Syntheses of 4-[(1H,3H)-pyrimidine-2,4-dion-1-yl]- and 4-[(1H,3H)-5- methylpyrimidine-2,4-dion-1-yl]-1,6-heptadienes

Synthetic Communications

Volumn 35, Issue 7, 2005, Pages 1003-1010

  Bouhadir, Kamal H ^a   Zhou, Jing Lan ^b   Shevlin, Philip B ^b  

^a AMERICAN UNIVERSITY OF BEIRUT   (Lebanon)

^b AUBURN UNIVERSITY   (United States)

Author keywords

Carbocyclic nucelosides; Heptadiene; Isocyanate; Thymine; Uracil

Indexed keywords

4 (5 METHYLPYRIMIDINE 2,4 DION 1 YL) 1,6 HEPTADIENE; 4 (PYRIMIDINE 2,4 DION 1 YL) 1,6 HEPTADIENE; 4 ISOCYANATO 1,6 HEPTADIENE; ALKADIENE; HEPTANE DERIVATIVE; ISOCYANIC ACID DERIVATIVE; NUCLEIC ACID BASE; OLIGONUCLEOTIDE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROLYSIS; SYNTHESIS;

EID: 16444385851     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-200051721     Document Type: Article

References (8)

1. Tsai, J. Y.; Bouhadir, K. H.; Zhou, J. L.; Webb, T. R.; Sun, Y.; Shevlin, P. B. Synthesis of purine- and pyrimidine-substituted heptadienes: The stereochemistry of cyclization and cyclopolymerization products. J. Org. Chem. 2003, 68, 1235-1241.
2. Naim, A.; Mills, G.; Shevlin, P. B. Cyclization of 1,6-heptadienes by α-hydroxy radicals. Tetrahedron Lett. 1992, 33 (45), 6779-6782.
3. Naim, A.; Shevlin, P. B. A simple preparation of 1-substituted uracils. Synth. Commun. 1990, 20 (22), 3439-3442.
4. Israel, M.; Zol, E. C.; Muhammad, N.; Modest, E. J. Synthesis and antitumor evaluation of the presumed cytotoxic metabolites of spermine and N,N′-bis(3-aminopropyl)nonane-1,9-diamine. J. Med. Chem. 1973, 16 (1), 1-5.
5. Hwu, J. R.; Chen, C. N.; Shiaot, S. Silicon-controlled allylation of 1,3-dioxo compounds by use of myltrimethylsilane and ceric ammonium nitrate. J. Org. Chem. 1995, 60, 856-862.
6. Semmelhack, M. F.; Foos, J. S.; Katz, S. Spiro[4.4]nonatetraene and spiro[4.4]nona-1,3,7-triene: Synthesis and properties: Effects of spiroconjugation. J. Amer. Chem. Soc. 1973, 95 (22), 7325-7336.
7. Croxall, W. J.; Van Hook, J. O. Transetherification reactions: Preparation and rearrangement of p-alloxyacrylates. J. Amer. Chem. Soc. 1950, 72 (22), 803-808.
8. Czarnik, A. W.; Leonard, N. J. Confirmation of the structure of the guanine-methylmalondialdehyde reaction product by unequivocal synthesis. J. Org. Chem. 1981, 46(4), 815-819.