Synthesis of 7-methyl-6-(nitroimidazolyl)thiopurines

We have studied the reactions of 7-methyl-6-thiopurine with 5(4)-halo-4(5)-nitroimidazoles and 6-chloro-7-methylpurine with sodium and ammonium salts of 5-mercapto-4-nitroimidazoles. We have obtained a series of 7-methyl-6-(nitroimidazolyl)thiopurines not previously described in the literature.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 217–220, February, 2000.     

Synthesis of 2-Substituted 7-Methyl-6-(nitroimidazolyl)thiopurines

2-Substituted 7-methyl-6-(nitroimidazolyl)thiopurines have been synthesized by the reaction of 2-chloro(phenylamino, cycloalkylamino)-7-methyl-6-thiopurines with 5(4)-halo-4(5)-nitroimidazoles and the reaction of 2,6-dichloro-(6-chloro-2-dimethylamino)-7-methylpurines with sodium or ammonium salts of 5(4)-mercapto-4(5)-nitroimidazoles.     

Synthesis of 6-amino-2-(p-aminophenyl)-4-phenylquinazoline

A study was carried out on the amination of 6-chloro-2-arylquinazolines. The reaction of p-chlorophenyl- and p-nitrophenyl derivatives gives a mixture of mono- and diamination products with predominance of the monoamino products. The desired diamine was also obtained in the reduction of 6-amino-2-(p-nitrophenyl)-quinazoline.Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, 630090 Novosibirsk. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 547–550, April, 1995. Original article submitted November 24, 1994. Revision submitted March 10, 1995.     

Synthesis of 9-Substituted Derivatives of 6-(Nitroimidazolyl)thiopurines

The synthesis has been achieved of a series of 9-substituted derivatives of 6-(4-nitroimidazol-5-yl)- and 6-(5-nitroimidazol-4-yl)thiopurines by the reaction of 6-(nitroimidazolyl)thiopurines with alkyl and aralkyl halides, haloalcohols, haloacids and their esters, halo ketones, halo aldehyde acetals, and arylsulfonate esters using potassium carbonate in DMF.     

Synthesis and crystal structure of 6-amino-2-(p-aminophenyl)-4-phenylquinazoline

6-Amino-2-(p-aminophenyl)-4-phenylquinazoline (I), a monomer for the preparation of polymers, has been synthesized and studied by x-ray diffraction. The basic geometric characteristics of the molecule of compound (I) have been established-the small angle between the vectors along the C-NH₂ bonds [3.0 and 5.7° in the two symmetrically independent molecules (Ia) and (Ib), with distance between the N atoms of the amino groups 11.908 and 11.767(3) Å] and the coplanarity of the p-aminophenyl ring and the quinazoline rings (dihedral angle 1.0 and 3.3°)- and together with available data indicate the possibility of obtaining rigid-chain polymers based on compound (I).Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 2, pp. 412–416, February, 1990.     

Synthesis of 4-Acyl-2-amino-6-(arylsulfanyl)pyridine-3,5-dicarbonitriles

Russian Journal of Organic Chemistry - The reaction of 4-acyl-2-amino-6-chloropyridine-3,5-dicarbonitriles with aromatic thiols in 1,4-dioxane in the presence of triethylamine led to the formation...     

Synthesis of 10-propargylfolic acid from 2-amino-6-(bromomethyl)-4(1h)-pteridinone

6-(Bromomethyl)-2,4-pteridinediamine hydrobromide (1) is readily converted to 2-amino-6-(bromomethyl)-4(1H)-pteridinone hydrobromide (2) by treatment with 48% hydrobromic acid. Compound 2 is of interest for direct attachment of the (2-amino-3,4-dihydro-4-oxo-6-pteridinyl)methyl group to appropriate side-chain precursors of analogues of folic acid, particularly those bearing functional groups incompatible with conditions required for hydrolytic deamination of the corresponding 2,4-diaminopteridine analogues. An example of the use of 2 in this connection is demonstrated through synthesis of 10-propargylfolic acid.     

Synthesis of 2-amino-5-(N-azolyl)pyrans

N. D. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Moscow. Translated from Khimiya Geterotsiklicheskikh. No. 12, pp, 1699–1700, December, 1995. Original article submitted November 24, 1995     

Synthesis of 2-R-6-R′-4-(5-amino-1,3,4-oxadiazol-2-yl)quinolines

Russian Journal of Organic Chemistry -     

Synthesis of 5-amino-6-(nitro-NNO-azoxy)-1,2,3,4-tetrazine 1,3-dioxide

Russian Chemical Bulletin - A reaction of 5-amino-6-(tert-butyl-NNO-azoxy)-1,2,3,4-tetrazine 1,3-dioxide with nitronium tetrafluoroborate affords 5-amino-6-(nitro-NNO-azoxy)-1,2,3,4-tetrazine...     

Synthesis of 3-(2-amino-2-carboxyethyl)-2-carboxy-7-chlorobenzofuran

Two methods for the synthesis of 3-(2-amino-2-carboxyethyl)-2-carboxy-7-chlorobenzofuran are proposed.Faculty of Chemistry, N. Copernicus University, Torun 87–100, Poland. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1048–1050, August, 1997.     

Synthesis of 3-amino-4-(thienyl-2)furazan

3-Amino-4-(thienyl-2)furazan (3) has been synthesized from 2-acetylthiophene (4) by several routes. Nitrosation of 4, followed by oximation of the resulting oxime salt 5, gave a 6:1 mixture of the E,E and E,Z isomers of thienylglyoxime (1). Estimation of differences and analogies of these isomers' reactivity have been carried out. Oxidation and dehydration of 1 gave furoxan 11 and furazan 2, respectively. Conversion of 2, 12, 13, and 11a, b into the target amine 3 by base-promoted reaction with hydroxylamine has been reported. © 1997 John Wiley & Sons, Inc.     

Synthesis of 2-amino-3-(ω-aminoalkyl)indoles

2-Amino-3-(-phthalimidoalkyl)indoles have been obtained by the rearrangement of -phthalimido acid -phenylhydrazides under the action of POCl₃. The possibility has been studied of eliminating the phthalyl protective group from these compounds and a convenient method has been developed for obtaining 2-amino-3-(-aminoalkyl)indole dihydrochlorides. The behavior of the 2-amino-3-(-phthalimidoalkyl) indoles in alkylation reactions has been investigated.Deceased.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 484–488, April, 1980.     

4-(1-Adamantylamino)-2-amino-6-methoxy-5-nitrosopyrimidine

The title compound, C₁₅H₂₁N₅O₂, lies on a crystallographic mirror plane and is hydrogen bonded to neighbouring mol­ecules by infinite chains formed by combinations of strong N—H⃛N and soft C—H⃛O hydrogen bonds. The pyrimidine moiety shows extensive delocalization.     

(S)-2-氨基-1,1-二苯基-1-丙醇的合成

以L-丙氨酸为原料,经苄基保护、格氏反应和脱苄基反应合成了(S)-2-氨基-1,1-二苯基-1-丙醇,总收率48.1%,其结构经1H NMR,IR,EI-MS和元素分析表征。     

Synthesis of 2-amino-3-benzyl-5-(p-hydroxyphenyl)pyrazine

2-Amino-3-benzyl-5-(p-hydroxyphenyl)pyrazine (2), a precursor of Watasenia preluciferin (coelenterazine) (1), is widely distributed in marine bioluminescent animals. It was prepared from p-hydroxyphenylglyoxal aldoxime (5) in two steps; by condensation with or-aminophenylpropiononitrile in the presence of TiCl4 in pyridine, followed by reduction of the resulting N-oxide (6) with Zn-AcOH in CH2Cl2 and produced 2, with an 89% overall yield. This procedure was linked with the facile one-step preluciferin synthesis reported in the previous paper. Thus, Watasenia preluciferin (1), frequently required for various chemiluminescent and bioluminescent studies, was coveniently synthesized in three steps from 5, with a 56% overall yield, overcoming the difficulty of obtaining it from natural sources.