Synthetic studies of hydrazine and guanidine: derivatives of 5-pyrazoles

1968 ◽  
Vol 46 (7) ◽  
pp. 1079-1091 ◽  
Author(s):  
Joseph Zauhar ◽  
Benoit F. Ladouceur
Keyword(s):  
Hydrazine Hydrate ◽  
Dimethyl Formamide ◽  
Condensation Products ◽  
Guanidine Derivatives ◽  
Synthetic Studies ◽  
Derivatives Of ◽  
Related Compounds ◽  
Reaction Schemes

The reactions of several substituted 5-chloropyrazoles with hydrazine hydrate and guanidine, respectively, were investigated in ethanol and dimethyl formamide media. In certain cases, only SN2 reactions occurred, while in others the 5-hydrazino- and 5-guanidopyrazoles reacted still further to yield related compounds with two pyrazole rings. On the basis of the intermediates and the different condensation products isolated, reaction schemes are proposed for the reactions discussed.

scholarly journals Peculiarities of the reactions of a,b-unsaturated g-bromoketones with hydrazine derivatives

2018 ◽  
Vol 6 (1) ◽  
pp. 56-66 ◽  
Author(s):  
Lyudmyla Potikha
Keyword(s):  
Hydrazine Hydrate ◽  
Aliphatic Ketone ◽  
Reaction Conditions ◽  
Hydrazine Derivatives ◽  
Michael Type Addition ◽  
Derivatives Of ◽  
Reaction Result ◽  
Reaction Schemes

The reaction result of a,b-unsaturated g-bromoketones with hydrazines depends on the structure of the reagents. Reaction with hydrazine hydrate leads to the mixture of 3,5- di(R)pyridazine, 3,6-di(R)pyridazine and 2,4-di(R)-1H-pyrrol-1-amine derivatives. The formation of three types of products is due to the structure of the unsaturated aliphatic ketone. Two competing reaction schemes of ketones with hydrazines are considered, which include condensation or Michael-type addition in the first stage. The main products of the reactions of halogen-substituted derivatives of g-bromodipnone with arylhydrazines are 1,3,5-triaryl-1,6-dihydropyridazines, which easily form aromatic salts under reaction conditions (when heated in EtOH).

ChemInform Abstract: Regioselective Bromination of Methoxy Derivatives of Ethyl Indole-2- carboxylate (Synthetic Studies of Indoles and Related Compounds. Part 30.).

ChemInform ◽  
2010 ◽  
Vol 24 (9) ◽  
pp. no-no
Author(s):  
M. TANI ◽  
H. IKEGAMI ◽  
M. TASHIRO ◽  
T. HIURA ◽  
H. TSUKIOKA ◽  
...  
Keyword(s):  
Synthetic Studies ◽  
Derivatives Of ◽  
Related Compounds

Regioselective Bromination of Methoxy Derivatives of Ethyl Indole-2-carboxylate [Synthetic Studies of Indoles and Related Compounds. XXX]

Heterocycles ◽  
1992 ◽  
Vol 34 (12) ◽  
pp. 2349 ◽  
Author(s):  
Yasuoki Murakami ◽  
Masanobu Tani ◽  
Hiroyo Ikegami ◽  
Mayumi Tashiro ◽  
Tetsuji Hiura ◽  
...  
Keyword(s):  
Synthetic Studies ◽  
Derivatives Of ◽  
Related Compounds

Synthesis of 5,7-dihydroxynaphthoquinone derivatives and their reactions with nucleophiles: Nitration of 2,3-dimethylnaphthalene and subsequent transformations

1976 ◽  
Vol 29 (10) ◽  
pp. 2247 ◽  
Author(s):  
HJ Banks ◽  
DW Cameron ◽  
MJ Crossley ◽  
EL Samuel
Keyword(s):  
Unusual Reaction ◽  
Nitro Derivatives ◽  
Reactions With Nucleophiles ◽  
Derivatives Of ◽  
Related Compounds ◽  
Benzenoid Ring

5,7-Dihydroxy-2,3-dimethyl-l,4-naphthoquinone (5) and related compounds have been synthesized. The quinone affords an accessible substrate for studying an unusual reaction with nucleophiles, which involves attack at the 8-position, i.e. at the benzenoid ring. An unsuccessful approach to (5) has led to tri- and tetra-nitro derivatives of 2,3-dimethylnaphthalene. Reduction of the former and subsequent conversions have given aminonaphthoquinone and perimidinone derivatives.

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