Reaction of esters of 2-substituted 5-pyrimidinecarboxylic acids with hydrazine hydrate

The reaction of methyl esters of 2-substituted 5-pyrimidinecarboxylic acids with hydrazine hydrate at 0–5°C results in the nucleophilic substitution of readily eliminating groups (Cl, CH₃O, CH₃S) at the position 2 of the pyrimidine ring, and, on the boiling with the 80% aqueous solution of hydrazine hydrate, the reaction is accompanied by the formation of hydrazides. The dimethylamino group at thepposition 2 of the pyrimidine ring is not substituted by hydrazine.Vilnius University, Vilnius 2006, Lithuania Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1528–1530, November, 1999.     

Reaction of ethyl 9-thioacridonyl-10-acetate with hydrazine

The reaction of ethyl 9-thioacridonyl-10-acetate with hydrazine hydrate gives the corresponding ethyl hydrazonoacridonyl-10-acetate, which readily undergoes a reaction with aldehydes and on heating in DMF reacts with hydrazine hydrate to form 9-ylidenehydrazonoacridonyl-10-acetic acid hydrazide. The latter undergoes a condensation reaction with aldehydes to form ylidenehydrazides of acridonyl-10-acetic acid 9-ylidenehydrazones. The structures of these compounds have been confirmed by UV, IR, PMR, and mass spectrometry.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 525–527, April, 1989.     

Reaction of organylthiochloroacetylenes with hydrazine

Conclusions Alkylthiochloroacetylenes and arylthiochloroacetylenes react with hydrazine to give 3,6-bis(organylthiomethyl)-2,5-dihydro-1,2,4,5-tetrazines (II) and/or 3,5-bis(organylthiomethyl)-4-amino-1,2,4-triazoles depending on the nature of the substituent.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 960–961, April, 1989.     

Reaction of scandium trifluoride with hydrazine

ScF₃ reacts with anhydrous hydrazine yielding ScF₃·N₂H₄; upon heating the compound in inert atmosphere ScF₃ is regained. With hydrazine hydrate N₂H₅Sc(OH)F₃ is obtained with solid ScF₃; it decomposes to ScF₃ in two steps.     

Reaction of succinonitrile with anhydrous hydrazine

3,6-Dihydrazino-4,5-dihydropyridazine and 1,4,5,8-tetrahydrazino-pyridazino[1, 2-a]pyridazine were obtained by the reaction of succinonitrile with anhydrous hydrazine.     

Reaction of thiazolidinethiones with hydrazine hydrate

Thiazolidinethiones react with hydrazine hydrate to give bicyclic compounds with a bridge sulfur atom. The bicyclic structure of the reaction products is confirmed by data from¹H NMR and IR spectroscopy. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 171–172, January, 1998.     

Catalytic amination of 2-substituted pyridines with hydrazine derivatives

[reaction in text] Protected pyridylhydrazine derivatives were prepared in a one-step palladium-catalyzed amination reaction using chelating phosphine ligands. 2-Pyridyl chlorides, bromides, and triflates were effective electrophiles in these reactions. Di-tert-butyl hydrazodiformate was an excellent hydrazine substrate, and the resulting products were deprotected under mild conditions. Catalytic amination provides a direct route to protected bifunctional hydrazinopyridine linkers that are suitable for metal-bioconjugate syntheses.     

1, 9-substituted fluorenes

Syntheses of 3-chloropyridazino[4, 5, 6-m, l]fluorene and its 9-methyl and 9-chloro derivatives are described. Products in which a chlorine atom of these compounds is exchanged with NH₃, C₆H₅NH₂, NH₂ · NH₂, H₂O, C₆H₅NHNH₂, CH₃ONa, and compounds containing an active methylene group are prepared. Treatment of 3-hydrazinopyridazino[4, 5, 6-m, 1]fluorene and 3-hydrazino-9-methylpyridazino[4, 5, 6-m, 1]fluorene with alcoholic alkali and HgO give respectively pyridazino[4, 5, 6-m, 1]fluorene and 9-methylpyridazino[4, 5, 6-m, 1]fluorene, while 3-phenylhydrazinopyridazino[4, 5, 6-m, 1]fluorene is oxidized under the same conditions to 3-phenylazopyridazino[4, 5, 6-m, 1]fluorene.For Part II see [1].     

Reaction of β-aroylacrylic acids with 1-substituted 3,4-dihydroisoquinolines

The reactions of -aroylacrylic acids and their methyl esters with 1-methyl- and 1-benzyl-3,4-dihydroisoquinolines lead to the formation of -substituted -aroylpropionic acids and their esters, which undergo cyclization to benzopyrrocolinone derivatives.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 943–945, July, 1979.     

Synthesis of 5-substituted cyanofurans and their reaction with hydrazine

Based on the Schmidt reaction, a new method has been developed for the preparation of nitriles in furan series from the corresponding furfural derivatives. Depending on conditions, the reaction of 5-substituted cyanofurans with hydrazine leads to amidrazones, N-aminotriazoles, or 1,2,4,5-dihydrotetrazines.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 181–186, February, 1986.     

Reaction of some pyrylium salts with hydrazine

2,6-Diphenyl- and 2,6-di-tert-butylpyrylium salts react with excess hydrazine to give 1,2-diazeplne derivatives. Under the same conditions, 4-(1-methyl-3-indolyl)flavylium perchlorate forms 3-phenyl-5-(1-methyl-3-lndolyl)pyrazole.Translated from Khimiya Geterotsiklichesikikh Soedinenii, No. 1, pp. 45–48, January, 1973.     

Reaction of dialuric acid with hydrazine derivatives

In the condensation of dialuric, thiodialuric, and acetyldialuric acids with hydrazine derivatives, the ketone character of the CO group in the 2 position is manifested only in the case of acetyldialuric acid; the hydroxy or mercapto group in dialuric and thiodialuric acids is substituted to form 5-substituted derivatives of these acids.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 267–269, February, 1973.     

Reaction of tetracyanocyclopropyl ketones with hydrazine hydrate

The reaction of 2,2,3,3-tetracyanocyclopropyl ketones with hydrazine involved the addition at the carbonyl and cyano groups and resulted in the formation of previously unknown polycyclic systems whose common feature was the presence in the structure of a pyridazine ring. In the general case 3-substituted 6-amino-8-oxo-4,5,7-tptriazatricyclo[4.3.0.0^2.9]-non-3-ene-1,9-dicarbonitriles were obtained. The reaction with 3-pivaloylcyclopropane-1,1,2,2-tetracarbonitrile took another route with the opening of the three-membered ring and the formation of 3-amino-7a-tert-butyl-6-oxo-5,6,7,7a-tetrahydro-4aH-pyrrolo[2,3-c]pyridazine-4,5-dicarbonitrile.     

Reaction of 1-substituted 3-aminoquinolinediones with isocyanic and isothiocyanic acid

1-Substituted-3-aminoquinoline-2,4(1H,3H)-diones react with potassium cyanate or potassium thiocyanate in boiling acetic acid to give ureido- or thioureidooxindoles, spiro-oxindoles and dihydroimidazoquinolones. However, if the starting compounds are substituted with a benzyl group at position 3, a C-debenzylation proceeds to give imidazoquinolones. According to a proposed reaction mechanism, a molecular rearrangement of the primarily formed mono-substituted urea or thiourea takes place. All compounds were characterized by ¹H, ¹³C and IR spectroscopy and MS data.     

Reaction of 4-aryl-1,2,4-triazines with hydrazine

The action of hydrazine on 3,5-dioxo-4-aryl-2,3,4,5-tetrahydro-1,2,4-triazines gave 4-amino-3,5-dixo-2,3,4,5-tetrahydro-1,2,4-triazines. The intermediates of this reaction were isolated and shown to be α-ketoacidhydra-zide 4-arylsemicarbazones and not the α-ketoanilidecarbohydrazones. The realtive rates of cyclization of the latter isomeric derivatives provide a support for a proposed intermediates which were not isolated in the reaction of 3-mercapto and 3-methylmercapto-4-aryl-5-oxo-4,5-dihydro-1,2,4-triazines with hydrazine.     

Reaction of indolylpyrylium salts with some hydrazine derivatives

The reaction of 4-(3-indolyl)pyrylium salts with phenylhydrazine in alcohol gives 5-(3-indolyl)pyrazoles. The pyrylium salts react with acid hydrazides in refluxing dimethylformamide to give monohydrazones of the pseudobases of these salts (unsaturated 1,5-diketones).Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 184–186, February, 1972.     

Reaction of di(1′-iminoisoindolin-3-ylideneamino)arenes with hydrazine hydrochloride

It has been shown that the reaction of 1,3-di(1-iminoisoindolin-3ylideneamino)benzene and its derivatives and compounds related to them with hydrazine hydrate in dimethylformamide gives heterocyclic compounds. The structure of these compounds has been established, and their properties have been studied.