Sodium borohydride mediated benzylation of 1,3-dimethylbarbituric acid

Heterocyclic Communications

Volumn 5, Issue 6, 1999, Pages 525-528

  Strekowski, Lucjan ^a   Ismail, Mohamed A ^a   Zoorob, Hanafi H ^b  

^a GEORGIA STATE UNIVERSITY   (United States)

^b Mansoura University   (Egypt)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0033270610     PISSN: 07930283     EISSN: None     Source Type: Journal    
DOI: 10.1515/HC.1999.5.6.525     Document Type: Article

References (7)

1. W. Fraser, C. Suckling and H. Wood, J. Chem. Soc., Perkin Trans. 1, 3137 (1990)
2. Z. Budesinsky and M. Protiva, Synthetische Arzneimittel, Akademie-Verlag, Berlin, 1961
3. K. Dudley, I. Davis, D. Kim and F. Ross, J. Org. Chem. 35, 147 (1970)
4. A. Cope, D. Heyl, D. Peck, C. Eide and A. Arroyo, J. Am. Chem. Soc. 63, 356 (1941)
5. 13C NMR (DMSO-d6) δ 162.6, 157.2, 149.9, 141.0, 134.1, 129.6, 128.9, 128.1, 127.0, 88.1, 71.6, 28.8, 28.1, 27.0
6. R. Goehring, T. Greenwood, G. Nwokogu, J. Pisipati, T. Rogers and J. Wolfe, J. Med. Chem. 33, 926 (1990)
7. 4 (1 equiv) and 4-fluorobenzyl chloride (2 equiv) by using the general procedure furnished product (i) in a 77% yield. In a similar way, compound (ii) was obtained in a 67% yield starting with indane-1,3-dione. Although these results demonstrate the generality of our method, much more efficient benzylation reactions of β-diketones are known.