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Synlett 2007(16): 2602-2604
DOI: 10.1055/s-2007-986668
DOI: 10.1055/s-2007-986668
LETTER
© Georg Thieme Verlag Stuttgart · New York
A Facile, One-Pot Procedure for Forming Diarylimines from Nitroarenes and Benzaldehydes
Further Information
Received
30 April 2007
Publication Date:
12 September 2007 (online)
Publication History
Publication Date:
12 September 2007 (online)
Abstract
An intermolecular reductive Schiff base formation from nitroarenes and benzaldehydes to yield diarylimines is carried out in the presence of iron powder and dilute acid. This process is tolerant of an array of functional groups and often proceeds quantitatively with no need for purification.
Key words
condensation - imine - Schiff bases - iron - green chemistry
- 1
Akazome M.Kondo T.Watanabe Y. J. Org. Chem. 1994, 59: 3375 -
2a
Gimenez R.Oriol L.Pinol M.Serrano JL.Vinuales AI.Fisher T.Stumpe J. Helv. Chim. Acta 2006, 89: 304 -
2b
Hari A.Karan C.Rodrigues WC.Miller BL. J. Org. Chem. 2001, 66: 991 - 3
Nonkunsarn P.Ramsden C. Tetrahedron 1997, 53: 3805 - 4
Neuvonen H.Neuvonen K.Fülöp F. J. Chem. Soc. 2006, 71: 3141 -
5a
Higuchi M.Tsuruta M.Chiba H.Shiki S.Yamamoto K. J. Am. Chem. Soc. 2003, 125: 9988 -
5b
Higuchi M.Shomura R.Ohtsuka Y.Hayashi A.Yamamoto K.Kurth DG. Org. Lett. 2006, 8: 4723 -
5c
Borisova NE.Reshetova MD.Ustynyuk YA. Chem. Rev. 2007, 107: 46 -
6a
Iqbal AF. J. Org. Chem. 1972, 37: 2791 -
6b
Macho V.Králik M.Hudec J.Cingelova J. J. Mol. Catal. A: Chem. 2004, 209: 69 -
7a
Mendenhall D.Smith PAS. Org. Synth., Coll. Vol. V 1979, 829 -
7b
Sundberg RJ.Pitts WJ. J. Org. Chem. 1991, 56: 3048 -
7c
Doxsee KM.Feigel M.Stewart KD.Canary JW.Knobler CD.Cram DJ. J. Am. Chem. Soc. 1987, 109: 3098 -
7d
Saramh P.Barua N. Tetrahedron Lett. 1990, 31: 4065 -
8a
Wang L.Li P.Wu Z.Yan J.Wang M.Ding Y. Synthesis 2003, 2001 -
8b
Fox BA.Threlfall TL. Org. Synth., Coll. Vol. V 1973, 346 -
9a
Merlic CG.Motamed S.Quinn B. J. Chem. Soc. 1995, 60: 3365 -
9b
Stefancich G.Artico M.Massa S.Corelli F. Synthesis 1981, 321 - For spectroscopic data on entries 1, 3, 4, 7-9, see ref. 3, for entry 2, see:
-
10a
Bolognese A.Diurno AV.Mazzoni O.Giordano F. Tetrahedron 1997, 47: 1991 -
10b For entry 5, see:
Tabei K.Saitou E. Bull. Chem. Soc. Jpn. 1969, 42: 1440 -
10c For entry 6, see:
Marshall RL.Muderawan IW.Young DJ. J. Chem. Soc., Perkin Trans. 2 2000, 957 -
10d For entry 10, see:
Afarinkia KJ.Rees CW. Tetrahedron 1997, 46: 7175 - 11
Milazzo G.Caroli S. Table of Standard Electrode Potentials John Wiley and Sons; New York: 1978.