Chemistry of Heterocyclic Compounds: Fused Pyrimidines Part by Thomas J. Delia

By Thomas J. Delia

Pyridopyrimidines.

Pyrano- and Thiopyranopyrimidines.

Pyrimidopyrimidines.

Pyrimidopyridazines.

Pyrimidooxazines and Pyrimidothiazines.

Pyrimidotriazines.

Index.Content:
Chapter I Pyridopyrimidines (pages 1–117):
Chapter II Pyrano? and Thiopyranopyrimidines (pages 119–147):
Chapter III Pyrimidopyrimidines (pages 149–191):
Chapter IV bankruptcy IV: Pyrimidopyridazines (pages 193–222):
Chapter V Pyrimidooxazines and Pyrimidothiazines (pages 223–259):
Chapter VI Pyrimidotriazines (pages 261–304):

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Additional info for Chemistry of Heterocyclic Compounds: Fused Pyrimidines Part IV: Miscellaneous Fused Pyrimidines, Volume 24

Sample text

80Deazapurines were the expected products in this reaction. Although the reaction appears to be general, the yield did not exceed 50% for any example. Nitromalonaldehyde reacts with 6-aminouracils to give 6-nitropyrido[2,3dpyrimidines. 79The hydroxy group was not lost under these reaction conditions. Cyclization of 3-methyl-6-(benzylamino)uracil, 142 (R = CH2Ph), with 2,4pentanedione gave 3,5,7-trimethylpyrido[2,3-6)pyrimidin-2,~IH,3H)-dione, 143, with loss of the benzyl group, whereas 3-methyl-6-(phenylamino)uracil,142 (R = Ph), gave 8-phenyl-3,5,7-trimethylpyrido[2,3-6)pyrimidin-2,4(3H,8H)dione, HcowR 2.

Nitromalonaldehyde reacts with 6-aminouracils to give 6-nitropyrido[2,3dpyrimidines. 79The hydroxy group was not lost under these reaction conditions. Cyclization of 3-methyl-6-(benzylamino)uracil, 142 (R = CH2Ph), with 2,4pentanedione gave 3,5,7-trimethylpyrido[2,3-6)pyrimidin-2,~IH,3H)-dione, 143, with loss of the benzyl group, whereas 3-methyl-6-(phenylamino)uracil,142 (R = Ph), gave 8-phenyl-3,5,7-trimethylpyrido[2,3-6)pyrimidin-2,4(3H,8H)dione, HcowR 2. Methods of Synthesis of the Ring System '-N\ + XAN NIi2 I 23 R 135 136 0 0 0 R 137 R = H.

Treatment of 221 (R = Ph; R' = SCN; R" = OH or OEt) with polyfunctional nitriles also leads to pyrido[2,3-d]pyrimidines, 223. ' 51 Although this study focused primarily on reaction with trichloroacetonitrile, the implications are that other suitable nitriles could be successfully employed. The nitrile moiety can easily be replaced by carboxylic acid derivatives and serve as convenient precursors to pyrid0[2,3d]pyrimidines. 143-146 A series of 1,2-dihydro-2-thioxo-pyrido[2,3-d]pyrimidin4(3H)-ones, 225, was synthesized by this method.

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