGarattini S.Mussini E.Randall LO. Raven Press; New York: 1973. p.27 - 3
Haris RC, andStraley JM. inventors; U. S. Patent, 1537757. ; Chem. Abstr. 1970, 73, 100054w - 4
De Baun JR,Pallos FM, andBaker DR. inventors; U. S. Patent, 3978227. ; Chem. Abstr. 1977, 86, 5498d -
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