One-step reductive amidation of nitro arenes: Application in the synthesis of Acetaminophen™

Tetrahedron Letters

Volumn 47, Issue 11, 2006, Pages 1861-1864

  Bhattacharya, Apurba ^a   Purohit, Vikram C ^a   Suarez, Victor ^a   Tichkule, Ritesh ^a   Parmer, Gaurang ^a   Rinaldi, Frank ^b  

^a TEXAS A AND M UNIVERSITY KINGSVILLE   (United States)

^b BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PARACETAMOL; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SURFACTANT;

AMIDATION; ARTICLE; CATALYSIS; DRUG SYNTHESIS;

EID: 32244436062     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.09.196     Document Type: Article

References (27)

1. Z. Zhang, A. Yin, J.F. Kadow, N.A. Meanwell, and T.J. Wang J. Org. Chem. 69 2004 1360
2. Lidocaine S. Budavari 12th ed. Merck Index Vol. 5505 1996 Merck 936
3. R. Ballini, G. Bosica, and D. Fiorini Tetrahedron 59 1998 1143
4. A.R. Katritzky, H.-Y. He, and K. Suzuki J. Org. Chem. 65 2000 8210
5. S. Nishimura Bull. Chem. Soc. Jpn. 34 1961 32
6. R. Adams, and F.L. Cohen Org. Synth. Coll. 1 1932 240
7. G.D. Mendennhall, and P.A.S. Smith Org. Synth. Coll. 5 1973 829
8. H. Adkins, and R. Connar J. Am. Chem. Soc. 53 1931 1091
9. R.R. Davies, and H.H. Hodgson J. Chem. Soc. 1943 281
10. H.S. Broadbent, L.H. Slaugh, and N.L. Jarvis J. Am. Chem. Soc. 76 1954 1519
11. T. Tsukinoki, and H. Tsuzuki Green. Chem. 3 2001 37 38
12. H.H. Hodgson, and J.S. Whitehurst J. Am. Chem. Soc. 1945 202
13. L. Wang, L. Zhou, and Zhang Synlett 1999 1065
14. M.R. Pitts, J.R. Harrison, and C.J. Moody J. Chem. Soc., Perkin Trans. 1 2001 955
15. J.A. Blackie, N.J. Turner, and A.S. Wells Tetrahedron Lett. 38 1997 3043
16. B.H. Kim, R. Han, F. Piao, Y.M. Jun, W. Baik, and B.M. Lee Tetrahedron Lett. 44 2003 77 and referenced cited therein
17. J.R. Hwuk, F.F. Wong, and M.-J. Shiao J. Org. Chem. 57 1992 5254
18. J.-J. Shiao, L. Long-Li, K. Wei-Shan, P.-Y. Lin, and J.R. Hwu J. Org. Chem. 58 1993 4742
19. (c) The formation of nitrosobenzene via an alternate pathway involving the nucleophilic attack of RS(-) on the oxygen of the nitro functionality can not be ruled out.
20. (a) Average bond energy of C-S is 65 kcal/mol, C-C is 83 kcal/mol and C-Si is 83 kcal/mol; data obtained from Michigan State University-Organic home page website (http://www.cem.msu.edu/~reusch/OrgPage/bndenrgy.htm).
21. For analogous O- to C-acyl migration, see Baker-Venkataraman rearrangement: K. Bowden, and M. Chehel-Amiran J. Chem. Soc., Perkin Trans. 2 1986 2039
22. -). The S-S bond formation has precedence in peptide chemistry of cysteine. The resulting dithiane can act as an effective acylating agent.
23. A. Bhattacharya, V.C. Purohit, and F. Rinaldi Org. Proc. Res. Dev. 7 2003 254
24. J. Rebeck Angew. Chem., Int. Ed. Engl. 29 1990 245
25. J. March Adv. Org. Chem. 4th ed. 1992 John Wiley 82 93 and references cited therein
26. 1H NMR spectra were consistent with the products in coupling and chemical shift data.
27. (b) For all the compounds GC-MS analysis (Shimadzu QP5050A) in the EI mode provided similarity index match of >90% compared to the authentic samples in the NIST-98 database.