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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 5
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Original Articles

Ferric Chloride–Promoted Efficient and Facile BOC Protection of Amines

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Pages 715-719 | Received 25 Oct 2009, Published online: 31 Jan 2011

REFERENCES

  • (a) Greene , T. W. ; Wutts , P. G. M. Protective Group in Organic Synthesis, , 3rd ed .; John Wiley and Sons : New York , 1999 ; (b) Kocienski , P. J. Protecting Group ; George Thieme Verlag : Stuttgart , 2000 .
  • Stahl , G. L. ; Walter , R. ; Smith , C. W. General procedure for the synthesis of mono-N-acylated 1,6-diaminohexanes . J. Org. Chem. 1978 , 43 , 2285 .
  • Snieckus , V. Directed ortho metalation: Tertiary amide and O-carbamate directors in synthetic strategies for polysubstituted aromatics . Chem. Rev. 1990 , 90 , 879 .
  • Lamothe , M. ; Perez , M. ; Colovray-Gotteland , V. ; Halazy , S. A simple one-pot preparation of N,N′-unsymmetrical ureas from N-Boc-protected primary anilines and amines . Synlett 1996 , 6 , 507 .
  • Thorton , T. J. ; Jarman , M. Metallation of N-(pivaloyl)- and N-(tert-butoxycarbonyl)diflouroanilines: Regiocontrol by flourine in the synthesis of 4-methoxycarbonyl derivatives . Synthesis 1990 , 295 .
  • Boger , D. L. ; Mckie , J. A. An efficient synthesis of 1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-one CBI: An enhanced and simplified anaolg of the CC-1065 and duocarmycin alkylation subunits. J. Org. Chem. 1995, 60, 1271.
  • Muchowski , J. M. ; Venuti , M. C. Ortho fictionalization of N-(tert-butoxycarbonyl)aniline . J. Org. Chem. 1980 , 45 , 4798 .
  • (a) Barlin , G. B. ; Pfleiderer , W. Ionization constants of heterocyclic substances, part IX: Protonation of aminopyridones and aminopyrimidones . J. Chem. Soc. B 1971 , 1425 ; (b) Darnbrough , S. ; Mervic , M. ; Condon , S. M. ; Burns , C. J. An improved synthesis of N-BOC-protected aryl amines . Synth. Commun. 2001 , 31 , 3273 .
  • Maeda , H. ; Suzuki , M. ; Sugano , H. ; Mayamura , M. ; Ishida , R. Synthesis and central nervous system actions of thyrotropin-releasing hormone analogs containing a 1-oxo-1,2,3,4-tetrahydroisoquinoline moiety . Chem Pharm. Bull. 1988 , 36 , 190 .
  • Arya , D. P. ; Warner , P. M. ; Jebaratnam , D. J. Development of new DNA binding and cleaving molecules: Design, synthesis, and activity of a bisdiazonium salt . Tetrahedron Lett. 1993 , 34 , 7823 .
  • Kelly , T. A. ; McNeil , D. W. A simple method for the protection of aryl amines as their t-butylcarbomyl (BOC) derivatives . Tetrahedron Lett. 1994 , 35 , 9003 .
  • Pandey , R. K. ; Dagade , S. P. ; Upadhyay , R. K. ; Dongare , M. K. ; Kumar , P. A facile procedure for tert-butoxycarbonylation of amines promoted by yttriazirconia-based strong Lewis acid catalyst . Arkivoc 2002 , 28 .
  • Heydari , A. ; Hosseini , S. E. Lithium perchlorate–catalysed BOC protection of amines and amine drivatives . Adv. Synth. Catal. 2005 , 347 , 1929 .
  • Bartoli , G. ; Bosco , M. ; Locatelli , M. ; Marcantoni , E. ; Massaccesi , M. ; Melchiorre , P. ; Sambri , L. A Lewis acid–mediated protocol for the protection of aryl amines as their BOC derivatives . Synlett 2004 , 10 , 1794 .
  • Sharma , G. V. M. ; Reddy , J. J. ; Lakshmi , P. S. ; Krishna , P. R. Rapid and facile Lewis acid–catalysed BOC protection of amines . Tetrahedron Lett. 2004 , 45 , 6963 .
  • Upadhyaya , D. J. ; Barge , A. ; Stefania , R. ; Crovotto , G. Efficient, solventless N-BOC protection of amines carried out at room temperature using sulfamic acid as recyclable catalyst . Tetrahedron Lett. 2007 , 48 , 8318 – 8322 .
  • Chankeshwara , S. V. ; Chakraborti , A. K. Indium(II) halides as new and highly efficient catalyst for N-tert-butoxycarbonylation of amines . Synthesis 2006 , 16 , 2784 – 2788 .
  • Kametani , T. ; Noguchi , I. ; Nyu , K. ; Takano , S. A novel formation of the indole derivatives by phenolic oxidative coupling . Tetrahedron Lett . 1970 , 723 .
  • Cherest , M. ; Lusinchi , X. A novel electrophilic N-amidation via electron deficient complexes: Action of ferric chloride on N-acetyloxyamides . Tetrahedron Lett. 1989 , 30 , 715 .
  • Schirch , P. F. T. ; Boekelheide , V. [2.2.2.2.2](1,2,3,4,5)Cyclophane . JACS 1979 , 101 , 3125 .
  • Broka , C. A. Total synthesis of phleigchrome, calphostin A, and calphostin D: Unusual stereoselective and stereospecific reactions in the synthesis of perylenequinones . Tetrahedron Lett. 1991 , 32 , 859 .
  • Poupart , M. A. ; Paquette , L. A. Conformational consequences of intramolecular cyclopropanation within small bicyclic systems: Synthesis and desymmetrization of 1-methyltricyclo[2.2.2.0]octane-3,5-dione . Tetrahedron Lett . 1988 , 29 , 269 .

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