Reactions of furan derivatives with aliphatic carbonyl compounds in acid medium

Sixteen new derivatives of the furan and of the 1,1-difurylmethane series were synthesized by the reactions of furan, 2-methylfuran, 2-(3′-acetoxypropyl)furan, 2-(3′-butyl)furan, 1-cyclopropyl-2-αfurylcyclopropane, and 1,1-difurylethane with saturated and α, β-unsaturated aliphatic carbonyl compounds in acid medium.     

Reactions of furan derivatives with aliphatic carbonyl compounds in acid medium

Sixteen new derivatives of the furan and of the 1,1-difurylmethane series were synthesized by the reactions of furan, 2-methylfuran, 2-(3-acetoxypropyl)furan, 2-(3-butyl)furan, 1-cyclopropyl-2-furylcyclopropane, and 1,1-difurylethane with saturated and , -unsaturated aliphatic carbonyl compounds in acid medium.     

Reactions of some dicarbonyl compounds

The reactions of some halogeno keto-esters and the sodio derivatives of β-dicarbonyl compounds have been investigated.     

Reactions ofP-cyanospirophosphoranes with derivatives of phosphorous acid

5-Cyano-2,3,7,8-tetramethyl-1,4,6,9-trioxathia-5-phosphaspiro[4.4]nonane reacts with some chlorophosphites and amidophosphites to give the correspondingP ^III-cyano derivatives.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1669–1670, September, 1994.     

Reactions of some new thienothiophene derivatives

Facile and convenient syntheses of bisdimethylthieno[2,3-b]thiophen-2,5-diyl bis(oxazole-2-amine), bis(1H-imidazol-2-amine), bis((3a)-H-indole),[1,2-a]pyrimidine), bis(1H-imidazo[1,2-b][1,2,4]triazole) and bis(9H-benzo[d]imidazo[1,2-a]imidazole) derivatives incorporating a thieno[2,3-b]thiophene moiety from the versatile and readily accessible 1,1'(3,4-dimethylthieno[2,3-b]thiophene-2,5-diyl)-bis(2-bromo-ethanone) (1) are described.     

Reactions of cyclic sulfur ylides with some carbonyl compounds

The reaction of a six‐membered sulfonium ylide 5 with aldehydes or ketones afforded the oxirane derivatives 6a–d as a mixture of cis and trans isomers in excellent yields. In addition, the same reactions, using five‐ or six‐membered cyclic oxosulfonium ylides 7 and 11 , gave the corresponding oxirane derivatives in good yields. Moreover, the reaction of 11 with two equimolar amounts of base and 4‐hexen‐3‐one afforded the cyclooctene oxide derivative 16 with high stereoselectivity in 59% yield via a sequential Michael–Michael‐type addition of the ylide and the resulting enolate ion followed by an intramolecular Corey–Chaykovsky reaction. © 2002 Wiley Periodicals, Inc. Heteroatom Chem 13:216–222, 2002; Published online in Wiley Interscience (www.interscience.wiley.com). DOI 10.1002/hc.10022     

Reactions of derivatives of sulfamic acid with epoxides

1,3-Diamino-2-propanols were prepared in high yields by reactions of potassium or sodium 3-chloro-2-hydroxypropylsulfamates with amines followed by acid hydrolysis of the 3-amino-2-hydroxypropylsulfamates that formed.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2693–2697, November, 1996.     

Reactions of highly electrophilic polyfluoro unsaturated compounds with pyrazole derivatives

Pyrazole derivatives were hydroxyalkylated at the C⁴ atom by hexafluoroacetate and methyl trifluoropyruvate. The products of the hydroxyalkylation were dehydrated to the corresponding alkylidene derivatives which were reacted with nucleophiles. Dicyanoethylenes, obtained from polyfluorocarbonyl compounds, alkylated pyrazol-5-ones with the formation of pyrazolopyran derivatives.A. N. Nesmeyanov Institute for Organometallic Compounds, Russian Academy of Sciences, 117813 Moscow. Translated fromIzvestiya Akademii Nauk, Seriya Khimicheskaya, No. 11, pp. 2617–2623, November, 1992.     

Anthranilic acid hydrazide in the synthesis of fused polycyclic compounds with quinazoline moieties

A modified procedure was developed for the synthesis of 5,6,7,8,13,13a-hexahydrophthalazino[1,2-b]quinazoline-5,8-dione and 6-amino-5,6,6a,11-tetrahydroisoindolo[2,1-a]quinazoline-5,11-dione from o-formylbenzoic acid and anthranilic acid hydrazide. The mechanism of the transformation is suggested, some reactions were studied, and new derivatives of these compounds were synthesized. Anthranilic acid hydrazide was used in the novel synthesis of 5-substituted phthalazino[1,2-b]quinazolin-8-one derivatives. The possible reaction mechanism is discussed. 5,6,7,8-Tetrahydrophthalazino[1,2-b]quinazoline-5,8-dione and 5-phenylphthalazino[2,1-b]quinazolin-8-one were studied by X-ray diffraction.     

1,2,3,4-Tetrahydropyrimidines and some other compounds based on propiolic acid derivatives

The reactions of ethyl propiolate and propiolamide with methylene and benzaldehyde and anisaldehyde in an acidic medium, in which the corresponding 2-oxo-1,2,3,4-tetrahydropyrimidines and 1,4-dihydropyridines or a 3,4-dihydropyrimidine derivative are formed, were studied.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 529–531, April, 1984.     

Reactions of some 4-dicyanomethylenepyran derivatives with malononitrile and hydrazines

4-Dicyanomethylene-2-phenyl-4H-benzo[b]pyran, the corresponding thiapyran, and 4-dicyanomethylene-2,6-diphenyl-4H-pyran react with malononilrile under basic conditions to give 5-amino-4-cyano-2-phenylbenzo[b]pyrano[4,3,2-de] [1,6]naphthyridine, the corresponding thia-pyranonaphthyridine derivative, and 5-amino-6-cyano-2,8-diphenylpyrano[4,3,2-de] [1,6]naphthyridine, respectively. Certain other related reactions were studied in the course of investigating the above reactions. Hydrazine hydrate and 4-dicyanomethylene-2-phenyl-4H-benzo[b]pyran gave 5-(2-hydroxyphenyl)-3-phenylpyrazole, and phenylhydrazine gave 5-(2-hydroxyphenyl)-1,3-diphenylpyrazole.     

Studies on cardiotonic agents. I. Synthesis of some quinazoline derivatives

A series of quinazoline derivatives with various 4-heterocyclylpiperidino groups at the 4-position was synthesized and tested for cardiotonic activity in anesthetized dogs. Among them, several 6,7-dimethoxyquinazoline derivatives showed potent cardiotonic activity.