By Richard H. Wiley
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 basic Reactions of Pyrazole Compounds (pages 65–80):
Chapter five Chemistry of Pyrazole Compounds (pages 81–174):
Chapter 6 advent (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 forms (pages 289–382):
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Additional info for Chemistry of Heterocyclic Compounds: Pyrazoles, Pyrazolines, Pyrazolidines, Indazoles and Condensed Rings, Volume 22
A. FROM ALIPHATIC DIAZO COMPOUNDS WITH ACETYLENE DERIVATIVES. with acetylene derivatives to yield pyrazoles. The reaction is usually c a r r i e d out a t room temperature in a convenient solvent. The most commonly used diaFo compounds a r e diazomethane and ethyl diazoacetate. Only a few others are used. In working with unstable diazocompounds, such as a-w-diazoparaffins, the technique of preparing the diazo compound "in situ" by reaction of i t s alkylene-bis-nitrosoacetylaminep r e c u r s o r with alkalies in p r e sence of the acetylene derivative862 is successful.
Arylhydrazines behave differently to f o r m 4-arylazopyraz 0 l e s , 3 ~probably ~ through osazones as intermediates. (Eq. ) R-c-c--N=w---C6n5 + ~NR’ \NH ‘-on i6H5 RT YN N=N-csn5 + I R‘ C6H5 (24) Intermediate formation of osazones is also probably involved in the conversion of 2-arylazo -1, 3 -diketones, 5 0 2-chloro - 1 , 3-dike tones,s S 2 2, 2-dichloro-1, 3-diketones750 1,1, 3, 3-tetrachloroacetone,1072 and di-isonitrosoacetone834 to 4 -arylazopyrazoles by reaction with a r y l hydrazine s.
34). 28 h3 (D 6 5 4 N H3C O E C C O O C H 3 J (C6H5),=C=N2 C6H5C-CCHO C6H5C-COOCH3 CH-CCOOCH, C6H5CrCCHO ,C=N2 C=N2 Acetylenic compound 5\C=N2 H,C/ (C6H5),=C=N2 ck H-C C6H5\ H3C' '6H5\ Diazo compound Reactants ~~ TABLE 6 C6H5 C6H5 C6H5 CH3 CH3 COOCH, CHO CHO COOCH, H COOCH3 502 502 502 502 502 502 OCH. 'fjH5 'CiH5 CGH5 COOCH, 502 Ref. eBr CGH, '15~5 C6H5 C6H5 'IjH5 C6H5 H C6H5 CH3 CH3 R"' R" R' ~/r "'rr R"' R Product: Chapter 3 The addition of nitro-vinyl compounds to the diazo group is modified by the strongly electron-attracting nature of the nitro group.