Reductive coupling of nitroarenes to hydrazoarenes with aluminium and potassium hydroxide in methanol

Abstract

A simple and inexpensive procedure for the reductive coupling of nitroarenes to hydrazoarenes with aluminium and potassium hydroxide in methanol at ambient temperature is reported. The coupling is proposed to proceed by single electron transfer from aluminium.

References

1. (a) J. March, Advanced Organic Chemistry, 4th edn., J. Wiley & Sons, New York, 1992, p. 1216 and references cited therein; (b) H. O. House, Modern Synthetic Reactions, 2nd edn., W. A. Benjamin, Inc., Menlo Park, California, 1972, p. 175 and references cited therein; (c) H. Alper and M. Gopal, J. Chem. Soc., Chem. Commun., 1980, 821; (d) G. Theodoridis, M. C. Manfredi and J. D. Kreks, Tetrahedron Lett., 1990, 6141; (e) P. Sharmah and N. C. Barua, Tetrahedron Lett., 1990, 4065; (f) K. Makkanti, Y. V. Subba Rao and B. M. Chaudary, Tetrahedron Lett., 1989, 251; (g) S. Murata, M. Miura and M. Nomura, J. Chem. Soc., Perkin Trans. 2, 1989, 617; (h) A. Nose and T. Kudo, Chem. Pharm. Bull., 1991, 38, 2097; (i) A. S. Kende and J. S. Mendoza, Tetrahedron Lett., 1991, 1699; (j) M. Takeshita and S. Yoshida, Heterocycles, 1990, 31, 2201.
2. (a) Ref. 1(a), p. 1232; (b) A. Osuka, H. Shimizu and S. Suzuki, Chem. Lett., 1983, 1373; (c) T. Satoh, S. Suzuki, T. Kikuchi and T. Okada, Chem. Ind. (London), 1970, 1626; (d) H. N. Borah, D. Prajapati, J. S. Sandhu and A. C. Ghosh, Tetrahedron Lett., 1994, 3167; (e) S. R. Sandler and W. Karo, Organic Functional Group Preparations, vol. 2, Academic Press Inc., New York, 1971, p. 410; (f) H. Z. Huang, C. Chen, F. Zhu and Y. Liao, J. Organomet. Chem., 1989, 378, 147; (g) R. M. Moriarty, T. E. Hopkins, I. Prakash, B. K. Vaid and R. K. Vaid, Synth. Commun., 1990, 2353; (h) M. Prato, U. Quintily, L. Scapol and G. Scorrano, Bull. Soc. Chim. Fr., 1987, 99; (i) K. Ohe, S. Uemura, N. Sugita, H. Masuda and T. Taga, J. Org. Chem., 1989, 54, 4169; (j) Z. Hou, F. Fujiwara and H. Taniguchi, J. Org. Chem., 1988, 53, 3118; (k) T. H. You, M. K. Park and B. H. Ham, J. Chem. Res. (S), 1992, 336.
3. (a) For a review see ref. 2(e), p. 313; (b) R. O. Hutchins, D. W. Lamson, R. Rua, C. Milewski and B. Maryanaff, J. Org. Chem., 1971, 36, 803; (c) Y. Qian, G. Li, X. Zheng and Y. Z. Huang, Synlett, 1991, 489; (d) G. Feghouli, R. Vanderesse, Y. Fort and P. Caubere, J. Chem. Soc., Perkin Trans. 1, 1989, 2069; (e) H. Suzuki, H. Manabe, T. Kawaguchi and M. Inouye, Bull. Chem. Soc. Jpn., 1987, 60, 771; (f) M. Husain, S. S. Bhattacharjee, R. A. Lal and H. Askari, Ind. J. Chem., 1989, 28B, 1077.
4. (a) Houben-Weyl, Methoden der Organischen Chemie, Bd. X/2, Georg Thieme Verlag, Stuttgart, 1967, p. 699; (b) G. A. Olah, J. Am. Chem. Soc., 1959, 81, 3165; (c) A. Furst and R. E. Moore, J. Am. Chem. Soc., 1957, 79, 5492; (d) J. S. Clovis and G. S. Hammond, J. Org. Chem., 1963, 28, 3291.
5. C. Yuan, G. Wang, H. Feng, J. Chen and L. Maier, Phosphorus, Sulfur Silicon Relat. Elem., 1993, 81, 149.
6. R. W. Fitch and F. A. Luzzio, Tetrahedron Lett., 1994, 6013.
7. D. Prajapati, H. N. Borah, J. S. Sandhu and A. C. Ghosh, Synth. Commun., 1995, 4025.
8. D. E. Sargent and G. W. Pedlow, Jr., U.S. Patent, 1948, P2570866 (Chem. Abstr., 1952, 46, 4568b).
9. (a) J. M. Khurana and A. Sehgal, J. Chem. Soc., Chem. Commun., 1994, 571; (b) J. M. Khurana, A. Sehgal, A. Gogia, A. Manian and G. C. Maikap, J. Chem. Soc., Perkin Trans. 1, 1996, 2213.
10. J. B. Conant and R. E. Schultz, Org. Synth., 1980, Coll. Vol. II, 224.
11. Vogel's Textbook of Practical Organic Chemistry, ELBS/Longman, 1987, p. 724.
12. Prepared from p-nitrophenol, analogous to the preparation of anisole from phenol, ref. 11, p. 755.
13. Dictionary of Organic Compounds, 5th edn., ed. J. Buckingham, Chapman and Hall, New York, 1982.