Benzo[1,2-d: 3, 4-d′] diimidazole derivatives

It is shown that; in agreement with the results of molecular orbital calculations, hydroxylation to form the corresponding imidazolones (III, IV and V) occurs by the action of anhydrous potassium hydroxide on benzo[1,2-d: 3,4-d]diimidazole derivatives (I and II). However, these compounds do not undergo direct animation. 2-Amino-3,6-dimethyl- and 2-amino-3, 6,7-trimethylbenzo[1,2-d: 3,4-d]diimidazoles are obtained by the cyclization of the appropriate diamine of the benzimidazole series (VIa, b) with cyanogen bromide.See [1] for communication I.Translated from Khimiya Geterotsiklicheskikh Soedinenu, No. 8, pp. 1132–1135, August, 1971.     

Synthesis of 1H-[1]benzothiopyrano[3,4-d]imidazol-4-ones

By the condensation of 3,4-diaminothiocoumarins containing primary or secondary amino groups in position 4, with formic and acetic acids (or acetic anhydrides), a number of 1H-[1]benzothiopyrano[3,4-d]imidazol-4-ones and their 2-methyl derivatives have been synthesized; the latter have also been obtained from the corresponding 3-monoacetylamino-4-aminothiocoumarins. By the acetylation of 3-4-diaminothiocoumarins with tertiary amino groups in positions 4 their 3-diacetyl derivative has been obtained, and these, under the action of bases, have been converted into 3-N-acetyl derivatives. The structures of the compounds synthesized have been confirmed by IR, PMR, and mass spectroscopy.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 479–483, April, 1980.     

Synthesis of 1-phenyi-1H-tetrazolo[4,5-d]tetrazole and 5-aryl-1-(4-bromophenyl)-1,2,4-triazolo[4,3-d]tetrazoles

l-Phenyl-lH-tetrazol-5-yIhydrazine (2) was reacted with nitrous acid to yield 1-phenyl-lH-tetrazolo[4,5-d]tetrazole (3). l-Arylidene-2-(l-phenyl-lH-tetrazol-5-yl)hydrazines (4) were generally reactive towards electrophilic reagents. When treated with bromine in acetic acid, 4 yielded mixtures of 1-arylidene-2-[1-(4-bromophenyl)-lH-tetrazol-5-yl]hydrazines (5a-d) and 2-[1-(4-bromophenyl)-lH-tetrazol-5-yl]hydrazidic bromides (6a-d). Solvolysis of 6a-d in aqueous acetone yielded 5-aryl-1-(4-bromophenyl)-1,2,4-triazolo[4,3-d]tetrazoles (7a-d). The structures of the synthesized compounds were confirmed on the basis of elemental analysis, IR and ¹H NMR data.     

Pyrrolo[1,2-d]triazines-1,2,4. II. Etude des pyrrolo[1,2-d]triazinones-1 et -4

The synthesis of 1,2-dihydro-1-oxopyrrolo[1,2-d]-1,2,4-triazines was achieved by rearrangement of 2-pyrrolyloxadiazoles under alkaline conditions or by cyclisation of pyrrole N-ethoxymethylidene hydrazides. The cyclisation of the N-carbethoxy hydrazone of the pyrrole-2-carboxaldehyde gave the 3,4-dihydro-4-oxopyrrolo[1,2-d]-1,2,4-triazine. Electrophilic substitution reactions of the 1- and 4-pyrrolotriazinones were made either on the lactam nitrogen with methyl sulphate, benzyl chloride and monochloroacetic acid or on the pyrrole ring with bromine and nitric acid. The structure of the derivatives was determined by ¹H nmr.     

Selenium heterocycles. XXXIX. Synthesis of thieno[3, 4-d]thiazole,thieno[3, 4-d]selenazole,selenolo[3, 4-d]thiazole and selenolo[3, 4-d]selenazole

Starting from readily available methyl 2-substituted4-methyl-5-thiazolyl ketone and methyl 4-methyl-2-phenyl-5-selenazolyl ketone, thieno[3, 4-d]thiazole, thieno[3, 4-d]selenazole, selenolo[3, 4-d]thiazole and selenolo[3, 4-d]selenazole were prepared. The structures of all compounds were confirmed by analytical and spectroscopic methods.     

Synthesis of functionalized 2,3-dihydrothieno[2,3-d]pyrimidin-4(1H)-ones and their recyclization to 2,3-dihydrothieno[3,4-d]pyrimidin-4(1H)-ones

By the reaction of 6-aryl(alkyl)amino-5-cyano-2,3-dihydro-1,3-thiazin-4(10)-ones with α-halogenoketones in the presence of triethylamine, 2,3-dihydrothieno[2,3-d]pyrimidin-4(1H)-ones have been synthesized and their acid-catalyzed recyclization to 2,3-dihydrothieno[3,4-d]pyrimidin-4(1H)-ones has been found and studied. © 2006 Wiley Periodicals, Inc. Heteroatom Chem 17:104–111, 2006; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20181     

Quinazolines et benzodiazépines-1, 4. LVI. Oxadiazolo-1, 2, 4[4, 5-d] benzodiazépines-1, 4: synthése et passage aux oxazolo [3, 2-d] benzodiazépines-1, 4

The tricyclic derivatives 4–14 can be prepared by 1, 3-dipolarcycloaddition of the appropriate nitrile oxides on the corresponding 1, 4-benzodiazepines. NaBH⁴ reduction of the esters 12–14 was found to proceed very readily; starting from 13 it is possible, by proper reaction conditions, to get in good yield either the monoalcohol 19 or the aminodiol 20 . The alcohols 19 and 23 undergo an acid-catalysed rearrangement which produces the amidoximes 24 and 26 . The determination of the structure of 24 by X-ray diffraction analysis is also presented.     

1,3-二苄基-4-(4-甲氧羰基丁基)-噻吩并[3,4-d]-咪唑-2-酮的合成

1,3-二苄基-4-(4-甲氧羰基丁基)-噻吩并[3,4-d]-咪唑-2-酮(Ⅰ)是合成生物素的一个关键中间体.在超声波促进下,用低价钛试剂对(4 aR)-1,3-二苄基-4-(1-己二酸单甲酯酰基硫甲基)-咪唑-2,5-二酮(Ⅱ)进行还原偶联,即生成1,3-二苄基-4-(4-甲氧羰基丁基)-噻吩并[3,4-d]咪唑-2-酮(Ⅰ).超声反应1.5 h,收率71%.     

Synthèse des pyrido[2,3-d] el [3,2-d] -s-triazolo[3,4-f] pyrimidines el de (pyrazolyl-1')-4 pyrido[2,3-d] et [3,2-d] pyrimidines

The synthesis of two new heterocycles is described: pyrido-[2,3-d]-.s-triazolo[ 3,4-f] pyrimidine and pyrido[3,2-d]-.s-triayzolo-[3,4-f] pyrimidine. 4-[I'-Pyrazolyl]pyrido[2,3-d]pyrimidines and 4-[1′-pyrazoly1] pyrido[ 3,2-d] pyrimidine are obtained by the action of 4-hydrazinopyrido[2,3-d]pyrimidine and 4-hydrazinopyrido-[3,2-d]pyrimidine with several β-diketones.     

Synthesis and properties of substituted 1-aryl-1,4-dihydro-4-oxopyrido[2,3-d]-pyrimidines

The reaction of 2-arylamno-6-methylnicotinonitriles with acetic anhydride or benzoyl chloride gives N-acyl-2-arylamino-6-methylnicotinonitriles. Upon treatment with hydrogen chloride in anhydrous ethanol, these products are converted to 2-substituted 1-aryl-1,4-dihydro-7-methyl-4-oxopyrido[2,3-d]pyrimidines. Heating amides of 2-aryl-amino-6-methylnicotinic acids or 1-aryl-2,7-dimethyl-1,4-dihydro-4-oxopyrido[2,3-d]-pyrimidines at reflux with acetic anhydride in the presence of anhydrous sodium acetate gives 1-aryl-2-acetonyl-7-methyl-1,4-dihydro-4-oxopyrido[2,3-d]pyrimidines.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 114–116, January, 1985.     

Über 4-Ureidooctahydropyrano[4,3-d]pyrimidinone

Zusammenfassung 5,6-Dihydro-2H-pyran-3-aldehyde reagieren mit Harnstoff zu 4-ureidooctahydropyrano[4,3-d]pyrimidin-2-ones. Einwirkung von Säure führt das 4-Ureidooctahydropyrano[4,3-d]pyrimidin-2-on in das 4-(2-Hydroxyäthyl)-hexahydropyrimido[4,5-d]pyrimidin-2,7-dion über.

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Heterocycles, XVIII: 4-Ureido-octahydropyrano[4,3-d]-pyrimidinones

5,6-Dihydro-2H-pyran-3-aldehydes react with urea to give 4-ureidooctahydropyrano[4,3-d]pyrimidin-2-ones. 4-Ureidooctahydropyrano[4,3-d]pyrimidin-2-one is cleaved by HCl to 4-(2-hydroxyethyl)-hexahydropyrimido[4,5-d]pyrimidin-2,7-dione.

     

Synthese von 4H-Pyrano[2,3-d]pyrimidinen

Summary Good yields of substituted 5-(5R-2-furyl)-4H-pyrano[2,3-d]pyrimidines4 were obtained in the reaction of 2-ethoxymethyleneamino-3-cyano-4H-pyranes2 with ammonia. Compounds2 were prepared by the condensation of the starting 2-amino-5-acetyl-3-cyano-6-methyl-4H-pyranes1 with ethyl orthoformate. Spectral properties of the bicyclic system4 in relation to compounds3 are discussed.

     

3,6-二烷硫基-1-苯基-吡唑并[3,4-d]嘧啶-4-酮衍生物的合成与除草活性

通过3-甲硫基-1-苯基-吡唑并[3,4-d]嘧啶-6-硫酮和卤代烃RX(BrR'Br)亲核取代反应合成了16种标题化合物,其结构使用元素分析、IR,1H NMR及LC-MS进行了表征.初步的生物活性测试表明,部分化合物对单、双子叶植物根的生长具有优异的抑制作用.     

Bromination of 4-hydroxypyrazolo[3,4-d]pyrimidines

The bromination of 4-hydroxypyrazolo[3,4-d] pyrimidine and its N-methyl analogs leads to the corresponding 3-bromo derivatives. Inhibition of the reaction by 4-hydroxypyrazolo[3,4-d] pyrimidine was observed during a study of the bromination kinetics; this is explained by complexing.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 397–402, March, 1978.The authors thank V. V. Ogorodnikova for recording the UV spectra and F. S. Shub for assistance in discussion of the results of the kinetic experiments.     

Synthesis and properties of 2-substituted 1-aryl-4-oxo-1,4-dihydropyrido[2,3-d]pyrimidines

Cyclization of 2-(N-acetyl-N-arylamino)nicotinonitriles in the presence of dry HCl gave 1-aryl-2-methyl-4-oxo-1,4-dihydropyrido[2,3-d]pyrimidines. It was shown that they are acylated by acetic anhydride, aroyl chlorides, and phenyl isocyanate at the methyl group and that with benzaldehyde they give styryl derivatives. It was determined by UV, IR, and NMR spectra that 2-acetonyl, 2-phenacyl, and 2-(N-phenylcarbamoylmethyl) derivatives of 1-aryl-4-oxo-1,4-dihydropyrido[2,3-d]pyrimidines exist in enaminocarbonyl and imino enol forms with strong chelate-type intramolecular hydrogen bonding.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1397–1401, October, 1991.     

Synthesis and properties of 1-aryl-2,5,7-trimethyl-4-oxo-1,4-dihydropyrido[2,3-d]pyrimidines

1-Aryl-2,5,7-trimethyl-4-oxo-1,4-dihydropyrido[2,3-d]pyrimidines are formed from the cyclization of N-acetyl-2-arylamino-4,6-dimethylnicotinonitriles by perchloric acid in a mixture of acetic acid and acetic anhydride. 1-Aryl-2-acetonyl-5,7-dimethyl-4-oxo-1,4-dihydropyrido[2,3-d]pyrimidines areformedonheating2-arylamino-4,6-dimethylnicotinamides with acetic anhydride. These and analogous compounds were obtained by acylation of 1-aryl-2,5,7-trimethyl-4-oxo-1,4-dihydropyrido[2,3-d]pyrimidines with acetic anhydride or benzoyl chloride.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1234–1236, September, 1992.     

Synthesis of novel 1-alkyl or 1-aryl-2-(4-substituted-1-piperazinyl)-1-H-benzothieno[2,3-d]imidazoles

The synthesis of novel 1-alkyl or 1-aryl-2-(4-substituted-1-piperazinyl)-1-H-benzothieno[2,3-d]imidazoles 7e-x starting from 2-nitro-3-bromobenzo[b]thiophene is described. These compounds were prepared as potential H₁-antihistaminic agents.     

Redox thermochemistry of SrFe1-xCoxO3-d

The enthalpy of oxidation of SrFe_1-xCo_xO_3-d with x=0.33 and 0.67 has been determined by adiabatic calorimetry; average values for x=0.33 and 0.67 are -67±11 and -49.5±9 kJ (mol O₂)^-1. These data and the previously reported value for SrFeO_3-d suggest that the enthalpy of oxidation for pure (perovskite-type) SrCoO_3-d is close to zero. Earlier reported composition - partial pressure data for SrFe_0.67Co_0.33O_3-d are reproduced when preferential oxidation of iron is assumed for low partial pressures of oxygen. This revised version was published online in August 2006 with corrections to the Cover Date.