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New PDF release: Chemistry of Heterocyclic Compounds: The Pyridazines,

ISBN-10: 0470187972

ISBN-13: 9780470187975

ISBN-10: 0471251372

ISBN-13: 9780471251378

This new quantity considerably updates the unique pyridazines quantity which used to be released in 1973. asserting the newest quantity within the winning and well known Chemistry of Heterocyclic Compounds Series.Content:
Chapter 1 fundamental Syntheses from Aliphatic or Carbocyclic Synthons (pages 1–58):
Chapter 2 fundamental 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 comparable Derivatives (H353, 407) (pages 387–433):

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

Example text

0 24 Primary Syntheses from Aliphatic or Carbocyclic Synthons 3-Benzoyl-2-benzyl-2-hydroxypropionic acid (131) gave 4-benzyl-6-phenyl3(2H)-pyridazinone (EtOH, reflux, 3 h: 71 %; note dehydrative oxidation). 5-dihydro3(2H)-pyridazinone (K salt, H20, reflux, 2h: 88%) and thence 6-mnitrophenyI-3(2H)-pyridazinone (Brr. AcOH, 70°, 2 h: 86%). I M 8 4-Cyano-4-morpholino-4-(5-trifluoromethylthien-3-yl)butyric acid (134) [ = 3-(5-trifluoromethylthen-3-oyl)propionic acid] gave 6-(5-trifluoromethylthien-3-yl)-4,5-dihydro-3(2H)-pyridazinone(EtOH, reflux, 8 h: 76%) and then the didehydro analogue (Se02, (EtOCH2CH2)20, reflux, 20 min: 9 I 8).

364 Ethyl 4,4-dicyano-3-methyl-2-phenylhydrazonobut-3-enoate (made in situ) 1 -pheny1- 1,6-dihydr0-3-pyridazinegave ethyl 5-cyano-6-imino-4-methylcarboxylate (weakly basic, 30 min: 66%). '" NtI From a Single Six-Atom Synthon PhHC=NHNOCC’ II 13 CN NIIPh I Me+ N I CO2Et (64) ,CN X Cyclization in Acid Ethyl 4-benzylidenehydrazinocarbony1-4-cyano-3-methyI-2-phenyl hydrazonobut-3-enoate (64) gave ethyl 5-benzylidenehydrazinocarbonyl-6-imino4-methyl- 1-pheny1- 1,6-dihydro-3-pyridazinecarbox y late (65) (AcOH, HCI, reflux, 2 h: 75%).

1762. 1763,1833. 1871, 1875. 1895. 1959. 1965. 2096 With Appropriate Keto Esters or Amides Ethyl 3-p-nitrobenzoy llactate (135) gave 6-p-nitrophenyl-3( ZH)-pyridazinone (136) (BuOH, reflux, 8 h: 88%; note dehydrative oxidation). 2HC1, EtOH, reflux, 18 h: 53; note use of hydrazine salt to avoid hydrazinolysis of the surviving ester grouping). 1767 Ethyl levulinate (139, R = H) gave 6-methyl-4,5-dihydro-3(2H)-pyridazinone (140, R=H) (EtOH, reflux, 4h: 90%);1550likewise, ethyl 2hydroxylevulinate (139, R = OH) gave 4-hydroxy-6-methyl-4,5-dihydro* 3(2H)-pyridazinone (140, R =OH) (EtOH, 25”, 2 h: 88%), which readily underwent dehydrative oxidation to give 6-methyl-3(2H)-pyridazinone (EtOH-HCI, reflux, 2 h: 75%).

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


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