A Facile, One-Pot Procedure for Forming Diarylimines from Nitroarenes and Benzaldehydes

Andrew L. Korich; Thomas S. Hughes

doi:10.1055/s-2007-986668

LETTER

A Facile, One-Pot Procedure for Forming Diarylimines from Nitroarenes and Benzaldehydes

Andrew L. Korich, Thomas S. Hughes*
Chemistry Department, Cook Physical Science Building, University of Vermont, 82 University Place, Burlington, VT 05405, USA
Fax: +1(802)6568705; e-Mail: Thomas.S.Hughes@uvm.edu;

Abstract

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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

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References

<A NAME="RS02607ST-1">1</A> Akazome M. Kondo T. Watanabe Y. J. Org. Chem. 1994, 59: 3375

<A NAME="RS02607ST-2A">2a</A> Gimenez R. Oriol L. Pinol M. Serrano JL. Vinuales AI. Fisher T. Stumpe J. Helv. Chim. Acta 2006, 89: 304

<A NAME="RS02607ST-2B">2b</A> Hari A. Karan C. Rodrigues WC. Miller BL. J. Org. Chem. 2001, 66: 991

<A NAME="RS02607ST-3">3</A> Nonkunsarn P. Ramsden C. Tetrahedron 1997, 53: 3805

<A NAME="RS02607ST-4">4</A> Neuvonen H. Neuvonen K. Fülöp F. J. Chem. Soc. 2006, 71: 3141

<A NAME="RS02607ST-5A">5a</A> Higuchi M. Tsuruta M. Chiba H. Shiki S. Yamamoto K. J. Am. Chem. Soc. 2003, 125: 9988

<A NAME="RS02607ST-5B">5b</A> Higuchi M. Shomura R. Ohtsuka Y. Hayashi A. Yamamoto K. Kurth DG. Org. Lett. 2006, 8: 4723

<A NAME="RS02607ST-5C">5c</A> Borisova NE. Reshetova MD. Ustynyuk YA. Chem. Rev. 2007, 107: 46

<A NAME="RS02607ST-6A">6a</A> Iqbal AF. J. Org. Chem. 1972, 37: 2791

<A NAME="RS02607ST-6B">6b</A> Macho V. Králik M. Hudec J. Cingelova J. J. Mol. Catal. A: Chem. 2004, 209: 69

<A NAME="RS02607ST-7A">7a</A> Mendenhall D. Smith PAS. Org. Synth., Coll. Vol. V 1979, 829

<A NAME="RS02607ST-7B">7b</A> Sundberg RJ. Pitts WJ. J. Org. Chem. 1991, 56: 3048

<A NAME="RS02607ST-7C">7c</A> Doxsee KM. Feigel M. Stewart KD. Canary JW. Knobler CD. Cram DJ. J. Am. Chem. Soc. 1987, 109: 3098

<A NAME="RS02607ST-7D">7d</A> Saramh P. Barua N. Tetrahedron Lett. 1990, 31: 4065

<A NAME="RS02607ST-8A">8a</A> Wang L. Li P. Wu Z. Yan J. Wang M. Ding Y. Synthesis 2003, 2001

<A NAME="RS02607ST-8B">8b</A> Fox BA. Threlfall TL. Org. Synth., Coll. Vol. V 1973, 346

<A NAME="RS02607ST-9A">9a</A> Merlic CG. Motamed S. Quinn B. J. Chem. Soc. 1995, 60: 3365

<A NAME="RS02607ST-9B">9b</A> 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:

<A NAME="RS02607ST-10A">10a</A> Bolognese A. Diurno AV. Mazzoni O. Giordano F. Tetrahedron 1997, 47: 1991

<A NAME="RS02607ST-10B">10b</A> For entry 5, see: Tabei K. Saitou E. Bull. Chem. Soc. Jpn. 1969, 42: 1440

<A NAME="RS02607ST-10C">10c</A> For entry 6, see: Marshall RL. Muderawan IW. Young DJ. J. Chem. Soc., Perkin Trans. 2 2000, 957

<A NAME="RS02607ST-10D">10d</A> For entry 10, see: Afarinkia KJ. Rees CW. Tetrahedron 1997, 46: 7175

<A NAME="RS02607ST-11">11</A> Milazzo G. Caroli S. Table of Standard Electrode Potentials John Wiley and Sons; New York: 1978.