Synthesis of 1-Substituted 5-Aminoimidazole-4-carbaldehydes and 8-Amino-1-(2-fluorobenzyl)imidazo[4’,5’:5,6]pyrido[2,3-d]pyrimidine

Brian L. Booth; Robert A. Carpenter; Gaby Morlock; Zahid Mahmood; Robin B. Pritchard

doi:10.1055/s-2001-18705

PAPER

Synthesis of 1-Substituted 5-Aminoimidazole-4-carbaldehydes and 8-Amino-1-(2-fluorobenzyl)imidazo[4’,5’:5,6]pyrido[2,3-d]pyrimidine

Brian L. Booth*, Robert A. Carpenter, Gaby Morlock, Zahid Mahmood, Robin B Pritchard
Department of Chemistry, UMIST, P.O. Box 88, Manchester M60 1QD, U.K.
Fax: +44(161)2004484; e-Mail: brian.booth@umist.ac.uk;

Abstract

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Abstract

The syntheses of a number of 1-substituted 5-aminoimidazole-4-carbaldehydes 3, by the reduction of the corresponding 5-amino-4-cyanoimidazole derivatives is reported using LiAlH(OEt)₃, prepared in situ from LiAlH₄ and ethyl acetate. The compounds of type 1 are useful intermediates for the synthesis of elongated adenine derivatives.

Key words

heterocycles - imidazoles - cyanides - aldehydes - imidazo[4’,5’:5,6]pyrido[2,3-d]pyrimidines

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Referenzen

References

1a Stephen H. J. Chem. Soc. 1925, 1874

1b Stephen H. J. Chem. Soc. 1930, 2786

2a Reiman E. Liebigs Ann. Chem. 1978, 1963

2b Weistock LT. O’Brien DE. Cheng CC. J. Med. Chem. 1968, 11: 1238

2c Taurins A. Khnouw VT. Can. J. Chem. 1973, 51: 1741

3a Bredereck H. Simchen G. Traut H. Chem. Ber. 1967, 100: 366

3b Tieckelmann H. Guthrie R. Nairn JG. J. Org. Chem. 1960, 25: 1257

3c Arpad G. Odon F. Oszkár F. Magy. Kem. Foly. 1955, 61: 112

4 Perandones F. Soto JL. J. Heterocycl. Chem. 1997, 34: 107

5 Alves MJ. Booth BL. Al-Duaij OKh. Eastwood P. Nezhat L. Proença MFJRP. Ramos AS. J. Chem. Res. (M) 1993, 2701

6 Butula I. Liebigs Ann. Chem. 1969, 729: 73

7 Brown HC. Garg CP. J. Am. Chem. Soc. 1964, 86: 1085

8a Kelley JL. Krochmal MP. Linn JA. McLean EW. Soroko FE. J. Med. Chem. 1988, 31: 606

8b Kelley JL. Krochmal MP. Linn JA. McLean EW. Soroko FE. J. Med. Chem. 1988, 31: 1005

9 Al-Shaar AHM. Chambers RK. Gilmour DW. Lythgoe DJ. McClenaghan I. Ramsden CA. J. Chem. Soc., Perkin Trans. 1 1992, 2789

10 Harris PA. Pendergast W. J. Heterocycl. Chem. 1996, 33: 319

11 Booth BL. Costa FAT. Mahmood Z. Pritchard RG. Proença MFJRP. J. Chem. Soc., Perkin Trans. 1 1999, 1853

12 Gilmore CJ. J. Appl. Crystallogr. 1984, 17: 42

13

Beurskens, P. T. DIRDIF: Direct Methods for Difference Structures - An Automatic Procedure for Phase Extension and Refinement of Difference Structure Factors, Technical report 1984/1, Crystallography Laboratory: Toernooiveld, 6525 Ed, Nijmegen, 1984.