By Richard H. Wiley
Content material:
Chapter 1 advent (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):
Read or Download Chemistry of Heterocyclic Compounds: Pyrazoles, Pyrazolines, Pyrazolidines, Indazoles and Condensed Rings, Volume 22 PDF
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Additional resources for Chemistry of Heterocyclic Compounds: Pyrazoles, Pyrazolines, Pyrazolidines, Indazoles and Condensed Rings, Volume 22
Sample text
Table 5 l i s t s examples of this reaction. Synthesis of pyrazoles from the reaction of aliphatic diazo derivatives with compounds having allenic s tr uctur es ( is o m e r s of the acetylenes) also s e e m s possible and has been observed with allene (1)and diazomethane. 510 (Eq. ) 26 CH,CeCCOOC,H, C,H,C=CCOOC,H, * Traces ** Or 5, 5'-dipyrazolyl 16 C,H,OCOCHN, C,H, COOC,H, C6H5 IH \H H COOC,H, C,H, CH,COOCH, CH, COOCH, COOC,H, H H CH,OH H H COOC,H, CHO CH, H R' CH2COOCzH, COOC,H, COOC,H, d COOC,H, C,H, COOC,H, C,H, C&, H H H H H CH,OH H H R" I COOC,H, COOC,H, COOC,H, COOC,H, COOC,H, COOC,H, COOC2H5 H H H H H H H H H H H H H R"' ""w "ANIPj H H CH=CCHO H H H H C,H, H CH-CCH20H f COC,H5 C=CH CHO H H H H CH,OH H H H R' H R Products: CH=CH 14 C2H50COCHN2 CH,OCOCH,C=CCOOCH, 15 C,H,OCOCHN, C,H,CECH 13 C,H,OCOCHN, 12 C,H,OCOCHN, 10 C,H,OCOCHN, 11 C,H,OCOCHN, CH3C=CCOOC,H5 C2H50COCH2C=CCOOC,H5 CH2N2 8 CH2N2 C,H,C-CCOOC,H, CHzNz 7 9 CH=CC,H, CH=CCOC,H, CH=CC=CH CH=CCHO CH,N, CH,N, 4 6 CH,N, 3 CH-CCH,OH CH,Nz CH,N, 2 CH=CH Acetylenic compound 5 CH2N2 1 N Diazo compound Reactants TABLE 5 * 94 535 270 372 495 754 862 94 278 94 535 195 **597 505 * 515 862 Ref.
61). 2 9 , 4 98,502 Sometimes migration of one of the geminal substituents to t h e neighboring nitrogen atom is observed30 (Eq. 62). Data for variously substituted isopyrazoles have established the following migratory aptitude s e r i e s : 4 9 8 p-dimethylanlinophenyl >> phenyl > p-bromophenyl > methyl. This is in agreement with a carbonium ion mechanism (Eq. 63). 49 Chapter 3 Table 15 lists some examples of this reaction. Isopyrazoles (6), p r e p a red from disubstituted p-diketones (5)and hydrazine, react with alkyl a n d arylalkyl halides to yield quaternary s a l t s (7) which in turn undergo pyrolysis losing one molecule of alkyl halide.
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.