Catalytic Activity of 1,3-Dibromo-5,5-dimethylhydantoin (DBH) in the One-Pot Transformation of N-Arylglycines to N-Arylsydnones in the Presence of NaNO₂/Ac₂O under Neutral Conditions: Subsequent Bromination of these Sydnones to their 4-Bromo Derivatives

Abstract

1,3-Dibromo-5,5-dimethylhydantoin (DBH) has been found to efficiently catalyze the one-pot conversion of various N-arylglycines through N-nitrosation and cyclization to sydnones in combination with NaNO₂ and Ac₂O in high yields (80-94%) under mild and neutral conditions. Also, it was shown that DBH can conveniently­ promote the bromination of these sydnones to their 4-bromo substituted congeners in excellent yields in DMF at room temperature.

Key words

nitrosation - N-arylglycines - sydnones - 1,3-dibromo-5,5-dimethylhydantoin (DBH) - bromination

References

• 1a Ohta M. Kato H. In Nonbenzenoid Aromatics   Vol. 1:  Snyder JP. Academic Press; New York: 1969.  p.146 
• 1b Stewart FHC. Chem. Rev.  1964,  64:  129 
• 2 Earl JC. Mackney AW. J. Chem. Soc.  1935,  899 
• 3a Brooks P. Walker J. J. Chem. Soc.  1959,  4409 
• 3b Ackermann E. Pharmazie  1967,  22:  537 ; Chem. Abstr. 1968, 68, 28171
• 4 Kier LB. Roche EB. J. Pharm. Sci.  1967,  56:  149 
• 5 McCaustland DJ. Burton WH. Cheng CC. J. Heterocycl. Chem.  1971,  8:  89 
• 6a Pala G. Mantegani A. Coppi G. Genova R. Chim. Ther.  1969,  4:  31 ; Chem. Abstr. 1969, 71, 3328
• 6b Kamiya T, Saito Y, and Teraji T. inventors; Fujisawa Pharm. Co., Ltd., Japanese Patent  7232073.  ; Chem. Abstr. 1973, 78, 42592
• 7 Saito Y, and Kamiya T. inventors; Takeda Chem. Ind. Ltd., Japanese Patent  7010510.  ; Chem. Abstr. 1970, 73, 14853
• 8 Turnbull K. J. Heterocycl. Chem.  1985,  22:  965 
• 9 Huisgen R. Grashey R. Gotthardt H. Schmidt R. Angew. Chem.  1962,  74:  29 
• 10 Gelvin CR. Turnbull K. Helv. Chim. Acta  1992,  75:  1931 
• 11 Tin-Lok C. Miller J. Stansfield F. J. Chem. Soc.  1964,  1213 
• 12 Turnbull K. Blackburn TL. Miller J. J. Heterocycl. Chem.  1996,  33:  485 
• 13 Thoman CJ. Voaden DJ. Org. Synth. Coll. Vol. V   Wiley; New York: 1973.  p.962 
• 14 Williams DLH. In The Chemistry of Functional Groups, The Chemistry of Amino, Nitroso, Nitro and Related Groups   Supplement F2:  Patai S. Wiley; Chichester: 1996.  p.665-682  
• 15 Shriner RL. Reynold TL. Fuson C. Curtin DY. Morrill TC. The Systematic Identification of Organic Compounds   6th ed.:  Wiley; New York: 1980.  p.220-223  
• 16 Azarifar D. Zolfigol MA. Maleki B. Synthesis  2004,  1744 
• 17 Azarifar D. Zolfigol MA. Maleki B. Bull. Korean Chem. Soc.  2004,  25:  23 ; Chem. Abstr. 2004, 141, 1029
• 18 Azarifar D. Ghasemnejad-Bosra H. Ramazanian-Lehmali F. Mendeleev Commun.  2005,  209 
• 19 Azarifar D. Ghasemnejad-Bosra H. Zolfigol MA. Tajbaksh M. Heterocycles  2006,  68:  175 
• 20 Eade RA. Earl JC. J. Chem. Soc.  1946,  591 
• 21a Baker W. Ollis WD. Poole VD. J. Chem. Soc.  1949,  307 
• 21b Baker W. Ollis WD. Poole VD. J. Chem. Soc.  1950,  1542 
• 22 Greco CV. Pesce M. Franco JM. J. Heterocycl. Chem.  1966,  3:  391 
• 23 Kier LB. Dhawan D. Fregly MJ. J. Pharm. Sci.  1964,  53:  677 
• 24a Tien HJ. Yeh MY. Huang CY. J. Chin. Chem. Soc.  1985,  32:  461 ; Chem. Abstr. 1987, 106, 102169
• 24b Badami BV. Puranik GS. Indian J. Chem.  1974,  12:  671 ; Chem. Abstr. 1975, 82, 31293
• 25 Lio S. Turnbull K. Synth. Commun.  1996,  26:  1441 
• 26 Puranic GS. Suschitzky H. J. Chem. Soc.  1967,  1006