Pyridopyrimidines. 7. Ribonucleosides structurally related to the antitumor antibiotic sangivamycin

Anderson, Gary L.; Broom, Arthur D.

doi:10.1021/jo00426a014

Cited by 28 publications

(10 citation statements)

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“…Iminophosphorane 3 reacted with phenyl isocyanate to give carbodiimide 4, which was further treated with phenols or ethenol to produce 2-substituted 5,8,9-trimethyl-3-phenyl-thieno [3',2'-5,6]pyrido [4,3-d]pyrimidin-4(3H)-ones 5 in presence of catalytic amount of K 2 CO 3 or EtONa. The structures of compounds 5 were confirmed by 1 Introduction.…”

mentioning

confidence: 73%

“…The mixture was treated with triethylamine (8.0 mL), then stirred for 18~24 h at 0 °C, the solution was condensed and the residue was recrystallized from CH 3 CH 2 OH to give iminophosphorane 3 in yield 93%, Colorless crystals, mp 174~175 °C. 1 To a solution of iminophosphorane 3 (0.525 g, 1 mmol) in anhyd CH 2 Cl 2 (10 mL) was added aromatic isocyanate (1.1 mmol) under N 2 at r.t. After the reaction mixture was left unstirred for 5-12 h, the solvent was removed under reduced pressure and Et 2 O/petroleum ether was added to precipitate triphenylphosphine oxide. Removal of the solvent gave carbodiimides 4, which were used directly without further purification.…”

Section: Preparation Of Iminophosphoranementioning

confidence: 99%

“…The derivatives of heterocycles containing pyridopyrimidine system are of great importances because of their remarkable biological properties [1]. For example, some pyridopyrimidine derivatives were used as a novel class of adenosine kinase inhibitors [2,3].…”

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confidence: 99%

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A facile synthesis of 2‐substituted thieno[3′,2′‐5,6]‐pyrido[4,3‐d]pyrimidin‐4(3H)‐ones

Liu

Ren

et al. 2006

Journal of Heterocyclic Chem

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The thienopyridine derivative 2, obtained from reaction of acetoacetic ester with 1 in the presence of tin tetrachloride, was treated with triphenylphosphine in hexachloroethane and Et3N to give iminophosphorane 3. Iminophosphorane 3 reacted with phenyl isocyanate to give carbodiimide 4, which was further treated with phenols or ethenol to produce 2‐substituted 5,8,9‐trimethyl‐3‐phenyl‐thieno[3′,2′‐5,6]pyrido[4,3‐d]pyrimidin‐4(3H)‐ones 5 in presence of catalytic amount of K2CO3 or EtONa. The structures of compounds 5 were confirmed by 1H NMR, IR, MS, and elemental analysis.

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confidence: 73%

Section: Preparation Of Iminophosphoranementioning

confidence: 99%

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A facile synthesis of 2‐substituted thieno[3′,2′‐5,6]‐pyrido[4,3‐d]pyrimidin‐4(3H)‐ones

Liu

Ren

et al. 2006

Journal of Heterocyclic Chem

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“…structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL. Many pyridopyrimidines exhibit pharmaceutical and germicidal activities (Anderson & Broom, 1977 (Ismail & Wibberley, 1967).…”

Section: S1-c7mentioning

confidence: 99%

3-(4-Chlorophenyl)-5-methyl-2-propylamino-8,9,10,11-tetrahydro-2-benzothieno[2′,3′;2,3]pyrido[4,5-d]pyrimidin-4(3H)-one

Liu

Chen

et al. 2005

Acta Cryst E

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The asymmetric unit of the title compound, C23H23ClN4OS, contains two crystallographically independent molecules in which the orientations of the propylamine group and chlorophenyl rings with respect to the fused ring system are different. The terminal cyclohexene ring adopts a half‐chair conformation. The crystal packing is stabilized by N—H⋯O, N—H⋯N and C—H⋯O hydrogen bonds and π–π interactions.

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“…Pyrido [2,3-d]pyrimidines, the 5-deaza analogues of pteridines are known to possess a variety of biological properties [1][2][3][4][5][6][7][8]. Recently, these compounds have been reported as dihydrofolate reductase inhibitors and antitumor agents [9,10].…”

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confidence: 99%

Pyridopyrimidines. X. Synthesis of 3‐Substituted 2‐Thioxo‐5,7‐dimethylpyrido[2,3‐d] pyrimidin‐4(3H)‐ones and their S‐Alkylation Under Phase Transfer Conditions

Dave¹,

Patel²

2001

Journal of Heterocyclic Chem

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2- pyrimidin-4(3H)-ones 3 were synthesized by the cyclocondensation of 2-amino-3-carbethoxy-4,6-dimethylpyridine 1 with methyl-N-aryldithiocarbamates 2 and compared with the condensation between 1 and aryl isothiocyanates 4. When a comparative study of N vs S alkylation of ambident 2-thioxo-5,7-dimethylpyrido[2,3-d]pyrimidin-4(3H)-ones 3 was carried out under liquid-liquid and solid-liquid phase transfer conditions using various alkylating agents 5, the S-alkylated products 6 were obtained exclusively and selectively. Therefore, in continuation of our interest in fused pyrimidines and phase transfer catalysed alkylation of ambident heterocyclic system [22], it was of interest to synthesize 2-thioxo-5,7-dimethylpyrido[2,3-d]pyrimidin-4(3H)-ones, which is an ambident system, for the comparative study of N vs. S alkylation under liquid-liquid (L-L) and solid-liquid (S-L) phase transfer conditions. Further, the required 2-thioxo-5,7-dimethylpyrido[2,3-d]pyrimidin-4(3H)-ones as were synthesized for the first time using methyl-N-aryldithiocarbamates and compared with the previously reported method using aryl isothiocyanates.When 2-amino-3-carbethoxy-4,6-dimethylpyridine (1) was cyclocondensed with methyl-N-aryldithiocarbamates (2), 3-substituted 2-thioxo-5,7-dimethylpyrido[2,3-d]-pyrimidin-4(3H)-ones 3 were obtained in 55-69% yields. The reaction is supposed to proceed via in situ cyclization of the intermediate N 1 -substituted-N 2 -[2-(3-carbethoxy-5,6-dimethylpyridyl)]thioureas (Method A). The same compounds 3 were prepared by the cyclocondensation reaction of 1 and aryl isothiocyanates 4 (Method B) according to the method reported by Dave et al. [13,14] and the result was found to be identical (Scheme 1).

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Pyridopyrimidines. 7. Ribonucleosides structurally related to the antitumor antibiotic sangivamycin

Cited by 28 publications

References 5 publications

A facile synthesis of 2‐substituted thieno[3′,2′‐5,6]‐pyrido[4,3‐d]pyrimidin‐4(3H)‐ones

A facile synthesis of 2‐substituted thieno[3′,2′‐5,6]‐pyrido[4,3‐d]pyrimidin‐4(3H)‐ones

3-(4-Chlorophenyl)-5-methyl-2-propylamino-8,9,10,11-tetrahydro-2-benzothieno[2′,3′;2,3]pyrido[4,5-d]pyrimidin-4(3H)-one

Pyridopyrimidines. X. Synthesis of 3‐Substituted 2‐Thioxo‐5,7‐dimethylpyrido[2,3‐d] pyrimidin‐4(3H)‐ones and their S‐Alkylation Under Phase Transfer Conditions

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