Synthesis of some functional derivatives ofo- andm-carboranes

Amides, amines, and alcohols were synthesized from 9-o- and 9-m-carboranecarboxylic chlorides. It follows from comparison of the¹H NMR spectra ofN,N-dimethyl-1-o- and-1-m-carboranecarboxamides andN,N-dimethyl-9-o- and -9-m-carboranecarboxamides that -bonding of the carborane polyhedron with the carbonyl group in 1-carboranyl dimethylamides is stronger than that in 9-carboranyl dimethylamides. Oxidation of 9-hydroxymethyl-m-carborune with pyridinium chlorochromate gives 9-m-carboranylmethyl 9-m-carboranecarboxylate.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 719–721, March, 1996.     

Synthesis of some cycloundecane derivatives from 1,5,9-cyclododecatriene

Summary Cycloundecanecarboxylic and cycloundecadienecarboxylic acids were synthesized from cis-trans-trans-1,5,9-cyclododecatriene.     

Synthesis and characterization of some nitrogen heterocycles from d-galactose derivatives

The tetrazoles 5-(6′-acetamido-6′-deoxy-1′,2′:3′,4′-di-O-isopropylidene-D-glycero-α-D-galactohexopyranos-6′-yl)tetrazole ( 1 ) and 5-(6′-acetamido-6′-deoxy-1′,2′:3′,4′–di-O-isopropylidene-L-glycero-α-D-galacto-hexopyranos-6′-yl)-tetrazole ( 2 ) were synthesized by the 1,3-dipolar cycloaddition reaction of the epimeric α-acetamidonitriles 5 and 6 , respectively, with sodium azide. Reaction of tetrazole 1 with acetic anhydride in the presence of pyridine afforded the N-acetyl-1,3,4-oxadiazole derivative 3 and the N-acetylacetamido-1,3,4-oxadiazole derivative 7 . The N-acetylacetamido-1,3,4-oxadiazole derivative ( 8 ) was isolated when the tetrazole 2 was allowed to react under the same conditions. The physical and spectroscopic data of the five new compounds 1, 2, 3, 7 and 8 are presented.     

Synthesis of some thiophene derivatives

The synthesis of thiopene derivatives from diacetylenic hydrocarbons has been described [1]. We have examined for the first time the reaction of diacetylenic diesters with hydrogen sulfide and with NaHS. The diacetylenic diesters react readily with hydrogen sulfide or NaHS in acetone at pH 9–10 to give 2,5-disubstituted thiopheries (see Table 1).Translated from Khimiya Geterotsiklicheskikh Soedinenii, Vol. 6, No. 5, pp. 713–714, May, 1970.     

Synthesis of some sym-triazole derivatives

3,5-Di(hydroxyalkyl) derivatives of 4-amino-1,2,4-triazole and the corresponding derivatives of 1,2,4-triazole obtained by diazotizing them are converted by reaction with SOCl₂ into the hydrochlorides of 4-amino-3,5-di(chloroalkyl)-1,2,4-triazoles and 3,5-di(chloroalkyl)-1, 2,4-triazoles. The dinitrate of 3,5-di(hydroxymethyl)-1,2,4-triazole has been prepared. When the cyanohydrazide of glycolic acid is heated with hydrazine hydrate, 4,5-diamino-3-hydroxymethyl-1, 2,4-triazole is formed.     

Synthesis of some phenanthridone derivatives

The alkylation of phenanthridone and some nuclear-substituted phenanthridones using sodium hydride in DMF/benzene is reported. Various 5-cyanoalkylphenanthridones were converted to further derivatives by either hydrolysis or reduction.     

Synthesis of some heptazine derivatives

Chemistry of Heterocyclic Compounds - New derivatives of heptazine were prepared from 2,5,8-trichloroheptazine by a Friedel–Crafts reaction and Pd-catalyzed amination. New...     

Synthesis of some thienopyrimidine derivatives

Thioxothienopyrimidinones, alkylthio- and arylalkylthiothienopyrimidinones, thienopyrimidinones, thienopyrimidines a thienopyrimidinedione and a thienotriazolo-pyrimidinone were prepared from 2-amino-3-carboethoxy-4,5-disubstituted thiophenes and 2-amino-3-cyano-4,5-disubstituted thiophenes via reactions with different reagents.     

Synthesis of some L-idose derivatives

The synthesis of 3-0-benzyl- and 3-0-mesyl-1,2-0-isopropylidene-β′-L-iodofuranose has been effected on the basis of the intramolecular nucleophilic exchange of a mesyloxy group at C₅ in derivatives of 1,2-0-isopropylidene-α-D-glucofuranose. It has been found that in a system of vicinal primary and secondary mesyloxy groups a selective replacement of the primary mesyloxy group by an acetyl group is possible. It has been shown in benzyl and mesyl ethers of 5,6-anhydro-1,2-0 -isopropylidene-β-L-idofuranose the opening of the oxide ring under conditions of acid hydrolysis with the retention of the isopropylidene group is possible.     

Synthesis of some crotonic derivatives

Summary Eight previously undescribed dicrotonic derivatives were synthesized. Synthesis was by the reaction of hexamethylene and 2,4-tolylene diisocyanates with crotonic acid, crotonamide, N-(hydroxymethyl)crotonamide, and N -2-hydroxyethylcrotonamide.     

Synthesis and structure of some thienopyrimidine derivatives

A series of substituted thieno[2,3-d]pyrimidines was synthesized starting from ethyl-2-amino-4-isopropylthiophene-3-carboxlate. Reaction of 2-hydrazino-5-isopropyl-thieno[2,3-d]pyrimidin-4(3H)-one and its 3-methyl analogue with different reagents afforded thieno[2,3-d]triazolo[4,3-a]pyrimidines and thieno[3,2-e]triazolo[4,3-a]pyrimidines, beside open chain derivatives. Correspondence: Atef A. Hamed, Department of Chemistry, Faculty of Science, Menoufia University, Shebin El Koam, Egypt.     

Synthesis of some novel sulfonyl ester derivatives derived from d-mannitol

The preparation of sulfonate-derivatives of d-mannitol i.e. 1,2:3,4-di-O-isopropylidene-3,4-di-O-p-toluenesulfonate-d-mannitol (3a), 1,2:3,4-di-O-isopropylidene-3,4-di-O-methanesulfonate-d-mannitol (3b), and 1, 2:3,4-di-O-isopropylidene-3,4-di-O-trifluoromethanesulfonate-d-mannitol (3c) is described. Full characterization and methodologies of these sulfonate-d-mannitol derivatives have been described as well.     

Synthesis and transformation of some thiourea derivatives

Reduction of a number of pyridylthiazolylketoximes gives amines, converted by p-ethoxyphenylisothiocyanate to the corresponding thioureas. It is shown that heating 3-pyridyl-,4-pyridyl-, and p-MeOC₆H₄-2-thiazolylmethylthiourea in dimethylformamide gives 7-substituted 5-mercaptoimidazo-[5,1-b]thiazoles, while heating substituted 2,4-dipyridylmethyl-and 2-pyridyl-2-tniazolylmethylthiourea gives 1-substituted 3-mercaptoimidazo[1,5-a]pyridines,     

Synthesis of some benzopyranocyclopentapyridine and pyranoacridine derivatives

Aminocoumarins react with ethyl cyclopentanone-and ethyl cyclohexanone-2-carboxylates to afford intermediates which on thermal cyclisation yield the title compounds.     

Synthesis of some benzofuronaphthyridines and benzofuronaphthyridine derivatives

The new benzofuro[2,3-b]naphthyridine ring system was prepared. 2,4-Dichloro-3-(o-methoxyphenyl)naphthyridines 3a and 3b were obtained by chlorination of hydroxynaphthyridinones 2a and 2b . Demethylation followed by cyclization of 3a and 3b afforded 11-chlorobenzofuro[2,3-b]naphthyridines 4a and 4b . Hydrogenolysis of these 11-chlorobenzofuronaphthyridines gave the parent benzofuro[2,3-b]naphthyridines 5a and 5b . The analog 4b was also converted to 11-methoxybenzofuro[2,3-b][1,8]naphthyridine ( 6 ).     

Synthesis and study of some imidazole derivatives

The preparation of esters of 4(5)-hydioxymethylimidazole with mono-, di-, and trichloroacetic acids is described. It has been established that in the reaction of imidazolylmethyl chloroacetate with diethanolamine, the latter is alkylated with the imidagolylmethyl part of the ester, giving rise to bis(2-hydroxyethyl)aminomethylimidazole.For communication II, see [1].     

Synthesis of new hetarylazoindole dyes from some 2-aminothiazole derivatives

A new series of heterocyclic disperse dyes were prepared by diazotization of some 2-aminothiazole derivatives and subsequent coupling with indole compounds. The dyes were characterized by UV-Vis, FT-IR, ¹H NMR, and mass spectra (LC-MS). Solvent effects on their visible absorption spectra were estimated. The color of the dyes is discussed with respect to the substituent therein. The effects of acids and bases on the visible absorption maxima of the dyes are also reported. Replacement of methyl group in the 4-position of the thiazole ring by phenyl group leads to red shift of the absorption maximum due to π-electron-donating properties of the phenyl group, while weak electron-withdrawing chlorine or bromine atom in the para-position of the phenyl group in the 2-amino-4-phenylthiazole fragment induce a small blue shift relative to 2-amino-4-phenylthiazole derivatives. Introduction of an electron-withdrawing 4-nitrophenylsulfonyl group into the thiazole ring produces bathochromic shift of the absorption maximum in all solvents. Published in Russian in Zhurnal Organicheskoi Khimii, 2008, Vol. 44, No. 4, pp. 592–599. The text was submitted by the authors in English.