Chemistry of Heterocyclic Compounds: The Pyridazines,

This new quantity considerably updates the unique pyridazines quantity which used to be released in 1973. asserting the newest quantity within the profitable and widespread Chemistry of Heterocyclic Compounds Series.Content:
Chapter 1 basic Syntheses from Aliphatic or Carbocyclic Synthons (pages 1–58):
Chapter 2 basic Syntheses from different Heterocyclic structures (pages 59–130):
Chapter three Pyridazine, Alkylpyridazines, and Arylpyridazines (pages 131–176):
Chapter four Halogenopyridazines (H 219) (pages 177–250):
Chapter five Oxypyridazines (H 23) (pages 251–322):
Chapter 6 Thiopyridazines (H 755) (pages 323–342):
Chapter 7 Nitro?, Amino?, and similar Pyridazines (H 463, 629) (pages 343–386):
Chapter eight Pyridazinecarboxylic Acids and similar Derivatives (H353, 407) (pages 387–433):

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Extra info for Chemistry of Heterocyclic Compounds: The Pyridazines, Supplement 1, Volume 57

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259 .... R02C’ - - NH2 I (228) * rJ /N (229) 5-[~-(a-Hydrazino-O-nitrovinylamino)ethyl]thiomethyl-2-dimethy~aminomethylfuran and glyoxai gave 3-[~-(5-dimethylaminomethylfuran-2ylmethylthio)ethyl]amino-4-nitropyridazine (230) (PhCHzMe3NOH, H20-PhMe, 25”. 18 h: 80%). Also other examples. 4 Using Aliphatic Acids or Acyl Chlorides as C3-C4 Synthons Aliphatic acids or acyl chlorides have been used sparingly as C3-C4 synthons, although they do react satisfactorily, as illustrated in the following examples: 42 Primary Syntheses from Aliphatic or Carbocyclic Synthons 3-Phenylhydrazono-2,4-pentanedione(231) and choloroacetyl chloride gave 6-acetyl-4-chloro-5-methyl-2-phenyl-3(2~-pyridazinone (232) (NaH, THE 25".

741 1-Phenylbuta- 1,3-diene and diethyl azodicarboxylate gave diethyl 3-phenyl1,2,3,6-tetrahydro- 1,2-pyndazinedocarboxylate (PhH, reflux, N 2 , 4 h: 54%). 612,869. 1424. ”’ 2-Trimethylsiloxybuta- 1,3-diene and dimethyl azodicarboxylate gave dimethyl 4-trimethylsiloxy-1,2,3,6-tetrahydro-I ,2-pyridazinedicarboxylate (CHCI3. exothermic reaction; then 20°, 60min: 83%). 14” Methyl penta-2,4-dienoate and diethyl azodicarboxylate gave diethyl 3methoxycarbonyl-1,2,3;6-tetrahydro-1,2-pyridazinedicarboxylate (Et2 0 , trace hydrquinone, dark, 25”, 12 h; then reflux, 2 h: 84%).

576 1,2-Dibenzoyl-3-diphenylmethylcyclopropane(121) gave 4-diphenyl methyl-3,6-diphenylpyridazine (122) (NaOH, EtOH, reflux, 72 h: 65%). Ethyl 4-0x0-2-propionylvalerate (123) gave ethyl 3-ethyl-6-methyl-2,5dihydro-4-pyridazinecarboxylate(124) (EtOH, 25". 5 h: 55%) and thence the didehydro analogue ( H N 0 2 , HzO, 25", 1 h: 83%). 4-hexanedione) gave a dimer of 3,6-dimethyI-4,5dihydropyridazine (HzO, 30", 1 h; then 90". 3 1 8 . The dimer afforded From Two Synthons 23 monomeric 3-butyl-3,6-dimethyl-2,3,4,5-tetrahydropyridazine( 126) (LiBu, Et20, 30", 1 h: 50%).

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