By Richard H. Wiley
Chapter 1 creation (page 3):
Chapter 2 Tautomerism and Isomerism (pages 4–9):
Chapter three Syntheses of the Pyrazole Ring (pages 10–64):
Chapter four normal Reactions of Pyrazole Compounds (pages 65–80):
Chapter five Chemistry of Pyrazole Compounds (pages 81–174):
Chapter 6 creation (pages 177–179):
Chapter 7 Pyrazoline Syntheses (pages 180–208):
Chapter eight Chemistry of the Pyrazolines (pages 209–278):
Chapter nine Pyrazolidine Chemistry (pages 279–285):
Chapter 10 Indazoles and Condensed varieties (pages 289–382):
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Additional info for Chemistry of Heterocyclic Compounds: Pyrazoles, Pyrazolines, Pyrazolidines, Indazoles and Condensed Rings, Volume 22
At higher temperatures the differences between percentages of fission of N-alkyl and C-alkyl groups are less53 (Eq. 64). SYNTHESES BY REARRANGEMENT OF 4,4- OR OF 5,5DISUBSTITUTED PYRAZOLINES larz. Reduction by sodium and amyl alcohol of 4, 4-disubstituted-5-pyrazolones (1) affords the corresponding 5-hydroxypyrazolines (2) which, on treatment with acid, undergo rearrangement of a substituent from position 4 to 5 yielding pyrazoles ( 3 ) . 6 6 , 7 7 (Eq. ) ;>C-C-R’ 0 9lL LNY “ H2 I R” 1 2 3 (65) The reaction call be interpreted as a retro-pinacol rearrangement and it proceeds according to Eq.
Eq. ) Ci0OR CH2- ‘-NH, 1) 1 + TO-”’ CO-R“‘ -ROOC-CH, R”- CO-C-RN‘ \N/ I R’ 2 3 + R”uR ROOC I R‘ 4 (22) 19 Chapter 3 The only unsymmetrical diketone utilized up to now has been acetylbenzoyl (2, R” = C,H5, R”’ = CH,) in which the carbonyl adjacent to methyl is known to be the mor e reactive and f r o m which the 3-methylpyrazole was obtained. Table 2 l i s t s the known examples of this r e a c tion. Apparently the reaction is not applicable to a-ketoaldehydes. IV. SYNTHESES FROM 1,2,3-TRICARBONYL COMPOUNDS AND THEIR FUNCTIONAL DERIVATIVES WITH HYDRAZINE AND ITS DERWATIVES.
F o r instance, the product obtained by reacting desyl chloride (6) with S-methyldithiocarbohydrazide (7) in presence of sodium ethoxide is a stable thiadiazine (8) which, on heating with boiling glacial acetic acid, is converted to the pyrazole (9) with l oss of sulfur. (Eq. ) 22 Syntheses of the Pyrazole Ring 6 H 7 8 S-CH, + + s H 9 Alternatively, S-methyldithiocarbohydrazide (7) reacts with w-chloroacetophenone (10)to give a stable thiadiazine (11)which is converted, by boiling acetic acid, to the 4-mercaptopyrazole derivative (12)without l o s s of sulfur.
Chemistry of Heterocyclic Compounds: Pyrazoles, Pyrazolines, Pyrazolidines, Indazoles and Condensed Rings, Volume 22 by Richard H. Wiley