The synthesis of pyrimido[4,5-c] pyridazines and pyrido[2,3-d]pyrimidines related to toxoflavin and fervenulin

4-Deazatoxoflavin (1,6-dimethyl-1,5,6,7-tetrahydropyrimido[4,5-c]-5,7-pyridazinedione) (7) and several other 4-deazatoxoflavin and 4-deazafervenulin analogs have been prepared with the required intermediates. 3,5,7-Trimethyl-1,2,3,4-tetrahydropyrido[2,3-d]-2,4-pyrimidinedione (19) and 8-phenyl-3,5,7-trimethyl-2,3,4,8-tetrahydropyrido[2,3-d]-2,4-pyrimidinedione (20) were also prepared.

[1]  T. Kinoshita,et al.  Studies on the Pyridazine Derivatives. XIV. Synthesis and Reaction of Pyrimido [4, 5-c] pyridazines , 1971 .

[2]  C. Cheng,et al.  Synthesis of 5,7-dioxo-3-methyl-5,6,7,8-tetrahydropyrimido[5,4-e]-as-triazine. , 1968, Journal of medicinal chemistry.

[3]  R. Castle,et al.  The synthesis of pyrimido[4,5‐c]pyridazines and pyrimido[5,4‐c]pyridazines , 1968 .

[4]  C. Price,et al.  Pyrido[2,3-d]pyrimidines from Malonaldehydes1 , 1962 .

[5]  W. Pfleiderer,et al.  Pteridine, XXI1) Über die Synthese und Struktur von N‐8‐substituierten 2.4.7‐Trioxo‐hexahydropteridin‐carbonsäuren‐(6) , 1962 .

[6]  R. K. Robins,et al.  Antibiotics. I. Synthesis of 1,6-Dimethyl-5,7-dioxo-1,5,6,7-tetrahydropyrimido [5,4-e]as-Triazine (Toxoflavin) and Related Compounds , 1962 .

[7]  R. K. Robins,et al.  Communications- The Structure of Fervenulin, A New Antibiotic , 1961 .

[8]  W. Berends,et al.  On the origin of the toxicity of toxoflavin. , 1961, Biochimica et biophysica acta.

[9]  Reuben G. Jones Reaction of Some Heterocyclic vic-Dicarboxamides with Alkaline Hypobromite , 1960 .

[10]  W. Pfleiderer,et al.  Untersuchungen in der Pyrimidinreihe VIII. Über neue Synthesen von Pyrazolo[3.4‐d]‐ und 1.2.4‐Triazino[6.5‐d]‐pyrimidinen , 1958 .

[11]  H. Ferch,et al.  Untersuchungen in der Pyrimidinreihe IX. Über die Synthese von Pyridazino[3.4‐d]‐pyrimidinen , 1958 .

[12]  R. K. Robins,et al.  Studies on Condensed Pyrimidine Systems. XIX. A New Synthesis of Pyrido [2,3-d] pyrimidines. The Condensation of 1,3-Diketones and 3-Ketoaldehydes with 4-Aminopyrimidines , 1958 .

[13]  A. Dornow,et al.  Über weitere Umsetzungen von 2‐Amino‐ und 2‐Oxynicotinsäurederivaten Synthesen stickstoffhaltiger Heterocyclen, XIV. Mitteilung , 1957 .

[14]  R. K. Robins,et al.  Studies on Condensed Pyrimidine Systems. XIV. Some Pyrido [3,2-d]pyrimidines , 1956 .

[15]  H. Rydon,et al.  853. Polyazanaphthalenes. Part IV. Further derivatives of 1 : 3 : 5- and 1 : 3 : 8-triazanaphthalene , 1956 .

[16]  H. Rydon,et al.  216. Polyazanaphthalenes. Part III. Some derivatives of 1 : 3 : 5- and 1 : 3 : 8-triazanaphthalene , 1956 .

[17]  R. K. Robins,et al.  Studies on Condensed Pyrimidine Systems. XII. Synthesis of Some 4- and 2,4-Substituted Pyrido[2,3-d]pyrimidines , 1955 .

[18]  A. Tytell,et al.  Xanthothricin, a new antibiotic. , 1954, Antibiotics & chemotherapy.