Preparation of substituted semicarbazides from corresponding amines and hydrazines via phenyl carbamates

Tetrahedron Letters

Volumn 55, Issue 9, 2014, Pages 1540-1543

  Hron, Rebecca ^a,b   Jursic, Branko S ^a,b  

^a UNIVERSITY OF NEW ORLEANS   (United States)

^b Stepharm   (United States)

Author keywords

Alkylsemicarbazides; Arylsemicarbazides; Carbamates; Hydrazine; Semicarbazides

Indexed keywords

EID: 84894096993     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2014.01.052     Document Type: Article

References (39)

1. S.R. Sandler, and W. Karo Organic Functional Group Preparations Chapter 8: Semicarbazide. 2nd ed. Vol II 1986 Academic Press 213 232
2. Bailey, B. R. '4-Alkyl and aryl semicarbazides as oxygen scavengers' US Patent 5, 904, 857 (1999).
3. Okawara, T.; Imai, K.; Ochiai, T. 'Free radical scavenger containing semicarbazide derivative' International Patent Pub. No. WO/2006/093124.
4. Brandl, M.; Ebner, M.; Krimmer, H.P. 'Alkyl or dialkyl semicarbazones as hardeners for epoxy resins' International Patent WO2013072354.
5. For instances see: S. Lesniak, A.M. Pieczonka, S. Jarzynski, K. Justyna, and M. Rachwalski Tetrahedron: Asymmetry 24 2013 1341 1344
6. For instance see: Manning, T. J.; Ogburn, R. N.; Ledwitch, K. V.; Phillips, D. R.; Wylie, G. P. 'Copper ion delivery platform for pharmaceutical agents' US Patent US20130237511 A1.
7. H. Beraldo, and D. Gambinob The wide pharmacological versatility of semicarbazones, thiosemicarbazones and their metal complexes Mini Rev. Med. Chem. 4 2004 31 39
8. N. Latyshko, O. Gudkova, and M. Dmytrenko Semicarbazide as potent source of formaldehyde and nitric oxide formation Drugs Therapy Studies 2 2012 43 47
9. S.G. Swarts, M. Zhang, L. Yin, C. Liu, Y. Tan, Y. Cao, M. Swarts, D.J. Olek, L. Schwartz, L. Zhang, S. Yang, S.B. Zhang, K. Zhang, S. Ju, S. Vidyasagar, L. Zhang, and P. Okunieff Antioxidant properties of select radiation mitigators based on semicarbazone and pyrazole derivatives of curcumin Adv. Exp. Med. Biol. 701 2011 291 297
10. I. Perkovic, S. Trsinar, J. Zanetic, M. Kralj, I. Martin-Kleiner, J. Balzarini, D. Hadjipavlou-Litina, A.M. Katsori, and B. Zorc Novel 1-acyl-4-substituted semicarbazide derivatives of primaquine-Synthesis, cytostatic, antiviral and antioxidative studies J. Enzyme Inhib. Med. Chem. 28 2013 601 610
11. Buchstaller, H.P.; Finsinger, D.; Stieber, F.; Wiesner, M.; Amendt, C.; Sirrenberg, C.; Zenke, F.; Grell, M. 'Semicarbazide derivatives as kinase inhibitors' US Patent Pub. No. US 2009/0253688 A1.
12. Dai, D.; Bolken, T.; Amberg, S. M.; Hruby, D. E.; Bailey, T. R. 'Sulfonyl semicarbazides, semicarbazides and ureas, pharmaceutical compositions thereof, and methods for treating hemorrhagic fever viruses, including infections associated with arenaviruses' US patent 8, 410, 149 B2 (2013).
13. D. Nardi, E. Massarani, A. Tajana, L. Degen, and M.J. Magistretti Antibacterial nitrofuran derivatives. I. 5-Nitro-2-furaldehyde semicarnazones and thiosemicarbazones J. Med. Chem. 10 1967 530 533
14. V. Laxmi, and B. Rajitha Synthesis and antimicrobial activity od newer indole semicarbazones Med. Chem. Res. 21 2012 85 90
15. S.N. Pandeya, T. Srivastava, M. Gangwar, B. Bihari, and G. Nath Synthesis and antimicrobial activity of 1-naphthylamine based acetophenone semicarbazones Med. Chem. Drug Disc. 3 2012 94 102
16. M. Sighal, and A. Paul Evaluation of antibacterial activity of synthesized methylsemicabazone derivatives Int. J. Pharm. Sci. Res. 2 2011 372 375
17. M.A. Soiza, S. Johann, L.A.R. dos Santos Lima, F.F. Campos, I.C. Mendes, H. Beraldo, E.M. Souza-Fagundes, P.S. Cisalpino, C.A. Rosa, T.M. Alves, N.P. de Sa, and C.L. Zani The antimicrobial activity of lapachol and its thiocarbazone and semicarbazone derivatives Mem. Inst. Oswaldo Cruz. 108 2013 342 351
18. M. Giannella, and F. Gualtieri Research on substances with antiviral action: carbamates, thiosemicarbazones and semicarbazones of cyclic alpha-oxyiminoketones Farmaco Sci. 25 1970 509 518
19. V. Mishra, S.N. Pandeya, E. DeClercq, C. Pannecouque, and M. Witvrouw Synthesis of aryl semicarbazones of 4-aminoacetophenone and their anti-HIV activity Pharm. Acta Helv. 73 1998 215 218
20. Shubert, U. 'Semicarbazone protease inhibitors for treating HIV and hepatitis infection' International Patent WO2011089166 A1.
21. S.N. Pandeya Semicarbazone-a versatile therapeutic pharmacophore for fragment based anticonvulsant drug design Acta Pharm. 62 2012 263 286
22. A.S. Wheeler '4-phenylsemicarbazide' Org Synth. Coll. I 1941 450 451
23. S.K. Kashaw, V. Kashaw, P. Mishra, and N.K. Jain Design, synthesis and potential CNS activity of some novel 1-(4-substituted-phenyl)-3-(4-oxopropyl-4H- quinazolin-3yl)-urea ARKIVOC 14 2008 17 26
24. S. Smitha, S.N. Pandeya, J.P. Stables, and S. Ganapathy Anticonvulsant and sedative-hypnotic activity of N-acetyl/methyl isatin derivatives Sci. Pharm. 76 2008 621 636
25. A. Singh, C. Pande, P. Gahtori, S.N. Pandeya, and J.P. Stables Design and synthesis of some novel 4-(4-substituted aryl) semicarbazones as anticonvulsant agents Indian J. Pharm. Sci. 72 2010 363 367
26. 6-Cyclopentyl-2-(3-phenylaminocarbonyltriazene-1-yl) adenosine (TCPA), a very selective agonist with high affinity for the human adenosine A1 receptor J. Med. Chem. 46 2003 1492 1503
27. I.J. Kang, L.W. Wang, T.A. Hsu, A. Yueh, C.C. Lee, Y.C. Lee, C.Y. Lee, Y.S. Chao, S.R. Shih, and J.H. Chern Isatin-beta-thiosemicarbazones as potent herpes simplex virus inhibitors Biorg. Med. Chem. Lett. 21 2011 1948 1952
28. M.N. Aboul-Enein, A.A. El-Azzouny, M.I. Attia, Y.A. Maklad, K.M. Amin, M. Abdel-Rehim, and M.F. El-Behairy Design and synthesis of novel stiripentol analogues as potent anticonvulsants Eur. J. Med Chem. 57 2012 360 369
29. S. Mallakpour, and Z. Rafiee One-pot synthesis of 4-substituted 1,2,4-triazolidine-3,5-diones Synlett 2007 1255 1256
30. Y. Liu, W.Q. Lu, K.Q. Cui, W. Luo, J. Wang, and C. Guo Synthesis and biological activity of novel artemisinin derivatives as cysteine protease falcipain-2 inhibitors Arch. Pharmacol. Res. 35 2012 1525 1531
31. C. Sheng, X. Che, W. Wang, S. Wang, Y. Cao, Z. Miao, J. Yao, and W. Zhang Design and synthesis of novel triazole antifungal derivatives by structure-based bioisosterism Eur. J. Med. Chem. 46 2011 5276 5282
32. For instance see: E.W. Schmidt Hydrazine and its derivatives: preparation, properties and applications 2nd ed. 2001 Wiley
33. S. Ilieva, D. Nalbantova, B. Hadjieva, and B. Galabov Aminolysis of phenyl N-phenylcarbamate via an isocyanate intermediate: Theory and experiment" J. Org. Chem. 78 2013 6440 6449
34. Weber, H. W. 'Process for preparation alkyl isocyanates' US Patent 4, 123, 450 (1978).
35. For instance see: Q. Liu, N.W. Luedtke, and Y. Tor A simple conversion of amines into monosubstituted ureas in organic and aqueous solvents Tetrahedron Lett. 42 2001 1445 1447
36. O. Kreye, H. Mutlu, and M.A.R. Meier Sustainable routes to polyurethane precursors Green Chem. 15 2013 1431 1455
37. L. Zhang, W. Xia, B. Wang, Y. Luo, and W. Lu Convenient synthesis of sorafenib and its derivatives Synth. Commun. 41 2011 3140 3146
38. X. Guo, J. Shang, J. Li, L. Wang, Y. Ma, F. Shi, and Y. Deng Green and practical synthesis of carbamates from ureas and organic carbonates Synth. Commun. 41 2011 1102 1111
39. P. Terech, and R.G. Weiss Low molecular mass gelators of organic liquids and the properties of their gels Chem. Rev. 97 1997 3133 3159