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References (25)
-
W. Pfleiderer, Gotthard Nübel (1961)
Purine, II Zur Struktur des Xanthins und seiner N‐Methyl‐DerivateEuropean Journal of Organic Chemistry, 647
-
S. Esipov, M. Kolosov, L. Saburova (1973)
THE STRUCTURE OF REUMYCINThe Journal of Antibiotics, 26
-
T. Denzel, H. Höhn (1977)
Imidazo [4,5‐c] ‐ and [4,5‐6] pyridinesJournal of Heterocyclic Chemistry, 14
-
E. Taylor, F. Sowinski (1975)
Synthesis of the pyrimido [5,4-e]-as-triazine antibiotics fervenulin and 2-methylfevenulone.The Journal of organic chemistry, 40 16
-
C. Temple, R. Mckee, J. Montgomery (1963)
Pyrimido[5,4-e]-as-triazines. I. The Preparation and Properties of 5-Chloro-1,2-dihydropyrimido[5,4-e]-as-triazine and Some of Its Methyl Derivatives1Journal of Organic Chemistry, 28
-
Bernadette Billings, Judith Wagner, P. Cook, R. Castle (1975)
The synthesis of pyrimido[4,5-c] pyridazines and pyrido[2,3-d]pyrimidines related to toxoflavin and fervenulinJournal of Heterocyclic Chemistry, 12
-
J. Montgomery, C. Temple (1960)
Synthesis of Potential Anticancer Agents. XXIII. 9-Aminohypoxanthine and Related CompoundsJournal of the American Chemical Society, 82
-
N. Leonard, A. Morrice, M. Sprecker (1975)
Linear benzoadenine. A stretched-out analog of adenine.The Journal of organic chemistry, 40 3
-
F. Yoneda, T. Nagamatsu (1973)
Transformation of toxoflavin into fervenulin via 1-demethyltoxoflavinTetrahedron Letters, 14
-
F. Condon, Richard Reece, Daniel Shapiro, D. Thakkar, T. Goldstein (1974)
The influence of hydration on base strength. Part V. Hydrazines and oxyamines. Heats of solution and thermodynamics of ionization of the 20 methyl and ethyl substituted hydrazines. Isomerization equilibria for unsymmetrical hydrazinium ions. Substituent constants (σ* values) for amino-groupsJournal of The Chemical Society-perkin Transactions 1
-
R. Green, L. Stanberry (1977)
Elevation of cyclic AMP in C-1300 murine neuroblastoma by adenosine and related compounds and the antagonism of this response by methylxanthines.Biochemical pharmacology, 26 1
-
H. Yamaguchi, R. Kuwata, F. Yoneda (1978)
Magnetic circular dichroism spectra of some 3-arylfervenulins and 3-aryltoxoflavinsJournal of Heterocyclic Chemistry, 15
-
E. Taylor, J. Barton, W. Paudler (1961)
Studies in Purine Chemistry. X. Some Derivatives of 9-Aminopurines1,2Journal of Organic Chemistry, 26
-
R. Abramovitch, K. Schofield (1955)
Polyazabicyclic compounds. Part I. Preliminary experiments on the bischler and the bamberger synthesis of benzo-1 : 2 : 4-triazinesJournal of The Chemical Society (resumed)
-
S. Schneller, W. Christ (1981)
Correction. Synthesis of lin-Benzofervenulin, lin-Benzotheophylline, and lin-BenzocaffeineJournal of Organic Chemistry, 46
-
M. Croce, G. Kramer, D. Garbers (1979)
Inhibition of alkaline phosphatase by substituted xanthines.Biochemical pharmacology, 28 7
-
F. Yoneda, T. Nagamatsu (1975)
New Syntheses of Fervenulin (1,3-Dimethyl-7-azalumazine) and AnalogsBulletin of the Chemical Society of Japan, 48
-
S. Schneller, W. Christ (1981)
The synthesis of proximal‐benzolumazine, proxirnal‐benzoxanthine, proximal‐benzotheophylline and proximal‐benzocaffeineJournal of Heterocyclic Chemistry, 18
-
J. Williams, S. Lowitt, J. Polson, A. Szentivanyi (1978)
Pharmacological and biochemical activities of some monomethylxanthine and methyluric acid derivatives of theophylline and caffeine.Biochemical pharmacology, 27 11
-
F. Yoneda, T. Nagamatsu (1973)
Transmethylation from toxoflavines to nucleophiles.Journal of the American Chemical Society, 95 17
-
R. Hinman (1958)
Notes - Base Strengths of Some AlkylhydrazinesJournal of Organic Chemistry, 23
-
F. Yoneda, T. Nagamatsu (1975)
A convenient synthesis of toxoflavins, toxoflavin 4-oxides and 1-demethyltoxoflavins.Chemical & pharmaceutical bulletin, 23 9
-
S. Schneller, W. Christ (1981)
The synthesis of “stretched‐out” analogs of lumazine, 6,7‐dimethyllumazine and 2‐amino‐5,6,7,8‐tetrahydro‐6,7‐dimethyl‐4‐pteridinoneJournal of Heterocyclic Chemistry, 18
-
D. Lichtenberg, F. Bergmann, Z. Neiman (1971)
Tautomeric forms and ionisation processes in xanthine and its N-methyl derivativesJournal of The Chemical Society C: Organic
-
E. Glover, Kenneth Rowbottom, D. Bishop (1973)
Synthesis of 3,3′-dimethyl-1,1′-azobenzimidazolium saltsJournal of The Chemical Society-perkin Transactions 1
- Publisher
- Wiley
- Copyright
- Copyright © 1984 Journal of Heterocyclic Chemistry
- ISSN
- 0022-152X
- eISSN
- 1943-5193
- DOI
- 10.1002/jhet.5570210331
- Publisher site
- See Article on Publisher Site
Abstract
Commencing with 7‐chloro‐3‐methylquinazoline‐2,4(1H,3H)‐dione (9a), a five step synthesis of 7‐methylpyrimido(5,4‐g)‐1,2,4‐benzotriazine‐6,8(7H,9H)‐dione (lin‐benzoreumycin, 6) has been accomplished. A synthesis of 1,7‐dimethylpyrimido(5,4‐g)‐1,2,4‐benzotriazine‐6,8(1H,7H)‐dione (lin‐benzotoxoflavin, 5) employing an intermediate from the preparation of 6 (i.e., 7‐chloro‐3‐methyl‐6‐nitroquinazoline‐2,4(1H,3H)‐dione, 9b) was attempted but could not be accomplished beyond the dihydro precursor of 5 (i.e., 12). Compound 9b did lead to successful preparations of 7‐methylimidazo(4,5‐g)quinazoline‐6,8(5H,7H)‐dione (lin‐benzo‐1‐methylxanthine, 7) and 3,7‐dimethylimidazo(4,5‐g)quinazoline‐6,8(5H,7H)‐dione (lin‐benzo‐1,9‐dimethylxanthine, 8) by first reacting 9b with ammonia (for 7) or methylamine (for 8) followed by reductive cyclization in formic acid.
Journal
Journal of Heterocyclic Chemistry – Wiley
Published: May 1, 1984