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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.
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
3.
Stewart W. Schneller Jiann-Kuan Luo Ramachandra S. Hosmane Rainer H. DÚrrfeld 《Journal of heterocyclic chemistry》1984,21(4):1153-1155
The synthesis of 1-methyl- ( 1a ) and 1-benzyl-6-amino-1H-pyrrolo[3,2-c]pyridin-4(5H)-one ( 1b ) from the appropriate N-alkylaminoacetaldehyde is described. These provide examples of a synthetic procedure that can be used to prepare 1-substituted 6-amino-1H-pyrrolo[3,2-c]pyridin-4(5H)-ones wherein the N-1 substituent is regiospecifically placed. 相似文献
4.
Dyachenko V. D. Dyachenko A. D. Chernega A. N. 《Russian Journal of Organic Chemistry》2004,40(3):397-406
Cyclopentylidene- and cyclohexylidene(cyano)acetamides reacted with malononitrile and cyano-(thioacetamide) according to the Michael pattern with exchange of the methylene components to give substituted 1-amino-2,6,6-tricyano-1,3-cyclohexadienes and thieno[2,3-d]pyrimidine-4(3H)-thiones. Condensation of cyclopentylidene- and cyclohexylidene(cyano)acetamide with 1,3-dicarbonyl compounds afforded 4,6-di-methyl-3-cyanopyridine-2(1H)-thione and morpholinium 4-methyl-6-oxo-3-cyano-1,6-dihydropyridine-2-thiolate which were converted into substituted 2-alkylsulfanylpyridines, thieno[2,3-b]pyridines, thiazolo[3,2-a]pyridine, and 2H-[1,3]thiazino[3,2-a]pyridine. 相似文献
5.
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
6.
5,7-Diamino[1,3,4]thiadiazolo[3,2-a]pyrirnidinium chloride 2 , 7-amino[1,2,4]triazolo[1,5-c]pyrimidine-5(6H)-thiones 3 and the 5(6H)-one derivative 4a were synthesized by the reaction of 1,4,6-triaminopyrimidine-2(1H)-thione 1 with phosphoryl chloride and N,N-dimethylacylamides. Further, compounds 4 were prepared from 2, 3 or 1,4,6-triaminopyrimidin-2(1H)-one 6 by the treatment with the above reagents. Compounds 3 and 4 were converted to 7-amino[1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-ones 5 . 相似文献
7.
The synthesis of pyrrolo[3,4-c] [1] benzazepine-4,10(2H, 5H)-dione, a compound related to 11-oxosibiromycinone, is described. 2-Methyl-, 5-methyl- and 2,5-dimethylpyrrolo[3,4-c] [1] benzazepine-4, 10 (2H, 5H) - dione have been also prepared. The title compound has been synthesized either by ring enlargement of 2H-benz [f] isoindole-4,9-dione or by TosMIC addition to 1H-1-benzazepin-2,5-dione. 相似文献
8.
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
9.
Nabih S. Girgis Roland K. Robins Howard B. Cottam 《Journal of heterocyclic chemistry》1990,27(7):1989-1991
Nucleosides of pyrrolo[2,3-d]pyridazin-4(5H)-ones were prepared by the single-phase sodium salt glycosylation of appropriately functionalized pyrrole precursors. The glycosylation of the sodium salt of ethyl 4,5-dichloro-2-formyl-1H-pyrrole-3-carboxylate ( 4 ), or its azomethino derivative 7 , with 1-bromo-2,3,5-tri-O-benzoyl-D-ribofuranose in acetonitrile afforded the corresponding substituted pyrrole nucleosides ethyl 4,5-dichloro-2-formyl-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1H-pyrrole-3-carboxylate ( 5 ) and ethyl 4,5-dichloro-2-phenylazomethino-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1H-pyrrole-3-carboxylate ( 8 ), respectively. The latter, upon treatment with hydrazine, afforded the annulated product 2,3-dichloro-1-β-D-ribofuranosyl-1H-pyrrolo[2,3-d]pyridazin-4(5H)-one ( 6 ), in good yield. The unsubstituted analog 1-β-D-ribofuranosyl-1H-pyrrolo[2,3-d]pyridazin-4(5H)-one ( 9 ), was obtained upon catalytic dehalogenation of 6 . This report represents the first example of the synthesis of nucleosides of pyrrolopyridazines. 相似文献
10.
New convenient syntheses of 4,6-dimethyl[1,2,5]oxadiazolo[3,4-d]pyrimidine-5,7(4H,6H)-dione 1-oxide (I) from 1,3-dimethyl-6-hydroxylaminouracil by means of nitrosative and nitrative cyclizations are described. Compound I was converted into 4,6-dimethyl[1,2,5]oxadiazolo[3,4-d]pyrimidine-5,7(4H,6H)dione [4,6-dimethyl-5,7(4H,6H)furazano[3,4-d]pyrimidinedione] by refluxing in dimethylformamide. Transformation of I to 1,3,7,9-tetramethyl-2,4,6,8(1H,3H,7H,9H)pyrimido[5,4-g]pteridinetetrone and/or 1,3,6,8-tetramethyl-2,4,7,9(1H,3H,6H,8H)pyrimido[4,5-g]pteridinetetrone is described. 相似文献
11.
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
12.
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
13.
John W. Mcfarland William A. Essary Lale Cilenti William Cozart Philip E. Mcfarland 《Journal of heterocyclic chemistry》1975,12(4):705-707
Furo[3,2-c] pyridine (I) was nitrated to give 2-nitrofuro[3,2-c]pyridine (II). Bromination and chlorination of I gave, respectively, 2,3-dibromo-2,3-dihydrofuro[3,2-c]pyridine (III) and 2,3-dichloro-2,3-dihydrofuro[3,2-c]pyridine (IV). Oxidation of I with hydrogen peroxide afforded furo[3,2-c]pyridine 5-oxide (V) which was converted to I by phosphorus trichloride and to 4-chlorofuro[3,2-c]pyridine (VI) by phosphorus oxychloride. 相似文献
14.
Fedorov A. E. Rodinovskaya L. A. Shestopalov A. M. Sigeev A. S. 《Russian Chemical Bulletin》2021,70(2):394-405
A convenient method was developed for the combinatorial synthesis of substituted (5aS)-2-benzylthio-3-cyano-4,5a,6,7,8,10-hexahydro-5H-pyrrolo[1,2-a]thieno[3,2-e][1,4]-diazepine-5,10-diones. The structure and the most probable conformation of (5aS)-2-benzylthio-3-cyano-4,5a,6,7,8,10-hexahydro-5H-pyrrolo[1,2-a]thieno[3,2-e][1,4]diazepine-5,10-dione in solution was established by NMR spectroscopy and calculations using the Gaussian program.
相似文献15.
Dong Han Kim 《Journal of heterocyclic chemistry》1980,17(7):1647-1648
Synthesis of (4S,9aS)-hexahydro-4-methyl-1H,5H-pyrrolo[2,1-c][1,4]thiazepine-1,5-dione, an orally active potent angiotensin converting enzyme inhibitor is described. 相似文献
16.
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
17.
C. J. Shishoo M. B. Devani G. V. Ullas S. Ananthan V. S. Bhadti 《Journal of heterocyclic chemistry》1988,25(2):615-622
5H-Triazolo[1,5-d]- and 5H-tetrazolo[1,5-d]thieno[3,2-f]-1,4-diazepin-6(7H)-ones have been obtained by the base catalysed ring expansion reaction of 5-chloromethyl-1,2,4-triazolo[1,5-c]- and 5-chloromethyltetrazolo- [1,5-c]thieno[3,2-e]pyrimidines. The required thienopyrimidine derivatives were synthesized from 2-amino-3-triazolyl- and 2-amino-3-tetrazolylthiophenes by acylation, followed by dehydrative cyclization. 相似文献
18.
Vilsmeier–Haack formylation of 3-acetyl-1-methyl-4-hydroxyquinolin-2(1H)-one (2) produced the novel 6-methyl-4,5-dioxo-5,6-dihydro-4H-pyrano[3,2-c]quinoline-3-carboxaldehyde (3). Reactions of carboxaldehyde 3 with a diversity of nucleophilic reagents were studied and a variety of products were obtained via ring-opening, ring-closing (RORC) sequence. Also, some novel heteroannulated pyrano[3,2-c]quinolines were prepared. Structures of the new synthesized products were deduced on the basis of their analytical and spectral data. 相似文献
19.
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
20.
Palladium(0)/copper iodide catalyzed Sonogashira cross-coupling of 2-aryl-3-iodo-4-(phenylamino)quinolines with terminal alkynes afforded series of 1,2,4-trisubstituted 1H-pyrrolo[3,2-c]quinolines in a single-step operation. Conversely, the 4-(N,N-allylphenylamino)-2-aryl-3-iodoquinoline derivatives were found to undergo PdCl2(PPh3)2/CuI catalyzed intramolecular Heck reaction to yield the corresponding 1,3,4-trisubstituted 1H-pyrrolo[3,2-c]quinolines. 相似文献