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1.
The preparation of 4-amino-6-hydroxy-1H-pyrrolo[3,2-c]pyridine (3,7-dideazaisoguanine) ( 1 ) in five steps from 1H-pyrrolo[3,2-c]pyridin-4,6(5H,7H) dione (3,7-dideazaxanthine) ( 2 ) is described. Furthermore, prolonged treatment of 1 with 10% aqueous sodium carbonate solution is reported to lead to ring opening of the pyridine of 1 resulting in 3-carboxamidopyrrole-2-acetic acid ( 3 ). 相似文献
2.
The chlorination of 1H-pyrrolo[3,2-c]pyridin-4,6(5H, 7H)dione (3,7-dideazaxanthine) ( 2 ) and 5-methyl-1H-pyrrolo[3,2-c] pyridin4,6(5H,7H)dione (1 -methyl-3,7-dideazaxanthine) ( 3 ) with phenylphosphonic dichloride has yielded 4,6-dichloro-1H-pyrrolo[3,2-c]pyridine (2,6-dichloro-3,7-dideazapurine) ( 1 ). A mechanism for the demethylation of the 5-methyl derivative under these conditions is proposed. Ammonolysis of 4,6-dichloro-1H-pyrrolo[3,2-c] pyridine was unsuccessful while catalytic reduction of this dichloro derivative produced 1H-pyrrolo[3,2-c]-pyridine ( 4 ). 相似文献
3.
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
4.
A facile chemical synthesis of 1H-pyrrolo[3,2-c]pyridin-4,6(5H,7H)dione (3,7-dideazaxanthine) has been accomplished from ethyl 3-ethoxycarbonylpyrrole-2-acetate. 相似文献
5.
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
6.
Some new 7,9-disubstituted 7H-1,2,3,4-tetrazolo[1,5-c]pyrrolo[3,2-e]pyrimidines 5 have been synthesized either by diazotization of 4-hydrazino-5,7-disubstituted-7H-pyrrolo[2,3-d]pyrimidines 4 obtained by hydrazinolysis of 4-chloro-5,7-disubstituted-7H-pyrrolo[2,3-d]pyrimidines 3 or via a substitution reaction between 3 and sodium azide. 5,7-Disubstituted-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-ones 2 were obtained by cyclocondensation of 2-amino-3-cyano-1,4-disubstituted pyrroles 1 with formic acid which on chlorination using phosphorus oxychloride afforded 3 . A novel route for the synthesis of 4-amino-5,7-disubstituted-7H-pyrrolo[2,3-d]pyrimidines 6 by the reductive ring cleavage of 5 has been reported. 相似文献
7.
Nabih S. Girgis Roland K. Robins Howard B. Cottam 《Journal of heterocyclic chemistry》1990,27(2):171-175
Several N-5 ribofuranosyl-2,4-disubstituted pyrrolo[3,2-d]pyrimidine (9-deazapurine) nucleosides were prepared by the single phase sodium salt glycosylation of 2,4-dichloro-5H-pyrrolo[3,2-d]pyrimidine ( 3 ) using 1-chloro-2,3-O-isopropylidene-5-O-(t-butyl)dirnethylsilyl-α-D-ribofuranose ( 2 ). Use of 2 for the glycosylation avoided the formation of “orthoamide” products 1 and provided an excellent yield of the β nucleoside, 2,4-dichloro-5-[2,3-O-isopropylidene-5-O-(t-butyl)dimethylsilyl-β-D-ribofuranosyl]-5H-pyrrolo[3,2-d]pyrimidine ( 4 ), along with a small amount of the corresponding α anomer, 5 . Compound 4 served as the versatile intermediate from which the N-7 ribofuranosyl analogs of the naturally-occurring purine nucleosides adenosine, inosine and guanosine were synthesized. Thus, controlled amination of 4 followed by sugar deprotection and dehalogenation yielded the adenosine analog, 4-amino-5-β-D-ribofuranosyl-5H-pyrrolo[3,2-d]pyrimidine ( 8 ) as the hydrochloride salt. Base hydrolysis of 4 followed by deprotection gave the 2-chloroinosine analog, 10 , and subsequent dehalogenation provided the inosine analog, 5-β-D-ribofuranosyl-5H-pyrrolo[3,2-d]-pyrimidin-4(3H)-one ( 11 ). Amination of 10 furnished the guanosine analog, 2-amino-5-β-D-ribofuranosyl-5H-pyrrolo[3,2-d]pyrimidin-4(3H)-one ( 12 ). Finally, the α anomer in the guanosine series, 16 , was prepared from 5 by the same procedure as that used to prepare 12 . The structural assignments were made on the basis of ultraviolet and proton nmr spectroscopy. In particular, the isopropylidene intermediates 9 and 14 were used to assign the proper configuration as β and α, respectively, according to Imbach's rule. 相似文献
8.
Nabih S. Girgis Steven B. Larson Roland K. Robins Howard B. Cottam 《Journal of heterocyclic chemistry》1989,26(2):317-325
Certain 4-substituted 1H-pyrrolo[2,3-b]pyridines (7-azaindoles) undergo a nucleophilic substitution-rearrangement upon treatment with various primary amines at elevated temperatures to yield N-1-substituted 4-amino-1H-pyrrolo[3,2-c]pyridines (5-azaindoles). Treatment of the same 7-azaindoles with secondary amines under the same reaction conditions led to simple nucleophilic substitution products. 相似文献
9.
I. V. Rudenko A. A. Kucherak A. A. Tolmachev O. V. Hordiyenko 《Chemistry of Heterocyclic Compounds》2011,47(8):964-969
An efficient method has been developed for the synthesis of 4,6-dimethylpyridine-2,3-dicarbonitrile. A study was carried out
on the reaction of this compound with N-acylhydrazines to give two structural isomers, namely, N′-(7-amino-2,4-dimethyl-5H-pyrrolo[3,4-b]pyridin-5-ylidene)carbohydrazides and N′-(5-amino-2,4-dimethyl-7H-pyrrolo[3,4-b]pyridin-7-ylidene)carbohydrazides as well as disubstituted N′,N″-(2,4-dimethyl-5H-pyrrolo[3,4-b]pyridine-5,7-diylidene)dicarbohydrazides. 相似文献
10.
R. Madhav Carroll A. Snyder Philip L. Southwick 《Journal of heterocyclic chemistry》1980,17(6):1231-1235
1-(ω-Carboxyalkyl)-4-carboethoxy-2,3-dioxopyrrolidines were prepared by a one-pot synthesis from β-alanine or γ-aminobutyric acid, ethyl acrylate and diethyl oxalate. In a second one-pot process these products were hydrolyzed, decarboxylated and condensed with aromatic aldehydes under the influence of hydrochloric acid to yield 1-(ω-carboxyalkyl)-4-arylidene-2,3-dioxo-pyrolidines, which yielded 2-amino-4-aryl-6-(ω-carboxyalkyl)-5H-pyrrolo[3,4-d]pyrimidin-7-(6H)-ones upon treatment with guanidine. It was shown that 3,4-dihydro derivatives of certain 2-amino-4-aryl-5H-pyrrolo[3,4-d]pyrimidin-7-(6H)ones, formed initially in the guanidine reaction, readily undergo conversion to 5H-pyrrolo[3,4-d]pyrimidin-7-(6H)ones. 相似文献
11.
Philip E. Morris Arthur J. Elliott John A. Montgomery 《Journal of heterocyclic chemistry》1999,36(2):423-427
In a recent publication, we have the described the synthesis of 7-substituted-2-amino-1,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-ones which are potent inhibitors of the enzyme Purine Nucleoside Phosphorylase from the corresponding 3-aminopyrroIe-2-carboxylate esters. A key step in the synthesis is condensation of the amino group with the highly reactive guanylating reagents 3 or 4 followed by annulation. The furo[3,2-d]pyrimidin-4-one and thieno[3,2-d]pyridin-4-one are closely related rings systems. However, these rings have not been reported in the literature with a 2-amino, substituent which would arise from such guanylation reactions. In this report, the syntheses of the novel furans 5 are described based on our improved pyrrole synthesis (Scheme 1). The syntheses of the novel thiophenes 6 are described. The guanylation of 5 and 6 were studied and compared to 2. The 3-amino group of 5 and 6 failed to react with 3 or 4 under mild acid catalysis; conditions under which 2 easily condensed. Guanylation was finally achieved by generating the carbodiimide intermediate of 3 under mercury catalysis affording the guanylated adducts which were converted to the novel 2-aminothieno- and furo[3,2-d]pyrimidin-4-ones 16. 相似文献
12.
Huaqian Chen Tao Lu Minglong Qiao Jiawen Hu Chunmei Li Chenze Qi Furen Zhang 《Journal of heterocyclic chemistry》2021,58(11):2132-2139
A series of 1,5-dihydro-4H-pyrrolo[3,2-c]pyridin-4-one derivatives with 3-(4-hydroxy-2-oxo-2H-pyran-3-yl) groups were synthesized via a one-pot three-component reaction of 4-aminopyridin-2(1H)-ones, 2,2-dihydroxy-1-arylethan-1-ones, and 4-hydroxy-2H-pyran-2-ones in water. This strategy not only provides a valuable tool in the design and synthesis of new hydrogenated pyrrolo[3,2-c]pyridines but also has the advantages of inexpensive starting materials, atom and step economy, environmental friendliness, good to excellent yields, and operational simplicity. A total of 14 examples were examined to show a broad substrate scope and high yields. 相似文献
13.
Hitoxhi Fujimori Yasutaka Kayama Takeshi Hara Kazuhiko Itoh Tamiko Sunami 《Journal of heterocyclic chemistry》1977,14(2):235-240
The synthesis of 4H-pyrrolo[1,2-a]thieno[3,2-f] [1,4]diazepines ( 8 ) is described. Phthal-imidomethylfurans 1 were treated with bromine-methanol to give the dihydrofurans 2 , which were hydrolyzed and then liydrogenated over Raney nickel or with zinc-acetic acid to afford the 1,4-diketones 5 . Condensation of 2-amino-3-benzoylthiophenes 6 with 5 gave 3-benzoyl-2-pyrrolylthiopenes 7 . The removal of the phthaloyl group from 7 with hydrazine hydrate and ring closure to the diazepine ring yielded the new heterocycles 8 . 相似文献
14.
Substituted 2-amino-4-aryl-3-cyano-5-oxo-5,6-dihydro-4H-pyrano[2,3-d]pyrido[3",2":4,5]thieno[3,2-b]pyridines were synthesized by the reactions of 4-hydroxy-1H-thieno[2,3-b;4,5-b]dipyridin-2-ones with arylidenemalononitriles or by the three-component reactions of hydroxythienodipyridinones with aldehydes and malononitrile in DMF in the presence of triethylamine. Methods for syntheses of substituted 3-alkoxycarbonyl-6-amino-4-aryl-2-(3-cyanopyridin-2-ylthiomethyl)-4H-pyrans were developed on the basis of the reactions of 4-(3-cyanopyridin-2-ylthio)acetoacetates and arylidenemalononitriles or aldehydes and malononitrile. Ethyl 4-(3-cyanopyridin-2-ylthio)acetoacetate and 4-methoxybenzylidenecyanothioacetamide were used for the synthesis of 6-(pyridin-2-ylthiomethyl)-3-cyanopyridine-2(1H)-thione. 相似文献
15.
Tadasu Tanaka Takeo Iwakuma Mitsuyoshi Wagatsuma Ikuo Iijima 《Journal of heterocyclic chemistry》1972,9(6):1355-1358
This paper describes the syntheses and the properties of 1H-pyrrolo[2,3-6]quinolines derived from 2,3-dihydrofuro[3,2-c]quinolines or 3-(β-chloroethyl)-2,4-dichloroquinolines. The discrepancy on the physical data of 1H-pyrrolo[2,3-b]quinoline between our product and Perkin's previously reported product is also discussed. 相似文献
16.
4-Methylfuro[3′,2′:5,6]benzofuro[3,2-c]pyridine ( 3 ) was synthetized from 2-acetylfuro[3,2-f]benzo[b]furan ( 4 ) or from 2-acetyl-5,6-dihydrofuro[3,2-f]benzo[b]furan ( 10 ). The key step involves a rearrangement-cyclization of azides 6 and 12 to form 4-methylfuro[3′,2′:5,6]benzofuro[3,2-c]pyridin-1(2H) one ( 7 ) and 8,9-dihydro-4-methylfuro[3′,2′:5,6]benzofuro[3,2c]pyridin-1(2H)-one ( 13 ). Introduction of an aminoalkyl chain on carbon 1 was effected by substitution of 1-chloro-4-methylfuro[3′,2′:5,6]benzofuro[3,2-c]pyridine ( 8 ). 相似文献
17.
Piergiorgio Pecorari Marcella Rinaldi Maria Paola Costi Luciano Antolini 《Journal of heterocyclic chemistry》1991,28(4):891-898
The cyclization reactions, carried out in strongly- or weakly-basic media, are described. Sometimes, 7-amino-2,3-dihydro-3-hydroxymethyl-5H-thiazolo[3,2-a]pyrimidin-5-one is separated out, together with 8-amino-3,4-dihydro-3-hydroxy-2H,6H-pyrimido[2,1-b][1,3]thiazin-6-one, as the principal product. A mechanism of reaction, during which the cyclizating agents are changed into oxirane derivatives, is proposed. The results of single-crystal X-ray investigations on 8-amino-3,4-dihydro-3-hydroxy-7-nitroso-2H,6H-pyrimido[2,1-b][1,3]thiazin-6-one (R = 0.035 for 1013 reflections), and on 7-hydroxymethyl-6,7-dihydrothiazolo[3,2-a][1,2,3]triazolo[4,5-d]pyrimidin-9(1H)-one (R = 0.027 for 1607 reflections) are reported. 相似文献
18.
Synthesis of 2-amino-6-hydroxymethyl-4-(3H)pyrido[3,2-d]pyrimidinone ( 5 ) from 2-amino-6-methyl-4-(3H)-pyrido[3,2-d]pyrimidinone ( 2 ) was accomplished by selenium dioxide oxidation of 2 to the aldehyde 4 followed by sodium borohydride reduction. Compound 2 was available in four steps from 5-aminouracil or in two steps from 5-nitroisocytosine ( 3a ). Catalytic reduction of 4 or 5 gave a mixture of 2-amino-6-methyl-5,6,7,8-tetrahydro-4-(3H)pyrido[3,2-d]pyrimidinone ( 6a ) and the 6-hydroxymethyl compound 6b . These compounds showed only weak inhibitory activity in the coupled reactions catalyzed by 7,8-dihydro-6-hydroxymethylpterin pyrophosphokinase and 7,8-dihydropteroate synthetase from E. Coli. No significant antibacterial activity was observed. 相似文献
19.
Avetisyan A. A. Aleksanyan I. L. Ambartsumyan L. P. 《Russian Journal of Organic Chemistry》2010,46(3):427-431
6(8)-Substituted 4-hydrazino-2-methylquinolines were synthesized by reaction of the corresponding 4-chloro-2-methylquinolines
with hydrazine hydrate. Reactions of the title compounds with ethyl acetoacetate and acetone gave 2,4-dimethyl-1H-pyrrolo[3,2-c]quinolines and 4-(5-ethoxy-3-methyl-1H-pyrazol-1-yl)-2-methylquinolines. 相似文献
20.
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