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1.
4-Benzylamino-6-methyl-1H-pyrrolo[3,2-c]pyridine ( 2 ) and 4-benzylamino-6-methyl-1H-pyrrolo[2,3-b]pyridine ( 3 ) were synthesized as deaza analogues of the anxiolytic agent 4-benzylamino-2-methyl-7H-pyrrolo[2,3-d]pyrimidine ( 1 ). The 1-deaza analogue (2) was prepared via a multi-step procedure from a pyrrole precursor, 1-benzyl-2-formylpyrrole ( 4 ) while the 3-deaza analogue 3 was synthesized from a pyridine precursor, 2-amino-3,6-dimethylpyridine ( 12 ). 相似文献
2.
Guanidine transforms the following: (a) 3-formylchromone into a mixture of 2-amino-5-(2-hydroxybenzoyl)pyrimidine and 2-amino-5H-[1]-benzopyrano[4,3-d]pyrimidine; (b) the diacetate of 3-methylidyne-chromone into 2-amino-5-hydroxy-5H-[1]benzopyrano[4,3-d]pyrimidine; and (c) the oxime of 3-formylchromone into 2-amino-5H-[1]benzopyrano-[4,3-d]pyrimidin-5-one. Thiourea, acetamidine and nitroguanidine can also generate pyrimidines of the same type with 3-formylchromone, the diacetate of 3-methylidynechromone or 3-(1,3-dioxolan)chromone. 相似文献
3.
Nabih S. Girgis Howard B. Cottam Steven B. Larson Roland K. Robins 《Journal of heterocyclic chemistry》1987,24(3):821-827
A number of 2,4-disubstituted pyrrolo[3,2-d]pyrimidine N-5 nucleosides were prepared by the direct glycosylation of the sodium salt of 2,4-dichloro-5H-pyrrolo[3,2-d]pyrimidine (3) using 1-chloro-2-deoxy-3,5-di-O-(p-toluoyl)-α-D -erythropentofuranose (1) and 1-chloro-2,3,5-tri-O-benzyl-α-D-arabinofuranose (11) . The resulting N-5 glycosides, 2,4-dichloro-5-(2-deoxy-3,5-di-O-(p-toluoyl) -β-D-erythropentofuranosyl)-5H-pyrrolo-[3,2-d]pyrimidine (4) and 2,4-dichloro-5-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl-5H -pyrrolo [3,2-d)pyrimidine (12) , served as versatile key intermediates from which the N-7 glycosyl analogs of the naturally occurring purine nucleosides adenosine, inosine and guanosine were synthesized. Thus, treatment of 4 with methanolic ammonia followed by dehalogenation provided the adenosine analog, 4-amino-5-(2-deoxyerythropentofuranosyl) -5H-pyrrolo[3,2-d]pyrimidine (6) . Reaction of 4 with sodium hydroxide followed by dehalogenation afforded the inosine analog, 5-(2-deoxy-β-D-erythropentofuranosyl) -5H-pyrrolo[3,2-d]pyrimidin-4(3H)-one (9) . Treatment of 4 with sodium hydroxide followed by methanolic ammonia gave the guanosine analog, 2-amino-5-(2-deoxy-β-D-erythropentofuranosyl) -5H-pyrrolo[3,2-d]pyrimidin-4(3H)-one (10) . The preparation of the same analogs in the β-D-arabinonucleoside series was achieved by the same general procedures as those employed for the corresponding 2′-deoxy-β-D-ribonucleoside analogs except that, in all but one case, debenzylation of the sugar protecting groups was accomplished with cyclohexene-palladium hydroxide on carbon, providing 4-amino-5-β-D-arabinofuranosyl-5H-pyrrolo [3,2-d]pyrimidin-4(3H)-one (18) . Structural characterization of the 2′-deoxyribonucleoside analogs was based on uv and proton nmr while that of the arabinonucleosides was confirmed by single-crystal X-ray analysis of 15a . The stereospecific attachment of the 2-deoxy-β-D-ribofuranosyl and β-D-arabinofuranosyl moieties appears to be due to a Walden inversion at the C1 carbon by the anionic heterocyclic nitrogen (SN2 mechanism). 相似文献
4.
H. H. Abdel-Razik 《Chemical Papers》2006,60(4):268-273
2H-5-Amino-6-cyano-3,7-dioxothiazolo[2,3-b]pyrimidine was subjected to ring formation affording thiazolo[2,3-b]pyrimidine derivatives. 2H-5-Amino-6-cyano-3,7-dioxo-2-phenylmethylenethiazolo[2,3-b]pyrimidine was also subjected to ring formation affording pyrimido[4,5-d]-, pyrano[2,3-d]-, and pyrido[2,3-d]thiazolo[2,3-b]pyrimidine derivatives. 2-Anilinothiocarbonyl-3,9-dioxo-8-imino-7-phenyl-6-thioxothiazolo[2,3-b]pyrimido[4,5-d]pyrimidine and 8-amino-3,9-dioxo-6-thioxothiazolo[2,3-b]pyrimido[4,5-d]pyrimidine reacted with α-haloactive-methylene compounds to afford heterocyclic compounds containing two, fused and isolated, thiazole moieties, respectively. 相似文献
5.
T. Sudhakar Rao Ganapathi R. Revankar Ravi S. Vinayak Roland K. Robins 《Journal of heterocyclic chemistry》1991,28(7):1779-1788
Several disubstituted pyrazolo[3,4-d]pyrimidine, pyrazolo[1,5-a]pyrimidine and thiazolo[4,5-d]pyrimidine ribonucleosides have been prepared as congeners of uridine and cytidine. Glycosylation of the trimethylsilyl (TMS) derivative of pyrazolo[3,4-d]pyrimidine-4,6(1H,5H,7H)-dione ( 4 ) with 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose ( 5 ) in the presence of TMS triflate afforded 7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)pyrazolo-[3,4-d]pyrimidine-4,6(1H,5H)-dione ( 6 ). Debenzoylation of 6 gave the uridine analog 7-β-D-ribofuranosylpyrazolo[3,4-d]pyrimidine-4,6(1H,5H)-dione ( 3 ), identical with 7-ribofuranosyloxoallopurinol reported earlier. Thiation of 6 gave 7 , which on debenzoylation afforded 7-β-D-ribofuranosyl-6-oxopyrazolo[3,4-d]pyrimidine-4(1H,5H)-thione ( 8 ). Ammonolysis of 7 at elevated temperature gave a low yield of the cytidine analog 4-amino-7-β-D-ribofuranosylpyrazolo[3,4-d]pyrimidin-6(1H)-one ( 11 ). Chlorination of 6 , followed by ammonolysis, furnished an alternate route to 11 . A similar glycosylation of TMS-4 with 2,3,5-tri-O-benzyl-α-D-arabinofuranosyl chloride ( 12 ) gave mainly the N7-glycosylated product 13 , which on debenzylation provided 7-β-D-arabinofuranosylpyrazolo[3,4-d]pyrimidine-4,6(1H,5H)-dione ( 14 ). 4-Amino-7-β-D-arabinofuranosyl-pyrazolo[3,4-d]pyrimidin-6(1H)-one ( 19 ) was prepared from 13 via the C4-pyridinium chloride intermediate 17 . Condensation of the TMS derivatives of 7-hydroxy- ( 20 ) or 7-aminopyrazolo[1,5-a]pyrimidin-5(4H)-one ( 23 ) with 5 in the presence of TMS triflate gave the corresponding blocked nucleosides 21 and 24 , respectively, which on deprotection afforded 7-hydroxy- 22 and 7-amino-4-β-D-ribofuranosylpyrazolo[1,5-a]pyrimidin-5-one ( 25 ), respectively. Similarly, starting either from 2-chloro ( 26 ) or 2-aminothiazolo[4,5-d]pyrimidine-5,7-(4H,6H)-dione ( 29 ), 2-amino-4-β-D-ribofuranosylthiazolo[4,5-d]pyrimidine-5,7(6H)-dione ( 28 ) has been prepared. The structure of 25 was confirmed by single crystal X-ray diffraction studies. 相似文献
6.
The reaction of 6-amino-1,3-dimethyluracil with equimolar amounts of arylalkanone Mannich bases under optimized reaction conditions leads to 7-aryl-5,6-dihydropyrido[2,3-d]pyrimidines in a yield of 50-80%. Functionalization of these dihydropyridopyrimidine(1H,3H)-2,4-diones with the Vilsmeier reagent affords, depending on the reaction conditions, either 6-dimethylaminomethylidene substituted 5H-pyrido[2,3-d]pyrimidine(1H,3H)-2,4-diones or the corresponding pyridopyrimidine(1H,3H)-2,4-diones bearing a carboxaldehyde function in position 6 of the heterocycle. Some further transformations of the aldehyde function demonstrate the synthetic potential of the synthesized structures, introducing pharmacologically relevant basic substituents into the side chain of these pyrido[2,3-d]pyrimidine derivatives. 相似文献
7.
V. B. Sokolov A. Yu. Aksinenko T. A. Epishina T. V. Goreva 《Russian Journal of General Chemistry》2014,84(7):1358-1361
A new method of the synthesis of heterocyclic derivatives of trifluoroalanine based on the cyclocondensation of methyl trifluoropyruvate tert-butoxycarbonylimine with C,N- and N,N-binucleophiles, like Nsubstituted ureas, 1-benzyl-6-aminouracil, benzamidine, and 3-aminocrotononitrile, followed by hydrolysis of the resulting Boc-derivatives to 5-amino-5-trifluoromethylimidazolidine-2,4-diones, 5-amino-5-trifluoromethyl-1-benzyl-5,7-dihydropyrrolo[2,3-d]-pyrimidine-2,4,6-3H-trione, 4-amino-2-methyl-5-oxo-4-(trifluoromethyl)-4,5-dihydro-1H-pyrrole-3-carbonitrile, or 5-amino-5-trifluoromethyl-2-phenyl-3,5-dihydroimidazol-4-one, respectively, was developed. 相似文献
8.
Jack D. Anderson N. Kent Dalley Ganapathi R. Revankar Roland K. Robins 《Journal of heterocyclic chemistry》1986,23(6):1869-1878
Several 3-alkoxysubstituted pyrazolo[3,4-d]pyrimidine ribonucleosides structurally related to adenosine, inosine and guanosine have been prepared by the direct glycosylation of preformed aglycon precursor containing a 3-alkoxy substituent. Ring closure of 5(3)-amino-3(5)-ethoxypyrazole-4-carboxamide ( 6b ) with either formamide or potassium ethyl xanthate gave 3-ethoxyallopurinol ( 7b ) and 3-ethoxy-6-thioxopyrazolo[3,4-d]-pyrimidin-4(5H,7H)-one ( 10 ), respectively. Methylation of 10 gave the corresponding 6-methylthio derivative 15 . Similar ring annulation of 5(3)-methoxypyrazole-4-carboxamide ( 6a ) with formamide afforded 3-methoxyallopurinol ( 7a ). Treatment of 5(3)-amino-3(5)-methoxypyrazole-4-carbonitrile ( 5a ) with formamidine acetate furnished 4-amino-3-methoxypyrazolo[3,4-d]pyrimidine ( 4 ). High-temperature glycosylation of 7b with 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose in the presence of boron trifluoride etherate gave a 2:1 mixture of N-1 and N-2 glycosyl blocked nucleosides 11b and 13b . Deprotection of 11b and 13b with sodium methoxide gave 3-ethoxy-1-β-D-ribofuranosylpyrazolo[3,4-d]pyrimidin-4(5H)-one ( 12b ) and the corresponding N-2 glycosyl isomer 14b , respectively. Similar glycosylation of either 4 or 7a , and subsequent debenzoylation gave exclusively 4-amino-3-methoxy-1-β-D-ribofuranosylpyrazolo[3,4-d]pyrimidine ( 9 ) and 3-methoxy-1-β-D-ribofuranosylpyrazolo[3,4-d]pyrimidin-4-(5H)-one ( 12a ), respectively. The structural assignment of 12a was made on the basis of single-crystal X-ray analysis. Application of this general glycosylation procedure to 15 gave the corresponding N-1 glycosyl derivative 16 as the sole product, which on debenzoylation afforded 3-ethoxy-6-(methylthio)-1-(3-D-ribofuranosylpyrazolo[3,4-d]pyrimidin-4(5H)-one ( 17 ). Oxidation of 16 and subsequent ammonolysis furnished the guanosine analog 6-arnino-3-ethoxy-1-β-D-ribofuranosylpyrazolo[3,4-d]-pyrimidin-4(5H)-one ( 19 ). Similarly, starting from 3-methoxy-4,6-bis(methylthio)pyrazolo[3,4-d]pyrimidine ( 20 ), 6-amino-3-methoxy-1-β-D-ribofuranosylpyrazolo[3,4-d]pyrimidin-4(5H)-one ( 23 ) was prepared. 相似文献
9.
M. T. Wu M. MacCoss T. J. Ikeler J. Hirshfield B. H. Arison R. L. Tolman 《Journal of heterocyclic chemistry》1990,27(6):1559-1563
Tricyclic analogs of piperazinylthiopyrano[3,2-d]pyrimidine hypoglycemic agents were prepared. The angular tricyclic systems, 8,9-dihydro-7H-thiopyrano[2,3-e][1,2,4]triazolo[4,3-a]pyrimidine and 8,9-dihydro-7H-tetrazolo[1,5-a]thiopyrano[2,3-e]pyrimidine derivatives were synthesized from 2,4-dichloro-7,8-dihydro-6H-thiopyrano[3,2-d]pyrimidine in three step sequences. Derivatives of the linear tricyclic system, 5,6-dihydro-7H-thiopyrano[3,2-d][1,2,4]triazolo[2,3-a]pyrimidine, were prepared by condensation of 3-amino-1,2,4-triazole with ethyl 3-oxo-tetrahydropyran-2-carboxylate. The tricyclic heteroaryl-piperazines lacked significant hypoglycemic activity. 相似文献
10.
Leila Moafi 《Tetrahedron letters》2010,51(48):6270-6274
The synthesis of 2-amino-4-cyano-4H-chromene derivatives as new HA 14-1 analogues by a simple and efficient method is reported. In addition, the reaction of 2-amino-2H-chromene-3-carbonitriles, salicylaldehydes and amines results in the formation of new chromeno[2,3-d]pyrimidine derivatives. 相似文献
11.
Starting from 7-chloro-3-methyl-1H-pyrazolo[4,3-d]pyrimidine ( 1 ) by reaction with methanol/hydrogen chloride, subsequent methylation and reaction with N-bromosuccinimide 3-bromomethyl-7-methoxy-1-methyl-1H-pyrazolo[4,3-d]pyrimidine ( 6 ) is prepared. Treatment with ethylene glycol in the presence of potassium carbonate/potassium iodide and subsequent reaction with ethanolic ammonia afforded 7-amino-3-(2-hydroxyethoxymethyl)-1-methyl-1H-pyrazolo[4,3-d]pyrimidine ( 11 ) an acyclo analog of formycin A. 相似文献
12.
The reaction between 5-amino-4-imino-1(2)-substituted-1(2)H-4,5-dihydropyrazolo[3,4-d]pyrimidines and several commercially available reactants afforded new heterocycles with a conserved pyrazolo[3,4-d]pyrimidine nucleus. The key intermediates employed proved to be suitable compounds by virtue of their two vicinal amino and imino groups that were used to obtain five, six and seven-membered rings. 相似文献
13.
Nasser M. El-Gohary Azza M. El-Kazak Magdy A. Ibrahim 《Journal of heterocyclic chemistry》2020,57(2):716-723
Polyfunctional 3-chloro-3-(4-chlorocoumarin-3-yl)prop-2-enal ( 1 ) used as a precursor for heterocyclic synthesis. Dichloro-aldehyde 1 was allowed to react with variable nucleophilic reagents, and a diversity of heterocyclic systems linked coumarin moiety at position 3 was synthesized. The reaction of compound 1 with guanidine and cyanoguanidine produced 3-(pyrimidin-4-yl)-4-chlorocoumarins 2 and 3 . Treating compound 1 with 3-amino-1,2,4-triazole and 2-aminobenzimidazole yielded triazolo[4,3-a]pyrimidine 4 and pyrimido[1,2-a]benzimidazole 5 . The treatment of compound 1 with cyanoacetamide, N-benzyl-2-cyanoacetamide, and 1H-benzimidazolylacetonitrile gave 2(1H)-pyridones 6 , 7 and pyrido[1,2-a]benzimidazole 8 . The reaction of compound 1 with 5-amino-3-methyl-1H-pyrazole and 6-aminouracil afforded pyrazolo[3,4-b]pyridine 9 and pyrido[2,3-d]pyrimidine 10 , respectively. Compound 1 reacted with ethylenediamine, o-phenylenediamine , o-aminophenol, and o-aminothiophenol leading to 5-(imidazolylmethyl)chromeno[4,3-e] [1,4]diazepine ( 12 ), 3-(benzodiazepin/benzoxazepin-2-yl)-4-chlorocoumarins 13 , 14 , and 6-(benzothiazol-2-ylmethyl)chromeno[4,3-b][1,5]benzothiazepine 16 , respectively. Structures of the new synthesized products were deduced on the basis of their analytical and spectral data. 相似文献
14.
Jack D. Anderson Howard B. Cottam Steven B. Larson L. Dee Nord Ganapathi R. Revankar Roland K. Robins 《Journal of heterocyclic chemistry》1990,27(2):439-453
Synthesis of the pyrazolo[3,4-d]pyrimidin-3-one congeners of guanosine, adenosine and inosine is described. Glycosylation of 3-methoxy-6-methylthio-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one ( 13 ) with 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose ( 16 ) in the presence of boron trifluoride etherate gave 3-methoxy-6-methylthio-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)pyrazolo[3,4-d]pyrimidin-4(5H)-one ( 17 ) which, after successive treatments with 3-chloroperoxybenzoic acid and methanolic ammonia, afforded 6-amino-3-methoxy-1-β-D-ribofuranosylpyrazolo[3,4-d]pyrimidin-4(5H)one ( 18 ). The guanosine analog, 6-amino-1-β-D-ribofuranosylpyrazolo[3,4-d]pyrimidine-3,4(2H,5H)-dione ( 21 ), was made by sodium iodide-chlorotrimethylsilane treatment of 6-amino-3-methoxy-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)pyrazolo[3,4-d]pyrimidin-4(5H)one ( 19 ), followed by sugar deprotection. Treatment of the adenine analog, 4-amino-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one ( 11 ), according to the high temperature glycosylation procedure yielded a mixture of N-1 and N-2 ribosyl-attached isomers. Deprotection of the individual isomers afforded 4-amino-3-hydroxy-1-βribofuranosylpyrazolo-[3,4-d]pyrimidine ( 26 ) and 4-amino-2-β-D-ribofuranosylpyrazolo[3,4-d]pyrimidin-3(7H)-one ( 27 ). The structures of 26 and 27 were established by single crystal X-ray diffraction analysis. The inosine analog, 1-β-D-ribofuranosylpyrazolo[3,4-d]pyrimidine-3,4(2H,5H)-dione ( 28 ), was synthesized enzymatically by direct ribosylation of 1H-pyrazolo[3,4-d]pyrimidine-3,4(2H,5H)-dione ( 8 ) with ribose-1-phosphate in the presence of purine nucleoside phosphorylase, and also by deamination of 26 with adenosine deaminase. 相似文献
15.
The reaction of 4-chloro-5-cyano-2-methylthiopyrimidine (I) with ethyl mercaptosuccinate (II) in refluxing ethanol containing sodium carbonate has afforded diethyl 3-amino-2-(methyl-thio)-7H-thiopyrano[2,3-d]pyrimidine-6,7-dicarboxylate (IV). Displacement of the methylthio group in IV with hydrazine gave the corresponding hydrazino derivative which underwent Schiff base formation with benzaldehyde or 2,6-dichlorobenzaldehyde. Treatment of IV in refluxing acetic anhydride afforded the corresponding diacetylated amino derivative. Partial saponification of IV with sodium hydroxide gave 5-amino-2-(methylthio)-7H-thiopyrano-[2,3-d]pyrimidine 6,7-dicarboxylic acid 6 ethyl ester (VIII). The reaction of 4-amino-6-chloro-5-cyano-2-phenylpyrirnidine (XI) with II resulted in the formation of ethyl 4-amino-6-(ethoxy-carbonyl)-5,6-dihydro-5-amino-2-phenylthieno[2,3-d]pyrimidine-6-acetate (XIII) which when subjected to hydrolysis gave ethyl 4,5-diamino-2-phenylthieno[2,3-d]pyrimidine-6-acetate isolated as the hydrochloride (XIV). Diazotization of IV with sodium nitrite in acetic acid unexpectedly afforded diethyl 5-(acetyloxy)-6,7-dihydro-6-hydroxy-2-(methylthio)-5H-thio-pyrano[2,3-d]pyrimidine-6,7-diearboxylate (XV). Several structural ambiguities were resolved by ir and pmr spectra. 相似文献
16.
Wan-Chen Pan Yi-Chun Wang Tuan-Jie Li Jian-Quan Liu Xiang-Shan Wang 《Journal of heterocyclic chemistry》2020,57(11):3970-3979
Aldehyde could undergo not only the subsequent condensation and cyclization with 2-aminothiophene-3-carboxamide to build a pyrimidine ring, but also a Friedel-Crafts alkylation reaction with thiophene moiety to give unexpected 6-benzyl-2-arylthieno[2,3-d]pyrimidin-4(3H)- ones in good yields catalyzed by concentrated HCl. 相似文献
17.
3H-benzothieno[3,2-d]pyrimidin-4-one (3) was synthesized by bimolecular cyclising the 3-amino-2-carbethoxybenzothiophene (1) with formamide. The electrophilic substituion of 3 afforded N-methylated lactam derivavtives, the structure of which was assigned by 'H nmr and unequivocal synthesis. The sysnthesis of benzothieno[3,2-d]pyrimidine (7) was achieved by desulphurization of the 3H-benzothieno[3,2-d]-[3,2-d]pyrimisine-4-thione (6) or by oxydation of the 4-hydrazinobenzothieno[3,2-d]primidine (5). 相似文献
18.
A multistep synthesis of ethyl 5-amino-2-methyIpyridine-4-carboxylate (5a) starting from ethyl acetopyruvate and nitroacetamide is described. The condensation of 5a with benzoylcyanamide gave 2-amino-3-benzoyl-6-methylpyrido[3,4-d]pyrimidin-4(3H) one (10), which could be hydrolyzed in alkali to give 2-amino-4-hydroxy-6-methylpyrido[3,4-d]pyrimidine (9). Free radical bromination of 10 in bromotrichloromethane gave a mixture of the bromo- and chloromethyl- derivatives (11). Fusion of 11 with ethyl p-aminobenzoate, followed by alkaline hydrolysis gave the corresponding pteroic acid analog (12). 相似文献
19.
Libraries of skeletally diverse potential bioactive polycyclic/spirocyclic heterocyclic compounds; 2-amino-7,9-dimethyl-5-oxo-4-aryl-4,5,6,7-tetrahydropyrano[2,3-d]pyrazolo[3,4-b]pyridine-3-carbonitrile, 2′-amino-7′,9′-dimethyl-2,5′-dioxo-6′,7′-dihydro-5′H-spiro[indoline-3,4′-pyrano[2,3-d]pyrazolo[3,4-b]pyridine]-3′-carbonitrile, and 5,5′-(arylmethylene)bis(4-hydroxy-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one) have been synthesized through a multi-component reaction using novel heterocyclic active methylene compound 4-hydroxy-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-6(7H)-one as one of the building blocks. This protocol can be considered to be an efficient and eco-friendly strategy for diversity oriented synthesis. 相似文献
20.
The reaction of N-arylcyanamides with thiophene o-aminonitriles under the influence of dry hydrogen chloride gas yields a mixture of two products. The major product has been identified as 2-amino-3-aryl-4-iminothieno[2,3-d]pyrimidine and the minor as 2-amino-3-arylthieno[2,3-H]pyrimidin-4(3H)-one. 相似文献